Category Archives: Dating Disasters

One Investment Banker’s Approach to Dating

In New York, dating is an activity. Nay, it is a sport. And in this sport, there are many crazy sequences of events that lead to many hilarious stories (some of which end up right here on this blog). Once … Continue reading

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10 Worst Pick Up Lines

The following pickup lines are not the typical come-ons you find on those cheesy lists of pickup lines that nobody actually uses. These are the ones that guys have actually used in real life situations in efforts to hook up … Continue reading

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Flashback: 1990′s Dating Disaster- Shacking at the Waffle House

Now, this will date me a little, but I am not ashamed! Approximately 13 years ago while a University student in South Carolina, a girlfriend of mine, let’s call her “Susie,” experienced the most unbelievable set of circumstances after a … Continue reading

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Flavor of the Day

I met this guy at a party with mutual friends one holiday weekend and exchanged numbers after fun, flirtatious conversation and shared interests. He seemed like a really cool, international guy. After that night he would text me every few … Continue reading

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Missing the Target

I got set up with a guy through a mutual friend (always a risky situation) but we were going to go on a double date so I felt a little bit better about it. The four of us wound up … Continue reading

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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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