Well this is a failure/bomb/cockblock/dating disaster/etc. for the record books.
I managed to screw up a date by
USING INCORRECT PRONOUNS.
So I go out with this girl and it's going real great, she's laughing at my jokes and we're having fun and it's going real well. She's a fun girl, big on social issues (lesbian, transgender, sexual minority group politics, etc.) and she really feels strongly. Cool, I respect that, I agree with her on several stances.
Later on we meet up with some friends. One of them is a guy wearing a dress. Cool, I'm down, I shake hands and learn all their names. Everyone's getting along.
So the conversation goes on, we're all making jokes, and dress guy makes a joke to my date. She sort of makes a silly face and goes "Huh? I don't get it." And I go "Haha, I think he meant (expands on the joke a bit)."
Suddenly it goes stone cold silent. She just starts glaring at me. The conversation dies off. I don't quite understand, but the group kind of dissipates.
My date is now still cold and distant, a far cry from the flirty girl 30 mins earlier.
So soon she says she has to go and she goes home grumpy. I still don't quite get it.
I check my messages, and a friend who was in the group is texting me.
Shady1:dude
Shady1:dude
Shady1:wtf
jax_ice:yo what's going on, Sheila totally
Shady1

ude what the fuck were you thinking
jax_ice:ditched me
jax_ice:me?? what did I do
jax_ice:she was totally hkappy an hour ago now she left angry
jax_ice:after we saw you guys
Shady1:holy fuck dude
Shady1:you screwed up
Shady1:you called her a he
jax_ice:what?????
Shady1:you don't use male pronouns fopr transgender people
jax_ice:what did I do wrong
Shady1:you said he
Shady1:Sheila introduced you to her as a she
Shady1:man you know how she really takes that seriously
jax_ice:...
jax_ice:ah fuck
Shady1:yeah man you screwd up
Shady1:sorry man your not getting laid tonight
jax_ice:ewfawtgaerh
So the lesson here is that if your date is really big on social issues and uses extremely specific pronouns,
1. Don't assume it's a crossdresser
2. MAKE SURE YOU PAY ATTENTION AND KEEP NOTES AS TO WHICH ONES TO USE or else you'll be going home and playing Assassin's Creed 3 to work off the frustration.