You really go balls to the wall eh
Here's one I can share.
Awhile back I started seeing this young lady who was very into group encounters, namely of the female ratio being higher than the male ratio type. One night she texted me very bluntly looking for company for a very specific activity. Unfortunately I had 2 20 page papers due two days from then (damn grad school) so I informed her I couldn't swing that night but I would have tons of time the next week. We agreed to postpone our core strengthening exercises until then.
Fast forward a week to Thursday night went I went out with friends to 80's night (ie cheap beer and cheap pool). One of these friends was another young lady I had been seeing for awhile who was also interested in ladies. We had discussed the possibility of a certain thing happening often but never found a friend.
After about 8 or 9 PBR pounders I recall this fact and inform my friend that my current companion enjoys female company. My friend enthusiastically agrees and I proceed to text the chick I'm seeing "I think I found us a third". Thirty minutes pass, which to my drunken self feels like 3 hours so I text "Oh not appealing to you anymore eh?"
At this point it's last call so my friend (different friend) and I walk back to our apartments and get home about an hour after leaving. At this point I remember my romantic companion's query from the previous week and text her "I'll see you tomorrow night" (but in far more specific and blunter terms).
The next morning I wake up and check my phone to see if I got any texts and spy the ones I had sent the previous night. At this point I realize I mad a grievous error.
A few weeks prior to this my friend surprised me by visiting from Korea. During his stay he was using his dad's cell phone, I never added him to my contacts so the texts just came up as the phone number in my phone. Well I also didn't add my current romantic partner's number to my contacts, instead just texting her phone number. In my drunken state I sent all of those texts to my friend's dad (who is quite homophobic and had thought for many years that my friend and I were both bi). Sadly my friend saved my number in his dad's phone so he knew exactly who they came from.
That is one of the very few times in my life I've been embarrassed.