Did I accidentally offend him with my crappy flirting?

[Anonymous]

So there's this guy I have a huge crush on. I know it sounds like middle school, but he's really out of my leauge, but also I really like him. We've known each other since like, birth, and he's just gotten cuter as we get older. We'll, I found an old childhood pic and sent it to him. He basically said it was awesome, and I had the *brilliant* idea to be like "Right? Back in our prime lol" but like I meant that sarcastically. He texted back something along the lines of "LOL that's right," so I'm hoping he took it how I meant it, but guys, would you be offended by that?

[MementoMori777]

nah i think you chillin, dont overthink so hard lol

[Asker]

Haha thank you. I'm working on it 🤣

[MementoMori777]

fair enough 😂

[WanderingLoveWizard]

Yeah you fucked up. Time to move on

[Asker]

Ahhh, I feel so bad. If he'd gotten the vibe behind it, he'd have appreciated it. But he's one of the last people I'd want to hurt.

[WanderingLoveWizard]

Lol, I was being sarcastic. Don't worry about it darlin

[WanderingLoveWizard]

Just cut past the bullshit and tell him he's hot. Seriously

[Asker]

AHHHHH, the problem with text 🤣

[WanderingLoveWizard]

Lol, yes it is. My fault, not yours. People can't tell when I'm kidding

[Asker]

I'm thinking about it. We've got 20 something years of being pals, even if we weren't close riding on it though. He still looks out for me when he can. And heck, to be totally honest, we haven't talked about relationships in awhile. I'm fairly confident he's not in one, but that'd be a crappy way to find out. I don't know. I'm thinking about it.

[WanderingLoveWizard]

Well as a good friend, there's nothing wrong with you asking, "So, is there a special girl in your life?"

If he says no, you can say, "Oh really... 😍"

[berisky23]

I wouldn't worry and just tell him how you feel. It sounds like a pretty good ice breaker to me

[Asker]

So I thought it'd be a good ice breaker too, then I got in my head, then despite knowing exactly how he'd reply, I have no idea what to say now lol.

[berisky23]

Ah yeah I feel you! It's cool just carry on with it, tell him what you like about him, or ask him what your eyes are saying to him😉

[slatyb]

Just ask him out. He's not out of your league.