High Fidelity: Anyone who has gone through a rough breakup knows how it can send you spiraling. Record-store owner Rob uses his latest breakup as inspiration to go back through his life and puzzle out what went wrong in his previous relationships and where his exes ended up. It's funny and unexpectedly touching.
The Remains of the Day: I never shut up about this book, but that's because it's brilliant and I love it. Anyways, this book, about the regrets you can't even admit to yourself, has as a major plot point a story of two people who might have loved each other and it will rip your heart out in a really lovely way.
Stardust: Catching a fallen star for your beloved seems really romantic, doesn't it? It's this fairy-tale-esque conceit that sets off the action in this sparkling Neil Gaiman story and it turns into an adventure story with some romance on the side.
Jitterbug Perfume: I love Tom Robbins, first of all. Second of all, your book club is going to need to be ready for some unabashedly adult talk. But if Alobar and Kudra can make it through hundreds of years together, there's hope for the rest of us, right?
Lolita: Sometimes the line between love and obsession is pretty shaky, like this literary classic about the "love" a grown man has for a preteen girl, Delores. He thinks he loves her, but does he or does he just want to possess her? It is definitely creepy, but it's just an incredible book.
Persuasion: Many of us have read the "major" Austen works: P&P, S&S, Emma. But this, her last completed novel, is a less straightforward love story. Anne Eliot listened to her family instead of her heart when she broke an engagement in her youth and never found herself another fiance. But when her ex comes back into her life unexpectedly, after she's all but given up hope of marriage, will the two find their way back to each other?
Bridget Jones's Diary: Speaking of Austen, there are some definite shout-outs to Pride &Prejudice in this hysterically funny book. That they made a great rom com out of it isn't surprising, but it loses the little touches like the notes Bridget keeps for herself about her weight and smoking so it's worth reading the original if you haven't yet!
The Rosie Project: I wasn't really expecting to enjoy this, I bought it because it went on sale for the Kindle and figured it would be worth a few bucks. But it's not as cliche as I thought it would be, and while it's not great literature, it's sweet and funny and a light, quick read. This could prompt a really interesting discussion about dating and mental health!
The Time Traveler's Wife: This is an off-kilter love story about a man, who experiences time jumps throughout his entire life, and the woman he loves, who doesn't. It sounds like something just dying to be considered "quirky", but it doesn't lose sight of the very real pain that could be created by this kind of thing. Very worth a read!
Dead Until Dark: Even readers who would consider paranormal romance outside their wheelhouse (like me, for example) should give the first book in this series, the basis for the True Blood TV show, a try. The first season of the show hews pretty close to the source material (this happens less and less as time went on), so there's already an introduction into this world out there. And if you like them, there's a whole series!