Worst way you ruined a possible sure thing with a girl/boy?

Oof, yeah. I got this moment.

I had an old flame who was chatting it up with me, texting me out of nowhere when I put up a new profile picture on LifeInvader. She was getting flirty, I was getting flirty, things escalate... yadda yadda yadda, use your imagination. She drops the bomb of how horny she is, which naturally piques my interest. Suddenly, I remove my boner from the equation and start to think about the future and if this is really good for us in the long run to be doing this shit. It occurs to me that I've been with enough women. Is this really necessary? What if she gets attached? Is that really what I'm looking for?

So I stop her, and my next text is "I don't want this to get weird". Guess what happened next?

If you guessed "she loved /u/bladedhand for his concern over their relationship and mutual respect", you'd be dead wrong. But if you guessed "it got really awkward, she got self-conscious, and sex was never brought up again after that", you would be exactly right. I might as well have said "now think about your dad"; I turned her off instantly. For good. Good job, me. Always coming up with new and inventive ways to shoot myself in the foot.

That's the last time I look a gift horse in the mouth. That's the last time I take the advice of anyone who advises caution and care and -- ugh -- sensitivity going forward. Playing it hard and loose had always worked for me in the past; I deviated from that, and failed miserably. There's not a doubt in my mind that it would have gone in an excellent direction now that I think about it in retrospect, and I ruined it... by being a complete pussy. That was the soup that got away.

/r/AskMen Thread