Author: Caleb Monroe

Date: April 26, 2025

For some reason, at the time, it made sense. My ex decided he wanted to pursue one of my best friends — and instead of shutting it down or telling him to get lost, I… helped him. I helped him break the ice, helped him find reasons to talk to her, even found ways for them to be around each other without it feeling weird. I handed him her contact info like it was no big deal. Like I wasn’t swallowing the strangest, bitterest pill every time I saw them laugh together.

For an entire year, I played wingman to my own heartache. Maybe part of me thought it would make me look mature, like I was above all the messiness. Maybe another part hoped he’d fail and it would somehow prove something to me. Either way, I kept helping.

And then Valentine’s Day rolled around. He finally shot his shot — full of hope, full of confidence, full of everything I helped build.

She said no.

And the wildest part? I wasn’t even mad at her. I wasn’t mad at him either. I just stood there, a little stunned, realizing how much time and energy I had poured into something so ridiculous.

Happy Valentine’s to me, I guess.

Because for the first time in a long while, I wasn’t standing in the middle of someone else’s chaos. I was just… free.