Jack The Matchmaker- My Own Dating Service

When I was a newlywed I had quite a number of friends who were still single, both male and female. I was 27 and still enjoyed nights out with the boys. There were a number of nights in which we closed down the establishments we were hanging out at.

The advantage to going out with the guys that way was that I had no interest in trying to meet anyone. There was no pressure of trying to find a way to introduce myself to a woman. I didn’t have to worry about pickup lines being viewed as stupid, lame, awkward or silly. I didn’t have to try and pretend to be anyone or anything other than simple old Jack.

The beauty of this was that when the boys would point out their interest in one of the ladies I could walk right up and say anything to her. And I do mean anything because there is almost nothing that I won’t say. I can be downright fearless.

Often I would walk up to the woman and the two or three friends she was with and just start talking. Sometimes I would begin by telling her that my friend in the blue shirt thought that she was incredibly beautiful and that he was too shy to introduce himself. Normally she would thank me for the compliment and she would ask a few questions about him.

This led to numerous dates for my buddies. Had I not been married I could have done pretty well for myself because more often than not one of the other girls would strike up a conversation with me.

What surprised me about this was that some of them would look at my wedding band and practically throw themselves at me. It made me wonder if I looked more attractive because I was off limits or if there was something else going on. And every now and then one of them would try and lecture me about how it was wrong for me to talk to single women as a married man. I had a lot of responding to those comments. Give me an opening for some silly banter and I’ll be happy to oblige you.

There are some good stories that I could share, but I think that some people might try to break my arms if I shared them, so I’ll have to see what I can offer. In the meantime, here is a short story about a silly trick that the boys and I used when I was single.

There were times when we would approach a group of women and ask them if they would help us solve a bet, win a competition or some such variant. Usually it was presented as “my friends and I have a bet about which one of you is the best kisser and I wondered if I could kiss you and find out.”

Cheesy, horrific, terrible line, but it worked like a charm. It was amazing how many times the girls would agree to this. But again, those stories are probably best left untold.

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