Dating Disaster Stories

Years before online dating services like Match and eHarmony were options, I placed a personal ad in the Penny Pincher.

The first woman that I went out with called and asked where I would take her. I said that she should pick a place.

Siobahn suggested a seafood restaurant. I liked seafood, so I didn’t mind.

During the meal, we engaged in conversation.

She was an au pair, someone who provides day care and light housekeeping while staying with a host family. The meal arrived. I had a nice salmon and she ordered lobster.

I thought when the check arrived, we would split it, but I kind of got the indication that au pairs didn’t get paid very much, so I shelled out the money and suggested that we walk across the street to a coffee shop for dessert.

She said that it was getting late and she had to be back to put the kids to bed. At that, she left.

I went across the street myself for cake and coffee.

I never heard from Siobhan again.

For my second date, Karen and I talked on the phone a few times. She lived in Rockland County and wanted to meet in a bar with a male friend as an escort.

Seeing how this was all kind of new to me too, it seemed fine.

I arrived early to the bar. I was dressed in slacks, a dress shirt and tie. Karen and Hank, dressed in leather and jeans, arrived a few minutes later; Hank sat at the end of the bar ordering shots.

Karen was a rather large woman with at least four visible tattoos. Hank had that “biker bar” vibe as he too was covered in tats.

Karen ordered a hamburger with a shot and a beer and wanted me to have a drink.

I got this nervous vibe that I was going to get rolled in the parking lot or wake up in a tub of ice without my kidneys, so I suggested that she and Hank enjoy a meal on me and I left.

The take-away? I left with all my organs and wallet. The only lingering question was who had more tattoos on them.

My last date from my personal ad was the most memorable.

We spoke on the phone and she asked if it was a problem that she was African-American. I said that I didn’t mind as my ad had all races and religions. She too lived in Rockland County and also was an au pair.

Kimberly asked me to meet her at a church. I thought it an unusual request, but figured why not.

I met her in the parking lot. Kimberly was this stunning, slender young woman. I thought we were going to walk to a restaurant nearby, but she invited me into the church auditorium instead.

There were chairs in a circle and coffee and cookies on a table.

The minister asked me to help myself. I sat next to Kim, and with that the minister began, welcoming everyone and asking if anyone would like to start.

Kimberly stood up and said, “Hi, my name is Kimberly and I’m a narcotic and alcoholic.”

Everyone clapped and welcomed Kimberly.

The minister then asked if anyone was new to the group and I stood, saying that my name was John and that I was here for the first time.

They asked me when I last used alcohol and I said about four months ago and they cheered. (I probably should have just sat back down, but I said that I wasn’t an alcoholic, which spawned a bevy of comments.)

After the meeting we walked to the foot of the Tappan Zee Bridge and sat on the rocks and talked. She was going to school for social work. I was a foster care caseworker.

It was actually kind of nice with the conversation, hot coffee and the lights glistening on the water.

At the end of the night she asked me if I could take care of her kitten because she was going out of town.

I said that I had a cat and wasn’t sure about introducing a new one.

She assured me that it was only for a day or two. My cat didn’t like the kitten and was hissing non-stop. The next morning, I called her to let her know that my cat was not having it and that she had to take her kitten back.

She gave me instructions to take the kitten to another woman’s farm somewhere in Rockland.

She took the kitten back and that was my last foray into personal ad dating.

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