Category Archives: Dating Disasters

Boo! I’m your date, and I’m an asshole.

I met a guy downtown one Saturday night and was excited to learn we’d both gone to college in Boston. It was a fun scene with good music, so we chatted. When I’d decided it was late and time for … Continue reading

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1 Tequila, 2 Tequila, 3 Tequila…

A few weeks ago, I went on my first Match.com date. We met for drinks at a Mexican restaurant and started with some Margaritas. Everything was going alright and rather normally. I began to suspect my date had been drinking … Continue reading

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How’s your health?

A friend of mine set me up with his coworker, and I should have been skeptical for a few reasons, but as a single New York woman quickly approaching 30, I was working on keeping an open mind. Here were … Continue reading

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The Modern Prince Charming

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Cats or Dogs?

                       I had hooked up with this significantly older man a couple of times and was somewhat interested in him. The second time we hooked up we took the opportunity to go out to brunch together and get to know … Continue reading

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3rd Date Dilemma

So I went on two dates with a guy, and the first two had gone reasonably well so I agreed to a third. At the end of the date, the guy asked me back to his place for ’after-dinner drinks.’ I accepted … Continue reading

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Slightly Out of Range, A Flash in the Pan

I created an online dating profile back in January and said I was interested in men ages 27-35. One of the first normal-seeming guys to hit me up listed his age as 36…slightly out of range, but I thought “Why … Continue reading

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The Hit and Run

There was this guy that had liked me for a while and we had made out a few times and then he moved away. I knew he had recently come back into the city, and one night he called me … Continue reading

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Do you want to skip dessert and get high?

As a middle-aged divorcee in the ’burbs, I can attest that the dating opportunities cup does not runneth over. That said, recently, I was introduced to this guy via a friend while at a bar listening to music. We had a … Continue reading

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Prepare to laugh. This is an EPIC voicemail that was left on the wrong guy’s machine from a

Prepare to laugh. This is an EPIC voicemail that was left on the wrong guy’s machine from a girl named Dominic (huh?) who either works at Ebay or Jamba juice and loves the name Eunice but doesn’t know how to spell … Continue reading

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