A bartender in Portland told me his worst date ever lasted 11 hours, and now I finally feel better about my 90 minute disaster

Alice Smith · 2026-09-30T10:30:03.606908+00:00

I was venting to him last Friday about a date where the guy showed up 40 minutes late and then ordered for me without asking. He laughed and said he once got stuck on an 11 hour first date because she kept saying "just one more place" and he was too polite to bail. I could not believe someone had it worse than me, so we spent the next hour trading stories with two other people at the bar. It made me want to hear more, what is the longest or weirdest date you have ever been stuck on and how did you finally get out of it?

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A bartender in Portland told me his worst date ever lasted 11 hours, and now I finally feel better about my 90 minute disaster | Awkward Date Stories - Opinions Matter