Punch-Drunk Love
Even though I've seen this before and had a visceral reaction of admiration for it initially, I just forgot how tender it is. Maybe it's just because I'm not fifteen anymore and my view on relationships and just love in general has changed along with my self perception of myself but this while a harrowing view of isolation and anger, and what it causes someone to do from breaking down under it's weight, it's also one of the most romantic movies I can think of. Neither love interest is quite right, I guess you could put it that way, but that's what makes its special, it's just two people who understand eachother and accept the faults of what comes along with that. It's earnest while not being cliche or overly sentimental and that's why I connect with it so much.