She posted a meme about being single, so I made a dumb flirty one back using her pic (nothing bad, just funny — something like a cheesy meme caption about “the one who got away”). I thought I was being clever and subtle — playful enough to get a laugh, but also just flirty enough to drop a hint that I was into her. I even spent a few minutes tweaking the font and making sure it looked casual, like I just threw it together. Honestly, I was feeling pretty proud of it. But somehow, in a moment of pure idiocy, I clicked the wrong name in my messages and sent it to my boss instead of her. I didn’t even notice until hours later when I got a reply notification during a meeting. The worst part? He responded with, “Not bad. But she’s way out of your league.” I just stared at my screen for a solid minute, completely frozen. I don’t know what’s more embarrassing — the fact that I messed up so badly and involved my boss, or the creeping suspicion that he might actually be right. Now every time I see him at work, I can’t tell if he’s silently judging me, secretly amused, or just patiently waiting for my next disaster.
TL;DR: Tried to flirt with a girl via meme, accidentally sent it to my boss instead. He roasted me. Now I live in shame.
Comments
Idk if you wrote the name of your coworker in the texts, but if you didn’t, it seems quite obvious for the team that you are very close to her
The fact your boss would say something like that is troubling. Is he the “alpha” type trying to assert dominance by belittling those he sees beneath him? I understand the method of humor, but it’s not like it’s a close friend poking… it’s a person in a supervisor position, deliberately making a demeaning comment.
Seriously, don’t pay any mind to the response. It’ll be forgotten by all before you forget it. And don’t let it influence your self worth either. There will always be people out there trying to minimize your accomplishments and people that will try to lower your self worth.
You do you, ignore the comments of others as you never know who wants you to fail and who wants you to succeed. Surround yourself with people who genuinely celebrate your successes and who are there to pick you up when you are down.
This is AI slop. No-one spends minutes adjusting the font for an image macro trying to make it look like they didn’t (and I say that as a guy who puts too much effort into making it look look like I put no effort into my hair). Also typical AI phrasing like, “The worst part?” “silently judging,” the em dashes, etc.