Sipping Long Island Iced Tea in Front of a Brick Wall

An Awkward Date at The Comedy Cellar in 1989

Back when I was in college in 1989 I took a date out to a show at The Comedy Cellar on Macdougal Street.

I was introduced to that comedy club at an early age when I was about 14 or 15 or so in the 1980s when stand-up comedy was booming. Went back to the club a few times afterwards, but not much. This time I wanted to do something different for a date and showing her The Comedy Cellar seemed like a cool alternative to mindlessly hanging out at some bar in the Village after going to record stores.

Anyway, she was like like 19 or 20 years old or something. She didn’t go to college with me, but I met her on campus during registration. She scored a summer job working in the registration office, she was cute and I asked her out.

So we headed to The Comedy Cellar and we were carded right away at the door. I could legally drink, but she genuinely looked like a kid. So they kept an eye on us from the second we sat down.

The place had a two drink minimum, so I ordered a Long Island Iced Tea and let her have a sip. The second the straw hit her lips some matronly owner/manager came over and whisper-shouted, “If she takes one more sip out of your glass you’ve both kicked out! Got it?” So we spent the rest of the next hour or so terrified and wondering how to make the most out of the rest of the evening.