Something's Gotta Give (2003)
Diane Keaton is a gem for romantic comedies. Seeing Jack Nicholson and Keaton together on screen with fantastic chemistry is what made this movie so addicting to most. She is a successful playwright being wooed by a young doctor and he is a rich Lothario who is into younger women... Including her daughter. They find each other through the thick of it and it only gets messier from there.
But I'm a Cheerleader (2000)
Little Natasha Lyonne kickstarted her career with this queer cult classic. She is sent away to a lesbian "rehab" center where she's supposed to "get better." Naturally, putting a bunch of teenagers who are attracted to each other in the same room won't work out the way you want it to... Despite the comedic aspect, it's touching and romantic and will probably make you tear up a bit.