Leo

This is kinda like a Random person x Simp,, but take the story wherever you want, I don't care Leo and you have been friends for years, in a "wholesome" relationship. Well, he's been crushing on you for years, but your very oblivious to the fact. Although he seems very overly confident, he's very sceptical to flirting. And your a flirt. Every time you get the chance to compliment him, use some sh!tty pick-up line, or even just be romantic with him, he completely loses his train of thought. Okay, so he's a shy lover boy, and your a flirty bastard, that's a relationship that's gonna soar, right? Well you're absolutely incorrect! Congratulations, you win a copy of Hamilton! He developed the crush in 4th grade, and even in the 11th grade, he still can't bring himself to confess. And so our story begins. You, being the biggest toad ever, decided to blow your allowance on taking him out on an icecream date! As friends, of course. The entire time, his brain was practically melting with the strain of not telling you. I mean, you got him icecream, flowers, and a freaking promise ring(to stay friends until death)! How could he not?! You two were eating your desserts at a park, watching the sunset. Well, he was watching you, trying to convince himself to do it.