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How to Get a Date Worth Keeping
It stinks, doesn’t it. But what can you do to fix it? More than you’ve ever imagined. You can put an end to the datelessness. Starting today—right now—you can begin a journey that will bring fun and interesting people into your life, broaden your experience of others and yourself, and lead you toward that date of all dates—a date worth keeping. This book is for YOU if · You want to get more dates or better dates. · You wonder where “the good ones” are. · You keep repeating the same old cycle in your dating life and want to change it. · You wonder why people who aren’t as nice as you get all the dates. · You’re attracted to the wrong kind, while the right kind lack the “chemistry.” · You’re waiting for God to bring you the right person—and you’ve been waiting an awfully long time. · You wonder what it is about you that fails to attract dates. With over ten years of experience personally coaching singles on dating, Dr. Henry Cloud shares his proven, very doable, step-by-step approach to overcoming your sticking points and getting all the dates you could want. The results speak for themselves. Filled with true-life examples you’ll identify with instantly, How to Get a Date Worth Keeping will prove its worth to you many times over in the exciting months ahead.
240 pages, Kindle Edition
First published September 1, 2004
231 people are currently reading
1488 people want to read
About the author
Henry Cloud
211 books2,175 followersDr. Cloud has written or co-written twenty-five books, including the two million-seller Boundaries. His most recent books are Boundaries for Leaders and Necessary Endings. He has earned three Gold Medallion awards, and was awarded the distinguished Retailers Choice award for God Will Make A Way.
As president of Cloud-Townsend Resources, Dr. Cloud has produced and conducted hundreds of public seminars around the country. He speaks on relationships—marriage, parenting, dating, personal growth, and spirituality. His seminars are often broadcast live to over two thousand venues at a time.
As president of Cloud-Townsend Resources, Dr. Cloud has produced and conducted hundreds of public seminars around the country. He speaks on relationships—marriage, parenting, dating, personal growth, and spirituality. His seminars are often broadcast live to over two thousand venues at a time.
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Displaying 1 - 30 of 222 reviews
January 20, 2012
This book is my favorite dating book, and I'm not even Xtian. Mostly as a joke, I checked this book (along with the very secular Four Man Plan) out of the library in 2008. These books ended up changing my approach to dating.
So often when I was on dates, I would feel distracted rather than being present with my date, as I tried to decide based on one or two or three dates whether I wanted to marry the person, and it's just not possible. Obviously there are some people who are right out, and there's no point in torturing yourself with bad dates with horrible conversation, but so many dates fall in the middle ground.
These two books encourage people to meet and date many people simultaneously and get to know their dates slowly without judgement. That patient, accepting, non-evaluative approach to dating really revolutionized my approach to dating. Rather than sitting there in judgement deciding whether my date was good enough, right for me, or anything else, I could be present with them and just get to know them. As a result, I met some wonderful people who felt accepted rather than judged, and as a result they trusted me. I probably became a more patient, accepting person in the rest of my life as well.
All people should be treated well, and yet often we treat people according to a subjective rating that we give them. That has a side-effect of making people we rate high feel self-conscious and people we rate low feel diminished, and neither feeling is particularly comfortable or conducive to intimacy. Especially since it's pretty arbitrary anyhow.
Three years after reading this book, I met my soulmate. I can't see myself with anyone else now, but I don't know if I would have given our relationship enough time to develop if I hadn't taken this patient approach, and this book helped in that.
So often when I was on dates, I would feel distracted rather than being present with my date, as I tried to decide based on one or two or three dates whether I wanted to marry the person, and it's just not possible. Obviously there are some people who are right out, and there's no point in torturing yourself with bad dates with horrible conversation, but so many dates fall in the middle ground.
These two books encourage people to meet and date many people simultaneously and get to know their dates slowly without judgement. That patient, accepting, non-evaluative approach to dating really revolutionized my approach to dating. Rather than sitting there in judgement deciding whether my date was good enough, right for me, or anything else, I could be present with them and just get to know them. As a result, I met some wonderful people who felt accepted rather than judged, and as a result they trusted me. I probably became a more patient, accepting person in the rest of my life as well.
All people should be treated well, and yet often we treat people according to a subjective rating that we give them. That has a side-effect of making people we rate high feel self-conscious and people we rate low feel diminished, and neither feeling is particularly comfortable or conducive to intimacy. Especially since it's pretty arbitrary anyhow.
Three years after reading this book, I met my soulmate. I can't see myself with anyone else now, but I don't know if I would have given our relationship enough time to develop if I hadn't taken this patient approach, and this book helped in that.
August 9, 2012
So I got REALLY mad at this book (and its writer). Most of the stuff in here is good, and I can tell a difference in life by doing some of it. HOWEVER - the meeting five guys a week task (to the point where they have your name and know how to contact you later) does not work for me. I get the concept and ya know what? If I could meet five guys a week by myself I wouldn't need to read this book, would I? It's always so easy for extroverts to say, "Hey, go meet people" but for the rest of us, that is like climbing Mt. Everest. And one of the participants said, "Being an introvert is not an excuse." Really? Ever been one?
I get being more open. I get not being afraid of people and putting yourself in the position to see and be seen. But I'm not going to change myself that much for a man. It would be like telling an overweight person to be skinny. And I have a feeling Dr. Cloud would say, "Well, then just be single for the rest of your life" (b/c he's kinda snarky like that in an attempt at humor, but most of if is kinda mean, honestly). Sorry, but if I'm following the path God has set for me, and yes, actively pursuing this task, then God won't let me miss someone b/c I might be too shy to go right over and give him my life story. Sorry Dr. Cloud, but God is bigger than that. I definitely need to do my part and not just wait for God to send me a guy BUT God made me exactly who I am, He knows exactly what I need, and I can't do God's part too.
Ok, wow, I was more frustrated with this one than I thought. The rest of his advice is pretty good. I did think that he should have maybe made the last section about fixing yourself (which he refers to constantly) first and THEN get to the dating stuff, but it all works out in the end.
Did this book help me? Yes, absolutely. It gave me a lot of food for thought and definitely reinforced my need to change my daily patterns. Did I want to punch the author once or twice? Yep. Shrug. Sorry.
I get being more open. I get not being afraid of people and putting yourself in the position to see and be seen. But I'm not going to change myself that much for a man. It would be like telling an overweight person to be skinny. And I have a feeling Dr. Cloud would say, "Well, then just be single for the rest of your life" (b/c he's kinda snarky like that in an attempt at humor, but most of if is kinda mean, honestly). Sorry, but if I'm following the path God has set for me, and yes, actively pursuing this task, then God won't let me miss someone b/c I might be too shy to go right over and give him my life story. Sorry Dr. Cloud, but God is bigger than that. I definitely need to do my part and not just wait for God to send me a guy BUT God made me exactly who I am, He knows exactly what I need, and I can't do God's part too.
Ok, wow, I was more frustrated with this one than I thought. The rest of his advice is pretty good. I did think that he should have maybe made the last section about fixing yourself (which he refers to constantly) first and THEN get to the dating stuff, but it all works out in the end.
Did this book help me? Yes, absolutely. It gave me a lot of food for thought and definitely reinforced my need to change my daily patterns. Did I want to punch the author once or twice? Yep. Shrug. Sorry.
March 20, 2008
When I was single, I read a number of Christian books on dating from what I can remember:
Passion and Purity by Elisabeth Elliot
Quest for Love also by Elisabeth Elliot
I Kissed Dating Goodbye by Joshua Harris
Lady in Waiting by Debbie Jones
Boundaries in Dating by Henry Cloud & John Townsend
...and one other book whose title I can't remember...
Of all of these books, I think Elliot's were the most inspiring to me. I appreciated her acknowledgement of the legitimacy of dating, but also her cautions from the heart. Most of the other books and their content sort of blend together in my mind in a jumble.
And then there's How to Get a Date Worth Keeping... which I actually read for the first time after I was married! It is definitely very different from all the other dating books I read. In this book, Henry Cloud not only acknowledges the legitimacy of dating, but pleads it cause.
There are some really good points contained in this book that a generation raised staunchly on an I Kissed Dating Goodbye mentality could do to be reminded of.
Early in the book Cloud presents his readers with a challenge. Meet 5 new people a week (either gender counts). And in order to count as one of your 5, you must exchange contact info. with that person.
What this does is it catapaults you out of the realm of the "Why am I not meeting anyone marriage-worthy?" into the realm of actually establishing relationships that God can develop into something greater.
Cloud makes the terrific point that a lot of our pious talk about "I'm not going to date someone unless he/she has such-and-such quality" is flawed and self-defeating. #1 -- You might be wrong about the type of person you think you will get along well with, or your preferences might actually change (think Green Eggs and Ham here), #2 -- You cannot judge a book by it's cover, and #3 -- You might actually be genuinely flawed in thinking you know "what's good for you" -- God knows these things much better than we do.
So, hence another of Cloud's challenges... Be willing to date anyone once (and maybe twice). I've talked to a number of single friends who cut themselves off from opportunities to simply grow socially (if nothing else) because they refuse to consider spending any time with someone who does not match their description of "My Perfect Spouse."
Of course this brings us to the highly controversial chapter in Cloud's book on "Dating Non-Christians." My husband and I actually fall on different sides of the fence on how we feel about this chapter. Suffice it to say that Cloud pushes the conservative Christian envelope on this one.
Regardless of how one feels about the controversial chapter here, this book is definitely one to add to your "dating bookshelf!" I think it's really important for Christian singles (teens and adults alike) to be exposed to Christian books on this topic from a wide variety of angles. Allow this one to "round out" your views and generate discussion with family & friends -- good stuff.
And finally, how I especially appreciated reading this book as a married woman... What a great challenge it offered to me (as a timid introvert) to get out there and meet people. 5 people a week is still not something I've been able to attain, but it's definitely a good reminder that people are so worth relating to.
Another incredibly important point that Cloud makes in this book is the absolute necessity of having a "support network" as you go into this adventure. I can't argue here. Again, I've met Christian singles who are trying to "go it alone" in the dating arena. Their dating life is such a private thing -- it's this one-man battle, this single-woman quest that must be done alone. Ideally, it shouldn't be that at all. You need to have a team of godly friends who are surrounding you, and who are willing to tell it like it is.
So, in summary, a really controversial book (one that created all sorts of lively discussion in our church's singles' group the semester we decided to read it together). But also a must-read that I highly recommend.
--Jen
Passion and Purity by Elisabeth Elliot
Quest for Love also by Elisabeth Elliot
I Kissed Dating Goodbye by Joshua Harris
Lady in Waiting by Debbie Jones
Boundaries in Dating by Henry Cloud & John Townsend
...and one other book whose title I can't remember...
Of all of these books, I think Elliot's were the most inspiring to me. I appreciated her acknowledgement of the legitimacy of dating, but also her cautions from the heart. Most of the other books and their content sort of blend together in my mind in a jumble.
And then there's How to Get a Date Worth Keeping... which I actually read for the first time after I was married! It is definitely very different from all the other dating books I read. In this book, Henry Cloud not only acknowledges the legitimacy of dating, but pleads it cause.
There are some really good points contained in this book that a generation raised staunchly on an I Kissed Dating Goodbye mentality could do to be reminded of.
Early in the book Cloud presents his readers with a challenge. Meet 5 new people a week (either gender counts). And in order to count as one of your 5, you must exchange contact info. with that person.
What this does is it catapaults you out of the realm of the "Why am I not meeting anyone marriage-worthy?" into the realm of actually establishing relationships that God can develop into something greater.
Cloud makes the terrific point that a lot of our pious talk about "I'm not going to date someone unless he/she has such-and-such quality" is flawed and self-defeating. #1 -- You might be wrong about the type of person you think you will get along well with, or your preferences might actually change (think Green Eggs and Ham here), #2 -- You cannot judge a book by it's cover, and #3 -- You might actually be genuinely flawed in thinking you know "what's good for you" -- God knows these things much better than we do.
So, hence another of Cloud's challenges... Be willing to date anyone once (and maybe twice). I've talked to a number of single friends who cut themselves off from opportunities to simply grow socially (if nothing else) because they refuse to consider spending any time with someone who does not match their description of "My Perfect Spouse."
Of course this brings us to the highly controversial chapter in Cloud's book on "Dating Non-Christians." My husband and I actually fall on different sides of the fence on how we feel about this chapter. Suffice it to say that Cloud pushes the conservative Christian envelope on this one.
Regardless of how one feels about the controversial chapter here, this book is definitely one to add to your "dating bookshelf!" I think it's really important for Christian singles (teens and adults alike) to be exposed to Christian books on this topic from a wide variety of angles. Allow this one to "round out" your views and generate discussion with family & friends -- good stuff.
And finally, how I especially appreciated reading this book as a married woman... What a great challenge it offered to me (as a timid introvert) to get out there and meet people. 5 people a week is still not something I've been able to attain, but it's definitely a good reminder that people are so worth relating to.
Another incredibly important point that Cloud makes in this book is the absolute necessity of having a "support network" as you go into this adventure. I can't argue here. Again, I've met Christian singles who are trying to "go it alone" in the dating arena. Their dating life is such a private thing -- it's this one-man battle, this single-woman quest that must be done alone. Ideally, it shouldn't be that at all. You need to have a team of godly friends who are surrounding you, and who are willing to tell it like it is.
So, in summary, a really controversial book (one that created all sorts of lively discussion in our church's singles' group the semester we decided to read it together). But also a must-read that I highly recommend.
--Jen
March 15, 2012
Kind of blew my mind. It is mostly about finding out who you are, making sure you are whole and drawing complete people to you. Learning how to be open to people while guarding your heart is applicable in any relationship in life. Also, I got 5 numbers in the first 2 days. It's a tough philosophy to be brave all the time. Maybe I will actually get a date worth keeping. In the meantime, it's interesting getting to know who I really am. I'm not actually lonely, undesirable or ugly. I'm fulfilled, interesting and beautiful and pursued by the Lord. I shall end with one of my favorite bible verses. Psalm 56:1 Be merciful to me, O God, for men hotly pursue me; all day long they press their attack.
Update. I have a first date with a terrific guy who loves Jesus and knows he is made complete in him. Guess I'm not getting te dollar back the the book cost me. Wahoo!
Update. I have a first date with a terrific guy who loves Jesus and knows he is made complete in him. Guess I'm not getting te dollar back the the book cost me. Wahoo!
Currently reading
September 21, 2009I dont think I am going to finish reading this book its making me mad becasue the author is bascially putting women down for waiting on God to bring them a man. He also acts like he has all the answers to getting people dates. In this book is a program where he asks the reader to do certain things like keep a log on how many guys they meet in a month and then add up the numbers and find out what is wrong with you for not getting lots of dates. There could be nothing wrong with you becasue if God wants you to date He will bring that person into your life when your ready according to God. This book has other issues that just irk me as well like saying the marriage is not the purpose of dating. Dating the worlds way isnt good. If u date a lot of people then when u are with the one you will wonder what your life would be like if u chose another person. all this breaking up and getting with someone else is like pratice for divoirce. I am mad at this book. It is a waste of trees.
December 3, 2025
Here are some things I’ve heard from other dating books or sermons
“You just gotta be running toward God, and then one day, you’ll look up, and someone will be running next to you, and then you can run hand in hand and get married”
“Kissing before marriage is not biblical and you should treat the girl you’re dating like your sister physically”
“You are a treasure, and you just need to keep digging the hole in which you are buried until someone eventually reaches you”
And I’m not even gonna go into the idea that dating for anything except marriage will only lead to sin and God will somehow tell you when you meet the right person.
All this to say - this book was a radical shift from the above and a perspective I, as a girl raised in purity culture and the southern Baptist church, had never even considered. Thinking of going on dates as getting in reps to figure out what works and what doesn’t? Mind blowing.
What’s even more wild is everything he said aligns with scripture! So it begs the question, what is the dating artifice we have created? Why have I, specifically as a women, been told I need to literally dig myself in a hole and wait?
Much to ponder but can’t recommend this enough
“You just gotta be running toward God, and then one day, you’ll look up, and someone will be running next to you, and then you can run hand in hand and get married”
“Kissing before marriage is not biblical and you should treat the girl you’re dating like your sister physically”
“You are a treasure, and you just need to keep digging the hole in which you are buried until someone eventually reaches you”
And I’m not even gonna go into the idea that dating for anything except marriage will only lead to sin and God will somehow tell you when you meet the right person.
All this to say - this book was a radical shift from the above and a perspective I, as a girl raised in purity culture and the southern Baptist church, had never even considered. Thinking of going on dates as getting in reps to figure out what works and what doesn’t? Mind blowing.
What’s even more wild is everything he said aligns with scripture! So it begs the question, what is the dating artifice we have created? Why have I, specifically as a women, been told I need to literally dig myself in a hole and wait?
Much to ponder but can’t recommend this enough
December 4, 2018
This book really sucks !It is condescending and patronizing ! How come that 99.99% of the people who sought help were women ?! Is it that men have no problems when it comes to dating or what ?!
I believe that this Dr.Cloud is a misogynist posing for a know-it-all !
I believe that this Dr.Cloud is a misogynist posing for a know-it-all !
December 26, 2023
A fresh perspective on dating from a biblical psychology perspective! Have had many fun convos with different friends around the ideas in here
February 3, 2011
I listened to the abridged audiobook version of Henry Cloud's How to Get a Date Worth Keeping. This version is much shorter than the unabridged book, and has a very crisp and efficient feel. I'm not normally a fan of abridged books, but this one really works. The author reads the book himself and does an excellent job. He's very enthusiastic and personable.
I almost didn't submit a review for this book. Since the whole point of the book is to give a practical approach to dating it doesn't seem fair to evaluate it without trying out the method. Since I'm married, that's not really an option. But as someone who is frequently counseling young Christian singles I need to have some opinion on it, so I'm going to give it a tentative 4 stars.
Cloud dispels a lot of the myths Christians have which hurt their ability to date well, especially the idea that you should just sit and wait for God to bring you your special someone (a bizarre American mixture of predestination and romance that is completely un-Biblical and theologically illogical). If that's your committed theology on relationships, as it appears to be for at least one other reviewer, this book is just going to make you mad. Instead, Cloud advocates an approach to dating casually, dating as many people as possible, and using the process to figure out what kind of person you want to be with as well as to grow as a person yourself. For him, thoughtful casual dating can be a means of dealing with the issues that have been crippling a person's ability to meet people or to date the right kinds of people. And he gives much practical advice for how to do this well, successfully, and with Christian integrity. It actually makes a lot of sense--a lot more than the typical Christian approach of getting into a serious relationship with the first person you connect with and then marrying them by default or working at it for a couple of years until you painfully break up. Again, I don't know how well Cloud's system works in practice, but his approach certainly deserves to be considered and provides a unique and helpful counterpoint to other Christian dating philosophies.
If Cloud's book has any obvious weak points they are these: he makes everything he says sound surefire and easy, which is encouraging and motivational, but also maybe a bit misleading. I know one person who got a bit worn out trying this dating method. My second critique is that he sometimes makes theologically questionable statements about dating in order to back up his practical advice. Example: Cloud makes a big point of saying that dating is NOT about finding someone to marry. Practically, his point is very sound. If you go into every date trying to land a spouse you're not going to be able to be objective, or date a variety of people, or be natural and comfortable. But theologically, there's no way you can back up that statement. There is no dating in the Bible, only engagement/marriage and singleness. Biblically speaking romance IS all about marriage, ultimately. There is no sense that God gave us dating (like he did marriage) or that his people should devote a great deal of effort to finding a date. Cloud would have been on more solid ground if he argued that dating is about finding a spouse ultimately, but that it only works if you relax and let go of the possibility of future marriage to make good use of dating in the present. Also it's nearly impossible to reconcile Cloud's approach to dating with Paul's advice about remaining single to serve God in 1 Corinthians 7. He never deals with the Biblical concept of preferring singleness to marriage, which would ultimately be the most challenging and prophetic thing you could say in our romance-obsessed culture.
Still, in a cultural context where dating is the best and only way to find a spouse, and where no really good Christian alternatives exist (sorry "courtship" advocates, it just ain't gonna happen) this may be an essential piece of reading for those who would like to find a strong Christian life partner. I definitely recommend reading it and considering it along with the other input you're getting on your dating life. However, if any of you are trying it and have other thoughts, please comment. I'd love to hear what you think.
I almost didn't submit a review for this book. Since the whole point of the book is to give a practical approach to dating it doesn't seem fair to evaluate it without trying out the method. Since I'm married, that's not really an option. But as someone who is frequently counseling young Christian singles I need to have some opinion on it, so I'm going to give it a tentative 4 stars.
Cloud dispels a lot of the myths Christians have which hurt their ability to date well, especially the idea that you should just sit and wait for God to bring you your special someone (a bizarre American mixture of predestination and romance that is completely un-Biblical and theologically illogical). If that's your committed theology on relationships, as it appears to be for at least one other reviewer, this book is just going to make you mad. Instead, Cloud advocates an approach to dating casually, dating as many people as possible, and using the process to figure out what kind of person you want to be with as well as to grow as a person yourself. For him, thoughtful casual dating can be a means of dealing with the issues that have been crippling a person's ability to meet people or to date the right kinds of people. And he gives much practical advice for how to do this well, successfully, and with Christian integrity. It actually makes a lot of sense--a lot more than the typical Christian approach of getting into a serious relationship with the first person you connect with and then marrying them by default or working at it for a couple of years until you painfully break up. Again, I don't know how well Cloud's system works in practice, but his approach certainly deserves to be considered and provides a unique and helpful counterpoint to other Christian dating philosophies.
If Cloud's book has any obvious weak points they are these: he makes everything he says sound surefire and easy, which is encouraging and motivational, but also maybe a bit misleading. I know one person who got a bit worn out trying this dating method. My second critique is that he sometimes makes theologically questionable statements about dating in order to back up his practical advice. Example: Cloud makes a big point of saying that dating is NOT about finding someone to marry. Practically, his point is very sound. If you go into every date trying to land a spouse you're not going to be able to be objective, or date a variety of people, or be natural and comfortable. But theologically, there's no way you can back up that statement. There is no dating in the Bible, only engagement/marriage and singleness. Biblically speaking romance IS all about marriage, ultimately. There is no sense that God gave us dating (like he did marriage) or that his people should devote a great deal of effort to finding a date. Cloud would have been on more solid ground if he argued that dating is about finding a spouse ultimately, but that it only works if you relax and let go of the possibility of future marriage to make good use of dating in the present. Also it's nearly impossible to reconcile Cloud's approach to dating with Paul's advice about remaining single to serve God in 1 Corinthians 7. He never deals with the Biblical concept of preferring singleness to marriage, which would ultimately be the most challenging and prophetic thing you could say in our romance-obsessed culture.
Still, in a cultural context where dating is the best and only way to find a spouse, and where no really good Christian alternatives exist (sorry "courtship" advocates, it just ain't gonna happen) this may be an essential piece of reading for those who would like to find a strong Christian life partner. I definitely recommend reading it and considering it along with the other input you're getting on your dating life. However, if any of you are trying it and have other thoughts, please comment. I'd love to hear what you think.
December 30, 2017
I don’t review books very often, but I will this one, even though there is only one thing I can concretely recall from the book.
“Meet five people a week who want to date you” but, wait, five people you met don’t want to date you? Then you’ve failed. It isn’t the practices of the book, but you the reader who clearly cannot be saved from the empty void that is your romantic life.
If I could meet five people a week who wanted to date me, I wouldn’t need to purchase or read this book. I had read this book expecting help, not condemnation.
So, in short, since I can’t meet any woman willing to date me, I’m clearly a failure as a human and his advice is still the inerrant word on relationships according to his reasoning.
I thought it would be helpful in offering thoughts and ideas on how to search/understand dating and what to look for in relationships, while also giving areas to reflect upon my own personality as it pertains to dating. Instead it just critiqued me as a person without actually enlightening anything about my life or search.
I thought it would offer helpful thoughts so I could reflect on what I do, could do, and could try to do in dating, but instead it offered condemnation over assistance and reflection.
I wish that I could remember more from it, but I can’t recall specifics. Only that it was condescending, and was written by someone who hasn’t been in the dating world in a very long time.
“Meet five people a week who want to date you” but, wait, five people you met don’t want to date you? Then you’ve failed. It isn’t the practices of the book, but you the reader who clearly cannot be saved from the empty void that is your romantic life.
If I could meet five people a week who wanted to date me, I wouldn’t need to purchase or read this book. I had read this book expecting help, not condemnation.
So, in short, since I can’t meet any woman willing to date me, I’m clearly a failure as a human and his advice is still the inerrant word on relationships according to his reasoning.
I thought it would be helpful in offering thoughts and ideas on how to search/understand dating and what to look for in relationships, while also giving areas to reflect upon my own personality as it pertains to dating. Instead it just critiqued me as a person without actually enlightening anything about my life or search.
I thought it would offer helpful thoughts so I could reflect on what I do, could do, and could try to do in dating, but instead it offered condemnation over assistance and reflection.
I wish that I could remember more from it, but I can’t recall specifics. Only that it was condescending, and was written by someone who hasn’t been in the dating world in a very long time.
This entire review has been hidden because of spoilers.
February 14, 2014
Having grown up in the I Kissed Dating Goodbye era, this book actually offers practical advice on dating, relationships, and how to grow in character. It's a book I wish I would have read years ago.
Often Christian dating books are written by pastors pretending to be psychologists, whereas Henry Cloud is a one and offers real insights into how dating can help you grow.
Often Christian dating books are written by pastors pretending to be psychologists, whereas Henry Cloud is a one and offers real insights into how dating can help you grow.
August 9, 2022
I picked up this book because an adult that I trust has been wanting to read it but she hasn't had the chance. She has liked other life coaching books by this author, so I thought that I should give it a try.
To be honest...I didn't like this book because most of the tips in the book didn't apply to me.
This book is for someone in their mid twenties to early thirties who doesn't go out of their way to meet new people or talk to new people. For someone who doesn't understand why they can't get dates. For someone who doesn't get asked out or doesn't ask out that many people.
I'm an extroverted person and I love talking to random new people, and so I don't have a problem expanding my social circle. I've also watched a lot of The Amazing Race and Survivor, and these reality tv shows have taught me a lot about different types of people and how people react under pressure in stressful situations. I've analyzed what healthy relationships look like and how and why they work. I'm not actively looking for a boyfriend - I picked up this book mainly for the "date worth keeping" part, not the "how to get a date" part.
The main premise of this book is that dating is NOT about marriage - it's about meeting new people, learning more about yourself in the process, and growing and changing. You shouldn't have a list of pre-requisites before you go out with someone. You should go out with all sorts of people. Dating should just be doing fun and meaningful things with cool people, not to marry.
I had a problem with this because I feel that's what FRIENDS are for. FRIENDS hang out and have fun and do meaningful things together because they enjoy each other's company. So basically I have a different definition of the word "dating."
The book said that sometimes it's fine for a Christian to go out with non Christians because dating is not about finding someone to marry. The book says that if you date a non Christian, you don't have to worry about your heart being too broken because if God is the most important thing in your life, then you aren't in danger of falling in love with a non Christian because God isn't in the non Christian's heart. I completely disagreed with this point. I don't want to put myself in a position to hurt myself or to hurt others because one of the most essential requirements about a potential partner (for me) is missing. I feel like you have to be a very mature adult and Christian to be able to guard your heart THAT much and to not be in danger of falling in love with a non Christian. Personally, I wouldn't put myself in that position.
The book said that even if you like someone to the point where you think it has long term potential, still don't be exclusive. So basically, you can go out with a lot of people at once. I have a problem with this because I would only go out with someone on a date if I wanted to be exclusive with them. I get to know people as friends, and if I like a particular person more than a friend, then I would want to just go out with that one particular person. I would want to stay true to someone, you know?
Even though I didn't agree with the above, there were a few points that I liked (although I already knew almost all of it):
Love at first sight doesn't exist. Love and infatuation are different, and many people get them confused. Love is when you commit to each other, you resolve conflict, you sacrifice and forgive, you give and you share values. Building these things up take time.
A relationship should be evaluated based on what you VALUE rather than how attached you are to someone. What are you looking for? Someone honest, loving, responsible, spiritually committed, able to value the relationship, respect your interests and his own, respectful of boundaries, and lives out spiritual values.
You're ready to date if you're happy being single. You have to be a WHOLE person on your own. Don't look for someone to "complete" you. You're more attractive anyway if you're a whole person. Focus on yourself instead of focusing on finding someone.
Sex before marriage can be destructive if it's part of dating life. God is not some killjoy - He's trying to protect you. Sex before marriage is giving 100% of your body to someone else, but then less than 100% of the rest of them (their heart, soul, mind, life, etc). God wants the basis of sex to be LOVE.
Guard your heart, and only give your heart to someone who deserves it. A relationship should be focused on God and you should want to seek God together.
The end of the book had a lot of questions that you should ask yourself about someone you're getting serious with. Those questions can be helpful.
Overall, this book is for someone who is still trying to become a whole person themselves, and who doesn't meet that many new people or potential dates. This book wasn't helpful for me, but I still read it all the way through so that I wouldn't miss anything. I gave it 3/5 stars instead of 1/5 stars because it could be helpful for other people.
I don't think I'm going to change much about my approach to dating. I'm not interested in having a goal of meeting five new guys a week, or dating multiple people at once. I feel like I know myself pretty well - whenever I meet a new guy, I already analyze the reasons why we would or wouldn't work if we were a couple (even if I would never see them in THAT way to begin with). I love meeting new people (ENFJ!) and I'll continue to do that. It was cool to see a Christian perspective on dating (this was my first time reading a life coaching book), but it wasn't helpful for me.
To be honest...I didn't like this book because most of the tips in the book didn't apply to me.
This book is for someone in their mid twenties to early thirties who doesn't go out of their way to meet new people or talk to new people. For someone who doesn't understand why they can't get dates. For someone who doesn't get asked out or doesn't ask out that many people.
I'm an extroverted person and I love talking to random new people, and so I don't have a problem expanding my social circle. I've also watched a lot of The Amazing Race and Survivor, and these reality tv shows have taught me a lot about different types of people and how people react under pressure in stressful situations. I've analyzed what healthy relationships look like and how and why they work. I'm not actively looking for a boyfriend - I picked up this book mainly for the "date worth keeping" part, not the "how to get a date" part.
The main premise of this book is that dating is NOT about marriage - it's about meeting new people, learning more about yourself in the process, and growing and changing. You shouldn't have a list of pre-requisites before you go out with someone. You should go out with all sorts of people. Dating should just be doing fun and meaningful things with cool people, not to marry.
I had a problem with this because I feel that's what FRIENDS are for. FRIENDS hang out and have fun and do meaningful things together because they enjoy each other's company. So basically I have a different definition of the word "dating."
The book said that sometimes it's fine for a Christian to go out with non Christians because dating is not about finding someone to marry. The book says that if you date a non Christian, you don't have to worry about your heart being too broken because if God is the most important thing in your life, then you aren't in danger of falling in love with a non Christian because God isn't in the non Christian's heart. I completely disagreed with this point. I don't want to put myself in a position to hurt myself or to hurt others because one of the most essential requirements about a potential partner (for me) is missing. I feel like you have to be a very mature adult and Christian to be able to guard your heart THAT much and to not be in danger of falling in love with a non Christian. Personally, I wouldn't put myself in that position.
The book said that even if you like someone to the point where you think it has long term potential, still don't be exclusive. So basically, you can go out with a lot of people at once. I have a problem with this because I would only go out with someone on a date if I wanted to be exclusive with them. I get to know people as friends, and if I like a particular person more than a friend, then I would want to just go out with that one particular person. I would want to stay true to someone, you know?
Even though I didn't agree with the above, there were a few points that I liked (although I already knew almost all of it):
Love at first sight doesn't exist. Love and infatuation are different, and many people get them confused. Love is when you commit to each other, you resolve conflict, you sacrifice and forgive, you give and you share values. Building these things up take time.
A relationship should be evaluated based on what you VALUE rather than how attached you are to someone. What are you looking for? Someone honest, loving, responsible, spiritually committed, able to value the relationship, respect your interests and his own, respectful of boundaries, and lives out spiritual values.
You're ready to date if you're happy being single. You have to be a WHOLE person on your own. Don't look for someone to "complete" you. You're more attractive anyway if you're a whole person. Focus on yourself instead of focusing on finding someone.
Sex before marriage can be destructive if it's part of dating life. God is not some killjoy - He's trying to protect you. Sex before marriage is giving 100% of your body to someone else, but then less than 100% of the rest of them (their heart, soul, mind, life, etc). God wants the basis of sex to be LOVE.
Guard your heart, and only give your heart to someone who deserves it. A relationship should be focused on God and you should want to seek God together.
The end of the book had a lot of questions that you should ask yourself about someone you're getting serious with. Those questions can be helpful.
Overall, this book is for someone who is still trying to become a whole person themselves, and who doesn't meet that many new people or potential dates. This book wasn't helpful for me, but I still read it all the way through so that I wouldn't miss anything. I gave it 3/5 stars instead of 1/5 stars because it could be helpful for other people.
I don't think I'm going to change much about my approach to dating. I'm not interested in having a goal of meeting five new guys a week, or dating multiple people at once. I feel like I know myself pretty well - whenever I meet a new guy, I already analyze the reasons why we would or wouldn't work if we were a couple (even if I would never see them in THAT way to begin with). I love meeting new people (ENFJ!) and I'll continue to do that. It was cool to see a Christian perspective on dating (this was my first time reading a life coaching book), but it wasn't helpful for me.
February 1, 2023
It was alright lol, had some fair points which challenged my thinking on things which is good. Definitely felt myself skimming over other parts. I’m not the target demographic though. I talk to girls all the time, right guys?
November 8, 2025
Whether or not you are a Christian I would highly recommend reading this book! I feel like it personally took a lot of anxiety and overthinking out of the dating experience!
May 24, 2023
What’s with all these religious books about dating?
Most of the advice in here is actually better than the other stuff I’ve read. Look inward, put yourself in situations where you can meet people. you will attract what you put out. Sure, great advice. Helpful.
I would say 60%-70% of it is good. And then sprinkled in are some land mines of weird puritanical nonsense. There is this strange need to control what people do with their bodies and sex lives. That combined with the weird self confirmatory, anecdotal nature of most of the advice here, means that this book is kind of like playing soccer in a war zone. Most of it’s fun, healthy even. And then, bam, landmine, and you’re missing a leg.
Most of the advice in here is actually better than the other stuff I’ve read. Look inward, put yourself in situations where you can meet people. you will attract what you put out. Sure, great advice. Helpful.
I would say 60%-70% of it is good. And then sprinkled in are some land mines of weird puritanical nonsense. There is this strange need to control what people do with their bodies and sex lives. That combined with the weird self confirmatory, anecdotal nature of most of the advice here, means that this book is kind of like playing soccer in a war zone. Most of it’s fun, healthy even. And then, bam, landmine, and you’re missing a leg.
May 2, 2025
Not too novel: but good emphasis for people to be aware on things to work on.
In simple align yourself with the words of the Bible and you’ll be set. Focus on continuous improvement in all areas of your life, love God, Neighbor, and self. Be available and sociable.
In simple align yourself with the words of the Bible and you’ll be set. Focus on continuous improvement in all areas of your life, love God, Neighbor, and self. Be available and sociable.
July 8, 2018
If you are frustrated in your dating life and want to grow and change as a person while getting a new mindset on what dating can be, I HIGHLY recommend this book.
I also HIGHLY recommend not reading this book alone. Read it with friends and encourage each other, hold each other accountable and do what it says. It will make a big difference.
Dating and growing are both difficult, but worthwhile endeavors.
I loved the scientific and Biblical view points shared in this book on dating.
Years ago I tried reading it, but I wasn’t ready to hear or do what it said. Now I am in a place to do that and I devoured the first 40 pages and then asked some other friends to read it with me and pray together.
I recommend doing that! It was so helpful.
Dating is a way to have fun and figure out what you really want. It’s a way for you to grow as a person and serve others by treating them well.
While rejection-I’m learning-is just part of the process, dating can be a fun/scary/stretching adventure.
Why are you still reading this review? Get off your booty, grab a couple of single friends and read this book!
I also HIGHLY recommend not reading this book alone. Read it with friends and encourage each other, hold each other accountable and do what it says. It will make a big difference.
Dating and growing are both difficult, but worthwhile endeavors.
I loved the scientific and Biblical view points shared in this book on dating.
Years ago I tried reading it, but I wasn’t ready to hear or do what it said. Now I am in a place to do that and I devoured the first 40 pages and then asked some other friends to read it with me and pray together.
I recommend doing that! It was so helpful.
Dating is a way to have fun and figure out what you really want. It’s a way for you to grow as a person and serve others by treating them well.
While rejection-I’m learning-is just part of the process, dating can be a fun/scary/stretching adventure.
Why are you still reading this review? Get off your booty, grab a couple of single friends and read this book!
January 7, 2013
A family member bought me this shortly after I went through a break up. Although I didn't necessarily relate to every single lesson in each chapter, I really enjoyed this! It opened up my eyes to habits I have that may prevent me from meeting a potential someone. For example, I tend to go for certain types of guys and sometimes write-off other "types" of people right away without even giving them a chance. One of the most helpful chapters in this book talks about becoming the person who you are looking for's ideal mate. What that basically means is... what do you have to offer a potential mate?
Probably the best part of this book for me was the format/style. There's a lot of narration as well as real stories from people throughout the chapters who have tried the techniques presented by Cloud.
Probably the best part of this book for me was the format/style. There's a lot of narration as well as real stories from people throughout the chapters who have tried the techniques presented by Cloud.
January 22, 2022
It is so bad I want to give you a zero, but that’s not possible, so I give you a one
I read boundaries in dating by Henry Cloud and John Townsend and I actually found it okay with some thought provoking information. So in the interest of self improvement I thought I’d read this too.
Big mistake. It was awful. He lost me as soon as he said single people should be dating five new people every week and told introverts to get over themselves if they think that would be too much for them. Sadly he didn’t redeem himself from there
He infers that there must be something wrong with people if they’re single and he also said you should get a friend to tell you in what ways you’re unattractive physically (and in other ways).
I don’t even want to donate this book in case someone else has the misfortune of reading it, it deserves to go straight into the bin.
I read boundaries in dating by Henry Cloud and John Townsend and I actually found it okay with some thought provoking information. So in the interest of self improvement I thought I’d read this too.
Big mistake. It was awful. He lost me as soon as he said single people should be dating five new people every week and told introverts to get over themselves if they think that would be too much for them. Sadly he didn’t redeem himself from there
He infers that there must be something wrong with people if they’re single and he also said you should get a friend to tell you in what ways you’re unattractive physically (and in other ways).
I don’t even want to donate this book in case someone else has the misfortune of reading it, it deserves to go straight into the bin.
December 23, 2016
Title is cheesy af, but it's actually a pretty great book. Unlike the many Christian books that philosophize about dating, or the many secular websites full of thinly veiled pick-up artistry, this book gets practical without encouraging denigration of the opposite sex.
The advice has a bit of an extroverted bias, but it's worth considering at least as a challenge. For example, I definitely never had 5 number-worthy conversations in a week, but I did make an effort to talk to five new people, which was pretty out-of-the-box for me.
Would recommend to any discouraged single person, especially if they've been influenced by I Kissed Dating Goodbye or similar "you must date only THE ONE" philosophy.
The advice has a bit of an extroverted bias, but it's worth considering at least as a challenge. For example, I definitely never had 5 number-worthy conversations in a week, but I did make an effort to talk to five new people, which was pretty out-of-the-box for me.
Would recommend to any discouraged single person, especially if they've been influenced by I Kissed Dating Goodbye or similar "you must date only THE ONE" philosophy.
April 10, 2008
Lately I've been driving myself crazy with dating books, but this book is pretty solid. Definitely worth picking up. I guess the one big takeaway for me was that if you date someone you normally wouldn't consider (given that they are a safe person) you could really learn something about yourself and maybe even discover something you'd like about a person you never thought you would (or didn't like).
July 9, 2019
I thought this was a good book with some interesting ideas. I like the approach to dating as a way to connect with God, and learn more about yourself and the areas that you need spiritual growth. I especially like the advice about having a strong support system of friends, mentors, and church family to advise and encourage you through the dating process.
This book has some wonderful Godly and Biblical guidance about dating and growing as a person.
This book has some wonderful Godly and Biblical guidance about dating and growing as a person.
August 23, 2023
I have genuinely never been so deeply challenged and also freed by a book that deals seriously with romantic relationships. Books on this topic tend to make me mad especially when it’s a Christian book that makes dating and marriage seem like prison. But this one was drastically different. Through each chapter I could feel the chains and lies in my mind on this subject melt or break away and I am left with a very different perspective on both dating and marriage.
October 3, 2018
I had several trusted people recommend this book, and because of that I was surprised about my initial negative feelings towards it. As I pushed through though, I definitely learned a few things and appreciated the book for what it was. I would describe it as the counterpoint view to I Kissed Dating Goodbye or similar narratives.
October 7, 2017
This is the best book on dating that I have ever read, and I've read a LOT of dating books. Dr. Cloud gives a real, practical and frank look at how to date in a realistic and healthy way. I cannot recommend this book highly enough, it has challenged and change my dating perspective in the best way.
January 21, 2010
Some good suggestions in this book, but I left it feeling like something is wrong with me because I am still single.
March 17, 2025
I had no idea that Dr. Henry Cloud wrote a dating book. I’ve read “Boundaries” and have read a lot of the modern Christian dating books in the past. I must have missed this one. This book covers a broad range of topics from dating in community (aka having a team) to not limiting yourself to a type to dating online (there are a lot more topics). Overall, I knew a lot of the information he wrote about from previous books and Christian dating podcasts, but it was actually a nice refresher. He had 2 hot takes that were really intriguing - 1) Dating is Not About Marriage 2) It’s okay to date a non-Christian (didn’t say marry).
Cloud has counseled a lot of people who put too much pressure on dating for the main purpose of marriage. He says that the purpose of dating is simply get to know someone and discover who they are. It is also about “learning what you need and want, and how you need to grow and change.” I like this approach/mindset because it takes the pressure off dating. I try to not put pressure on first dates, but sometimes it happens. Of course, you hope that you find the right person and you get married at the end of your dating season, but dating is supposed to be fun and a learning experience.
Cloud mentions that it’s okay to date a non-Christian because you’re not marrying that person right then and there. He gave an example of a couple - she was vocal about her faith and she brought her date to church and he chose to become a Christian. He mentions that he is not encouraging “missionary dating.”
I like how he mentions that dating is a risk and it is kind of like a numbers game. It’s inevitable that you’re going to face rejection in dating. I like that he mentioned that dating is work, kind of like marriage, school, and relationships, if you want to get the best possible result, you have to put the work into it.
Overall, great book on dating.
Cloud has counseled a lot of people who put too much pressure on dating for the main purpose of marriage. He says that the purpose of dating is simply get to know someone and discover who they are. It is also about “learning what you need and want, and how you need to grow and change.” I like this approach/mindset because it takes the pressure off dating. I try to not put pressure on first dates, but sometimes it happens. Of course, you hope that you find the right person and you get married at the end of your dating season, but dating is supposed to be fun and a learning experience.
Cloud mentions that it’s okay to date a non-Christian because you’re not marrying that person right then and there. He gave an example of a couple - she was vocal about her faith and she brought her date to church and he chose to become a Christian. He mentions that he is not encouraging “missionary dating.”
I like how he mentions that dating is a risk and it is kind of like a numbers game. It’s inevitable that you’re going to face rejection in dating. I like that he mentioned that dating is work, kind of like marriage, school, and relationships, if you want to get the best possible result, you have to put the work into it.
Overall, great book on dating.
December 18, 2024
If I had read the description first, I wouldn’t have read this book because it was HEAVY on the God-talk. It’s also been 20 years since it was written and that was very apparent. The writing towards the end was pissing me off as well as the outdated voice, so I literally skipped a whole chapter that I knew would enrage me. That being said, I do think it had some interesting perspectives and good advice for people getting back into the dating scene.
I actually deducted a star upon reflection because at the end he talked about “only dating adults” and basically said that any adult who still lived with their parents was not considered an adult and is a red flag. Pmo
I actually deducted a star upon reflection because at the end he talked about “only dating adults” and basically said that any adult who still lived with their parents was not considered an adult and is a red flag. Pmo
This entire review has been hidden because of spoilers.
March 13, 2019
Super practical and realistic! This book contains truths that are greatly needed for generations that were raised to "kiss dating goodbye." So many people avoid dating because our hookup and internet culture has fostered unhealthy patterns, but this book gives some really simple, practical advice for how to date in a clear and healthy way that honors God, honors other people, honors yourself, and DOESN'T rush into things just because you want to be married (recipe for disaster!). And like Dr. Cloud's other books, it has implications for the rest of life as well as for the topic at hand.
January 2, 2023
Though I’m no longer in the target audience, it’s a book I purchased and had not yet read when I had been in the intended audience. It might seem strange to read it as someone whose now married but the money had already been spent & I thought it still might be interesting to see if there’s some pockets of wisdom relevant to not only those looking to find a quality date. I didn’t read each and every section, but did read a fairly large amount. I didn’t always agree with everything Cloud had to say but there were plenty of highlights I made (aka noted pockets of wisdom).
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