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Jameson
Being a twenty-two-year-old virgin was not on my list of life goals. I don't know how it happened. Well...I never date, dedicate all my time to college, and I'm awkward with a capital A around hot guys--okay, so I know exactly how it happened. When my best friends come up with a plan to make the most of this summer before grad school, I'm all for it. That's how I end up at a charity bachelor auction, bidding on a date I hope will help me toss this V-card out the window.

What could possibly go wrong?

Will
Life is good. I love my new job as PA to the owner of a major production company. Being a prize in a charity auction and scoring the highest bid? Icing on the cake. Now I get to be the date of the most adorable, rambling, bow-tie-wearing grad student I've ever seen. Seriously, I can't be within ten feet of this guy without a smile on my face. When he slips that he's looking for a summer fling to experiment with, I'm game. Jameson is so different from anyone I've hooked up with before, so completely himself, I'm immediately smitten.

Oh, and did I mention we find out he's my boss's son?

Between keeping our fling-turned-relationship a secret from his dad and another little familial bombshell that gets dropped in our laps, I'm quickly learning that love is a whole lot more complicated than I thought.

218 pages, Kindle Edition

First published September 7, 2020

193 people are currently reading
468 people want to read

About the author

Riley Hart

114 books7,133 followers
Riley Hart is the girl who wears her heart on her sleeve. She's a hopeless romantic. A lover of sexy stories, passionate men, and writing about all the trouble they can get into together. If she's not writing, you'll probably find her reading.

Riley lives in California with her awesome family, who she is thankful for everyday.

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5 stars
441 (41%)
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434 (41%)
3 stars
149 (14%)
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30 (2%)
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Displaying 1 - 30 of 132 reviews
Profile Image for ~✡~Dαni(ela) ♥ ♂♂ love & semicolons~✡~.
3,594 reviews1,139 followers
November 8, 2020
"Seriously. We were cute as fuck."

That about sums it up. This book is adorable & steamy too.

Jamison is awkward and insecure about his virginity (he is 22, after all), but his rambling and lip biting just turn Will on more.

Will is not one for long-term commitments. He's outgoing, funny, and charming. But Jamison calls to him like a siren song.

Highlights include:

~ summer fling to something real

~ family dynamics (how amazing is Jamison's dad seriously?)

~ steamy first time (Jamison wants to try it all with Will)

~ mild angst (Will is Jamison's dad's PA, something the guys don't realize when they first meet via a bachelor charity auction)

~ some miscommunication, but not too much (eventually, both men admit they want more than casual)

~ the way Jamison stands up to Will's brothers (a scene worth waiting for)

~ Black MC (hurray!) & biracial relationship (I cannot even express how much I love diversity in romance: non-white MCs, disabled MCs, older MCs - YES, please)

~ HEA

We met Will in the first book, but I think Awkward Love works as a standalone.

4/5 recommended!
Profile Image for Imme [trying to crawl out of hiatus] van Gorp.
792 reviews1,951 followers
August 17, 2025
|| 3.0 stars ||

Just like the first book in the series, this was a sweet and cute read, but it wasn’t anything special.
Something about these books just does not manage to hit deep, but luckily they do succeed in giving me butterflies from time to time.

Jameson’s general shyness and constant rambling was all very endearing, and I definitely loved Will’s complete acceptance and utter adoration of him. They were honestly really good together, and I liked them as a couple.

There wasn’t any real drama between them, which was maybe slightly boring, but it did show how well they worked in a relationship. Of course there were still insecurities and problems along the way, and we also stuck with the whole “this is just a fling” thing for quite some time, but it was always obvious they were going to choose each other in the end and that they were really happy with that decision.

This is a super easy and light read with some adorable characters and a very sweet romance, but does not offer much more than that.


'Stumbling into Love' series:
1. Stupid Love - 3.0 stars
2. Awkward Love - 3.0 stars

Other Riley Hart books:
Broken Pieces - 3.5 stars
Finding Finley - 1.5 stars
‘Havenwood’ series - var. ratings
‘Atlanta Lightning’ series - var. ratings
Boyfriend Goals - 3.5 stars
Rookie Move - 4.0 stars
Playing Games - 4.0 star
The Hookup Mix-up - 2.0 stars
Profile Image for .Lili. .
1,275 reviews276 followers
September 9, 2020
Awkward Love by Riley Hart is the kind of read I love.

-Loveable main characters
-Opposites attract. Jameson and Will are complete opposites who fit and compliment each other.
-Family drama. It never gets too much, though, and is handled well.
-Low angst, feel good
-Chemistry

This book is a joy to read.


Profile Image for Susan.
2,349 reviews460 followers
January 8, 2021
Re-read January 2021

Still a fun story without any angst.

------------------------------------

This was very cute.

I really liked shy and awkward Jameson. And I thought Will was just perfect for him.

I really liked that despite them both saying it was 'just a fling' they didn't really stick to it. There was a part where I thought they would drag out the not talking about feelings thing, but luckily Jameson blurted out he wanted to be real boyfriends right after that, so all was good.

Overall this was really nice.
Profile Image for Gustaf.
1,444 reviews197 followers
February 11, 2021
THIS IS THE CUTEST BOOK EVER!!

I LOVED IT!!

Okay, I'm done screaming now, I just had to say it. I had to read this one after listening to the guys on The Big Gay Fiction Podcast talking about it. Knowing I probably would love it. And well I did.

Will and Jameson were perfect for each other. Jameson, the awkward, nerdy guy gave us most of the laughs. His rambling was adorable. Will is confident and sure of himself but has this insecure side, he's guarding close to his heart. Together they supported each other unconditionally and what follow is the sweetest book. I have the biggest, goofiest smile on my face writing this review. Now I have to go back and read the first book in the series.
Profile Image for Simona.
679 reviews63 followers
September 19, 2022
A low angst story. Plus the boss's son is always a good trope!

Really sweet
Profile Image for Kaity.
2,003 reviews24 followers
September 19, 2022
3.5 stars

Very cute! Will and Jameson were adorable. They made me smile and there some awkward cringe moments but overall an easy low angst read!

I am interested to see how Danny and Jonathan’s book plays out! Haha
Profile Image for Rachel Emily.
4,474 reviews380 followers
September 14, 2020
OMG this story was just ADORABLE! But it also hit me with all the feels and got me teary eyed, too!

I read this without having read the first book in the series (I thought this was book 2 of a different series, which I realize it's not but anyway...) so it was easy to jump into this story. At first, this felt very sweet and fluffy, which was fine for me. But then things get real, and emotional, and there's such an important message in the second half of the story, and I just loved it.

Jameson is awkward, and it's just adorable. He's tired of being a rambling mess and just wants to lose his virginity and basically get it over with, and hopes to find a perfect summer fling that will help him. Enter Will. Ahhhh, these two were just so freakin' CUTE. I just loved how Jameson would ramble, and then Will would call him cute or a nickname, and just how GOOD they were for each other. I love that they supported each other and had each others' backs.

Then, things start to get real when they find out that Will is working for Jameson's father. Will doesn't want to come between Jameson and his dad and Jameson doesn't want Will to not have the opportunity in a career he loves. I LOVE that they each care so much for the other, they put the other person first. And through Will, Jameson's dad becomes a more openly-loving parent, and Will finds a found family with Jameson's. I love how supportive and loving Jameson's dad is. I love the serious moment of Jameson explaining why he leaves his drivers license out. I loved Jameson standing up for Will to his family, and in turn that resulting in some healing for Will's family to begin.

I just LOVED these two together. So very sweet, cute, adorable. I loved their friends. I suspect we might get a story with Will's brother??? I can't wait for the next story in this series.
Profile Image for Denise H..
3,248 reviews271 followers
September 22, 2020
Exciting twists, hot sex, and deep emotions !

A unique M/M biracial tale with deep family undertones.
Blonde and blue-eyed, Will is scoring his dream job,

a PA for an exciting company. He broke away from the family business to follow what he’d wished for.
Will is a prize “date” in an auction for the LGBTQ community center, where shy Jameson, encouraged by his friends, bids on the beautiful man.
Jameson, is a nerdy, virgin and cute African American guy,

with a degree and heading into his doctorate in the fall. He’d like to get rid of his virginity this summer.
Jameson and Will have no idea that Will is the new PA for Jameson’s father.
Will finds Jameson adorable and they plan the date. They get to hang out, talk, eat, and make a deal for the summer, but they get so much more.
Later, when the truth comes to light about Will’s boss, our men are in deep, committed, and knocking on the door to love.



Neither man is willing to stop seeing the other, so they hide it for awhile, and the reveal is surprising.
I loved these characters, all the story’s elements and the passionate, extraordinary, sexy times.
We can see and understand how Will feels about his treatment by his own family, and the twist that hurt him so badly.
Jameson is by his side, comforting and loving.
A wonderful story that grips you, but has happiness, too.
ENJOY !

========
Profile Image for Andreas.
163 reviews42 followers
March 6, 2023
This book was surprising in so many ways. After reading the first book, I was set on reading the book about Danny, the friend of the protag couple. But that's just the third book and so I had to read the second one first. Which is about Will which wasn't really a favorite of mine in the first book.

But damn, this book made me love Will. I was pretty clear from the beginning that I would like Jameson. Introverted and awkward, it's just like looking into a mirror. But Will… he was kind of a superficial douchebag in the first book. But that was just the outside view. And well, a picture of him he himself had created and curated for years. This books shows a completely different picture of him.

But there were more pleasant surprises in this book. One of the biggest plusses is the lack of the usual third act drama. There's also no other real drama in this book, it's more like obstacles. That alone is worth an extra star from me.

Okay, there was a tiny bit of drama at the end of the book. But it wasn't between the main protagonists. It was also more of a sequel hook for the next book. And that was the next big surprise of this book. I really despised Jonathan at first. And knowing he's one of the two protagonists in the next book had me already dreading reading it. But then within just a single chapter the author managed to turn around the picture completely. Again. And now I can't wait to read the third book.

But there were also some quirks in this book that didn't sit well with me. Like the wording that sex is only when it's penetrative sex and everything else, like blowjobs and handjobs, isn't sex. Ugh.

Overall I really liked this book and enjoyed reading it. The absence of a third act drama and of all the other common drama tropes gets it a bonus star.

Now on to the third book, although I know the story of Jonathan will break me.
Profile Image for Agla.
840 reviews63 followers
February 23, 2022
I really enjoyed this one. The two MCs were fully fleshed out and very very cute. It was steamier than book 1 and that was good. The way they met was a bit ridiculous but why not. Jameson awkwardness was definitely cute and really liked Will as well. The way they supported and helped each other was great. It is an interracial couple and race was addressed in one chapter. It was done properly but I wish there had been more. Will (he is white) said that he would think about racial issues more because he had never noticed them which is good but that's not how it works I'm afraid. Becoming aware of white privilege in one situation is not enough. The pacing was a bit off to me . I would recommend this installment and I don't know whether Riley Hart has plans for more (can we get Daniel and Jonathan's story pretty please) but I would be here for it!
Profile Image for Ash&#x1f349;.
596 reviews113 followers
dnf
July 31, 2022
DNF @ 14%

I get the feeling this is gonna be cheesier than what I’m in the mood for now, I might get back to it in the future
Profile Image for Mir.
1,127 reviews64 followers
February 23, 2022
Yep. That’ll do 😍
Profile Image for Heather.
874 reviews6 followers
September 3, 2020
Ah! Jameson and Will’s book is going to make you feel the feels! What happens when a 22 year old virgin who gets painfully shy around any attractive man “buys” an overconfident man at a charity auction? Just the start of a sweet summer fling. I loved how Will helped Jameson realize the confidence was there all along. He made him realize his rambling was adorable to him, that he was into his big heart. In turn, Jameson turned Will into a bit of a marshmallow, toning down his overconfident brashness and making him realize he could feel. I loved how these two were so in tune and so present with each other. I loved when these two starting turning to each other, even with their great support of friends. Speaking of friends! I really enjoyed how they blended their friends so well. Jamison brought his two besties Kira and Ali who were a trip in themselves, and Will with his best friend Shaw and his boyfriend Elijah (who we met in Stupid Love). I also adored Jamison’s family and how Jamison and his father’s relationship strengthened throughout the book. There was a lot of obstacles thrown their way, because it can’t all be sexy experimentation. I love how they navigated those bumps along the way. Riley did another amazing job bringing this great story to us!
911 reviews21 followers
September 2, 2020
Oh this book!!! I just LOVED this book! Jameson was such a wonderful, sweet, adorable human being and Will-confident, self assured and cocky-was just the most caring and loving person when you peeled back his layers. Watching them stumble into love together was a joy. Right from the start there was a connection and I just adored how Will saw Jameson so differently from how Jameson saw himself. Over time Will helped Jameson feel comfortable being himself and become more confident...Jameson brought out the sweetest side of Will too!
There was so much more to this book than just the love developing between Will and Jameson. The family dynamics and relationships, on both sides, were so well done. I went through the gambit of emotions while reading--I laughed, I smiled, I felt fluttery, I cried, I gasped out loud and I sighed a happy sigh when it was all done. Riley Hart just writes fantastic books, and this was no exception, I just loved everything about it!
Profile Image for BevS.
2,854 reviews2 followers
June 12, 2021
Never thought I'd say this but I'm enjoying this series...and I'm happy about that. After reading so many of Riley's books years ago, I went through a slump with her [mainly too much sex and not enough story], she stopped being an autobuy and once an author leaves my orbit, it's sometimes difficult for them to find their way back onto my reading list...SO many authors to choose from 🤔.

Anyhoo, in this case, I loved Jameson and Will's story. Yes, it was more insta-love than I normally like, but it felt organic and real. Loved 'the professor's' family and his besties Kira and Ali, Shaw and Elijah from book 1 Stupid Love and already looking to book 3 Messy Love. 4.25 stars from me [didn't particularly like the cover I have to admit, wouldn't say he was hot 😏].

As far as Will's blood relatives are concerned, the least said the better BUT maybe Jonathan will surprise me by not making it all about him. Sometimes gay guys hate themselves so much cos of who they are [like Colin in Roan Parrish's Out of Nowhere] that it makes it extremely difficult to empathise with them as characters. They behave really badly towards any other gay characters i.e. bullying, violence etc., cos they're jealous of the life their braver brother/friend/relative has. Does it happen in RL? I guess so, it can't just be a fictional thing surely?
Profile Image for Stracia.
135 reviews
October 21, 2020
Nice Read

It was a nice book to read Jameson was cute and he fit well Will. Liked the character development I saw even though the book was a bit short, some real issues wete resolved. I wish Jay and Will the best muah xoxo
Profile Image for Leelah&#x1f341;♋️ Orion.
1,444 reviews56 followers
September 30, 2020
Thank you

First thank you for bringing another man of color to our lives. Thank you for bringing a brown person to our pages that wasn’t the stereotypical brown person. We come in all forms, awkward, smart, and nerdy being one of them. (I’m awkward smart and nerdy) I loved that this brown person came from a not broken financially stable family. I so enjoyed this. I enjoyed the journey of these to men. I loved watching them find their value in the world. Their value with love. The writing was amazing as usual, the smexy was hawt, and the side characters where great! I’m really enjoying this series. Please keep bringing brown main characters. While with it bringing our culture, our struggles and pain. Can’t wait to read the next book
Profile Image for Heather.
1,551 reviews9 followers
August 15, 2021
Awkward Love

Another Riley love. I struggled a little with this only because it’s hard for me to read so much awkward in a character so I kept taking breaks lol. Jameson was adorable but man, the poor guy! But It works out in the end for him!
Profile Image for Cassie.
316 reviews37 followers
October 10, 2021
Jameson... Oh my sweet sweet Jameson...

I must admit... I am a sucker for an MC that is that quiet, loveable, stammering "nerdy" type, that I feel like I don't get nearly enough of in male/male romances. Not NEARLY enough, to many beefcakes... but I can appreciate that too... lol. Anyways, I also love that Riley Hart gives us another story, with an African American MC and a bi-racial romance as well. We don't get nearly enough of that either.

I will also admit that I loved Awkward Love even more then I enjoyed Stupid Love. I had nothing but love and adoration for both Will and Jameson both throughout this whole book (unlike the hang-ups I had with Elijah at the beginning of Stupid Love... though Elijah does grow on me more in this book as well).

While this wasn't a true "slow burn" like some, and we get some love and sexy times from Will and "the Professor", I can also appreciate that we don't get everything from them until everything is fully discovered and the true commitment to each other is made for more then just a "Summer Fling". And while I'm not usually one for a slow build up... in this case it was well worth it. I also love how Jameson's stammering ways start to rub off on the all so smooth Will... SO cute. These two were absolute perfect together and so truly meant to be together.

Will secretly stands up for Jameson with how he feels towards his Father and helps to build up that relationship again and Jameson lays down the law and says how it is with Will's brothers and family one their mistreatment of him. I am soooo grateful that because there was such a build up and early slight "angst" between these two, that at the end when more is revealed about Will's family we don't get anymore unnecessary over dramatization and Will is able to see past it all and not hold anything against either party. He just loves one more and actually gets a better relationship with the other.

Also... Jameson' Father... absolutely hilarious... I cracked up when they were at the beach house... that was absolutely epically perfect.

*side note* I will say, that while I saw it coming.... I'm not a fan of the relationship between Jameson's two best friends... To me it just seemed unnecessary and kind of forced... In a... "oh won't this be cute if they are like a 4some together"... I don't know... I mean like I've said in other reviews I'm all for one discovering their sexuality and that it is ever changing... *sigh* it just didn't fit to me... It really was just kind of like Jameson is getting his happily ever after, so his two friends need it together as well even though there was no hit of this beforehand. *shrug* this is just me though.
Profile Image for Carol (§CoverLoverGirl§).
836 reviews75 followers
August 16, 2022
Awkward Love (Stumbling into Love Book 2) MM

This is Book 2 in a series of 3, I’d read 1 and then 3 for some reason. Each is a standalone but characters from Book 1 get their own book to tell their own relationship stories. I’ve had my favourite character in each book, Elijah, in Book 1, Will in Book 2, and Danny in Book 3. All have been excellent reads with different settings/backgrounds.

Will identifies as bi but prefers men. He works for a big Entertainment Company in Atlanta, Georgia. He loves his job as PA to the owner, Leon who is like a father figure to him. Shaw and Elijah are his best friends in Book 1. They asked him a favour to attend a charity auction to raise money for an LGBTIQA base in Atlanta.

Jameson is studying for his degree in Sociology and wants to become a Professor. He a dapper dresser, likes wearing bow ties, straw hats and braces . He’s mid twenties and still a virgin and wants to change that asap. His only experience is watching gay porn. Jameson has two besties, Kira and Ari who try to help him with his dilemma. They take him to an event being organised by friends, a Charity Auction, where dates with guys, can be had by the highest bidder.

I loved this story the best of the 3 in this series by Riley Hart who never fails to please with her writing. There’s no real angst as such but there are issues about coming out to family, being black and sibling rivalry.

I wish there were more in this series 😭
Profile Image for Jessica (Novel Confessions Book Blog).
515 reviews10 followers
May 29, 2022
A great read

This book had so much depth to. There was so much going on aside from just Jameson & Will going to experience buddies to an actual relationship. These men had complicated relationships with their families also, both in similar yet totally different ways. I loved how the strength of their personal relationship built them up to be better men and eventually they helped each other start fixing those complications with their families. So much depth I loved it so much. I definitely shed some tears in this book. The author is definitely a fave and will always be a one-click.
Profile Image for ML.
1,611 reviews1 follower
June 11, 2021
Awkward Love FTW

I got a new appreciation for Will. We met him in book 1 as Shaw’s friend. I fell in love with him in this book. Jameson and Will were SO endearing. This book made me smile so much. There were some tears too ngl.

Their perfect awkward love was just what I needed to read at this moment. The conflicts, the sweetness, so much sexy, made for such a beautiful story.

I’m glad we get more in this universe! Love this little slice of Atlanta. Off to read book 3…
Profile Image for Elithanathile.
1,927 reviews
October 5, 2020
Update:
What on earth is going on with this author’s characterization of our MCs and the storyline in general and all of that jazz?!? I think some of the people that she writes with are really starting to negatively impact her, because for one example, her endings are really starting to suck big time! Gone are her beautiful glorious wonderful HEAs and in their place she has spawned tentative HFNs like some OTHER authors ... !! I’m very surprised to say that I was bored out of my mind with this one and it just reads incredibly juvenile, and again I’m really disappointed in her apparent deterioration in terms of the writing in general but also her glorious wonderful spectacular HEAs that she is usually known for!! I don’t think that those specific wonderful writing traits that the author is usually known for are gone COMPLETELY, not at all whatsoever, it’s just very lacking HERE and I anticipate that it’s not going to pop up in future books or become a sporadic trend, though I’m confident it will not be!! May this be a hiccup that she completely rights herself from and just doesn’t happen again!! Some authors can hit a slump and it looks like these two books were it in regard and in comparison to her writing as a whole, so I look forward to it being isolated occurrences and that she’s back in full fantastic force in other and future books!!!




*******************************

I ADORE that this guy is wearing a bow-tie and that this book features a bow-tie wearing cutie 😊!!! Gahhhhhh bow-ties are DEFINITELY 🔥🔥🔥🔥🔥!!!

OHHHH and Jameson’s dad looks like Denzel Washington ... that man is just YUMMY with a RAWR 🔥🔥🔥🔥🔥🔥🔥🔥🔥🔥🔥🔥!!! Shame the cover-model couldn’t look more like Denzel too 😞!!!


Disclaimer:
Profile Image for SJ.
325 reviews4 followers
October 9, 2021
Seems mean to give this 2.5 stars so 3 it is. I didn’t vibe with this one!!!! I guess I wasn’t able to sympathize with Jameson’s anxieties like I was Elijah’s, but 1) his “awkwardness” was just…rambling? Being too chatty? Idk 2) the whole “I keep apologizing for being Like This and talking shit on myself omg I can’t believe you want to date me” thing is extremely unsexy and unromantic 2 me!!! It puts will in a spot where he’s just constantly having to talk Jameson down and reassure him that he’s fine. That’s not sexy date behavior! It’s not even charmingly weird date behavior! It’s just your annoying highschool friend who thinks saying cringingly mean things about themself is cool and self deprecating. 3) we don’t really ever get into why Will finds this behavior attractive? 4) every “reveal” in this is deflated into nothing. I don’t need a big contrived break up, but the initial setup promises something that the anticlimax ending decidedly doesn’t deliver 5) Will’s whole backstory is unfortunately identical to one of my favorite characters (Daniel in Roan Parrish’s “Middle of Somewhere”) but just…worse across the board. Daniel’s backstory is messy in a very realistic way, it impacts his actions and perceptions outside of immediate interactions with family members, and it’s intensely emotional not easily resolved. Will’s version of this is so comparatively milquetoast it pissed me off imao.
Profile Image for Corinne Colbert.
264 reviews4 followers
August 1, 2021
2.75 So I don’t think overall I’m a Riley Hart fan. The first person passive voice and the overall conversational tone bug me. Too many sentences start with the word “like,” which immediately makes the sentence a fragment. And I wish I knew how to do a word count search looking for the word “cute.” I think it was used 100 times, often more than once on a page. This a choice of the author and they have a lot of fans. I won’t be one. It gives me a headache.

It took me way too long to finish this, as in nearly two weeks. I even considered quitting, but I’m so far behind in the challenge I felt like I didn’t have the time to find another one, playing catch-up. I did enjoy the couple and the addressing of certain hot button social issues like racism, homophobia, and social anxiety. I feel like the loneliness each of the characters felt in their lives is realistically portrayed. The author also sets up the next romance in the series well. I’m sure it’ll be good for those who like angsty stories and I don’t see any other way that can go.
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