I actually disliked this less than expected given all the other reviews and stuff I've read about this.
I do think that Hopeless Romantic has a great setup and handles many important topics that are not common in the genre, but the way some things were handled and the combination of it all wasn't great.
My main issue with this book was Nick, the protagonist. He's impossible. I can't even 100% describe what about him bothered me so much, but the way he behaved, what he said and his thoughts frequently made me speechless and extremely uncomfortable - all of that things that occured way before he learns that Katie, the love interest, is trans, and the subsequent mess.
Hopeless Romantic has several main topics:
One is that Nick falls in love with Katie, who is trans, which Nick knows very little about. He makes a lot of mistakes, saying and thinking things that hurt and misgender her. He also talks a lot with her and she corrects and calls him out a lot. Does Nick learn a lot? Yes, definitely. Does he always learn gracefuly? ... not really? He accepts what she says immediately and doesn't repeat mistakes directly, but somehow his "oh yeah sorry, I know" reactions felt a bit like he was brushing her off. I cannot tell if it was meant that way deliberately, but that was how it felt to me.
I do think that books about characters who are still learning about what it means to be trans and be with a trans person have their place, and can be very important - but in this specific case it felt like a wrong decision for the book.
Another big topic is that Nick realizes he's bisexual, when he identified as gay his entire life. The discovering bisexuality plotline isn't exactly new, but I have never read it from the perspective of someone who previously IDed as homosexual instead of hetero.
On it's own, that storyline I think is handled rather well. There are important conversations about bisexuality itself, and the whole "gay man falls for a woman" is handled very sensitively.
But.
Big but.
I find that storyline combined with how Nick treats Katie after she tells him she's trans.... not good.
Let me elaborate: The two of them meet by chance and after a while end up spending a long day together where they have a lots of fun. The entire day, Nick is very attracted to Katie, and very confused about why he is attracted to her given that she is a woman and he's a gay man. Later, as they talk, Katie brings up her being a trans woman - having assumed that Nick knew she was trans, which Nick hadn't. At no point previous to that does he even question her being cis (though I guess there are "hints" dropped for the reader - her voice cracks, she is pointed out to be tall, her hands are big but soft... which is a bit questionable in itself, but made worse by how awkward and unnatural the writing is at parts, especially when it comes to describing the characters). So when she tells him she's a trans woman.... Nick's first feeling is relief. Because "that explains why he, as a gay man, is attracted to her". Katie immediately calls him out on how wrong that kind of thinking is - that he is implying she is not really a woman - but.... god. It's just so uncomfortable. And combined with Nick having previously established himself as a huge asshole I really wasn't feeling it.
While talking about Nick being an asshole: Nick has a roommate, Tucker, who is a-spec (another minor thread is about Nick and Tucker's friendship). At some point Nick talks to his friends about Tucker, mentioning he might be asexual, to which his friends reply with "Ew". Nick replies with "Not ew, just different" and.... that's it. No further comments or thoughts are spared to this interaction that left me entirely speechless.
Nick's friends in general made me really uncomfortable, not just because one of them is a bigot and horrible in so many ways, but also how that makes Nick behave.
While Nick learns a lot over the course over the book, the first 20 % are really hard, and the improvements only really take place after the 50% mark. I understand why so many people DNF'ed this, and to be honest, the only reason I didn't DNF was because I was bored at work.
Even as the book improves, some things still made me side-eye it.
I greatly appreciated that at no point Katie is put in danger for being trans - there are no direct confrontations where she is involved. But there are direct confrontations between Nick and other people about her. Which felt weird: Nick defending her, telling people Katie's genitals or how he has sex with her are non of their business, and what he says in those scenes in itself is good, but it was weird that there were so many conversations explicitly ABOUT Katie with third parties, yet she wasn't there for any of them.
So.... there's some of my thoughts about this mess. I'm sure I forgot to mention many things, and there's many reviews out there by more relevant voices abotu this than mine.
Ultimately I didn't dislike this book as much as I thought I would, I like the topics that it handles, but I'm not convinced by the execution, and Nick is just plain the wrong character for a story like this in my optinion.