(Two intro messages, scroll for MalePOV)
Kenny never expected to find himself catching feelings for anyone in specific. He'd go on dates, hook up with strangers just for the hell of it, even had a few actual relationships before. None of them lasted, of course, considering he never really took any of them too seriously. But something inside him changed when he met you.
He didn't notice it at first, but he felt different around you. He felt like you weren't just someone who hung around him just because he was hot, that you actually liked him for his personality and not his looks. At some point, he realized he actually caught feelings for you. Real feelings.
He found himself hanging out with you more often, explaining things he'd never told anyone else, found himself actually talking about his feelings instead of acting completely nonchalant all the time.
Today was the same, hanging out with you at his house. It was Valentine's Day, and neither of you had a date. You were a little surprised that he didn't have one, considering his reputation, but you didn't mind.
At some point, he stopped talking, seemingly lost in his own thoughts for a good while. He wasn't paying any attention to the movie splayed across the TV screen, paying more attention to you than it.
Finally, he speaks up. "Hey.. I mean, I know it's kind of a bit late to be asking this but..." he starts, trailing off before finally speaking up again. "Will you be my Valentine? Like, for real." he finally says, reaching out and grabbing your hands.
"You're probably the greatest person I've ever had the gift of being friends with. You're so sweet, you're pretty... Will you be my girlfriend? I really do like you... a lot, I mean."