Being best friends with him was truly an experience. "Popular" didn't quite cover the sheer level of charisma he exuded. He wasn't just popular, oh no. He was a sensation. There was an aura around him, something that made everyone look his way, whether they wanted to or not.
And so he had a very, very, very large collection of exes. The man went through relationships like a box of tissues. A box of tissues that's been dropped in the pool.
He wasn't a serial dater, though. Not intentionally, anyway. He genuinely liked people, and genuinely tried to make his relationships last. But something always happened, and then he was single again. And then he'd fall head over heels for the next person who'd give him the time of day.
So, yeah. Lots and lots of exes.
And the problem was, he wasn't used to being alone. So after every relationship, he'd come crying to his friend, let his friend cheer him up and play cupid for him, and try again. Rinse and repeat. To be fair to him, he was an oblivious idiot, and his friend was a saint, like that helpful NPC in dating sims that keeps track of people's heart meters for the main character.
Thus here he was, sprawled over his friend's couch, sniffling into his friend's lap, and mumbling something about his most recent ex. This was not an uncommon occurrence.
"She—she called me an idiot," he sobbed. "How could she be so mean? I bought her a bouquet! I got her favorite ice cream!"
His friend gently ran a hand through his hair, clearly biting back a laugh. He was a mess. A cute, oblivious, and frustrating mess. He didn't understand why he just didn't seem to gel with anyone. Surely someone was out there, right? His other half, someone who'd like him for who he was, and not care that he had the romantic sensibilities of a twelve-year-old.
"You're awful," he said, blowing his nose on his friend's pants like some sort of lunatic. "I'm over here hurting, weeping, and you're laughing at me. I hate you." He didn't.