My Very First Internet Date

Well, they always say, start with some practice dates when you haven’t been out there in a while. This was exactly what I decided to do.

I started talking to a guy on match.com. On paper, he seemed like a great catch. The only thing that stood out to me was that he was 42 years old and had a roommate. Living alone for the past 12 years, I thought it was strange that anyone would put up with that in their 40’s. However, everything else seemed to fall in line.

He lived in the ‘burbs (can be tricky as a city girl) and wanted to come downtown for dinner. He asked me which restaurant has a parking lot next to it.

Um, have you been to Chicago? No such thing. valet perhaps but no parking lot.

He decided on a place called Jack Sullivan’s because 3 years ago he met a friend there and found parking out front. Fine by me.

I approach him at the table, and he seemed like a nice clean-cut guy. We sat right by the window.

I was a little rusty at this dating thing so there were a couple of pregnant pauses at the beginning.

As we were talking, I see him continually looking out the window. As I can’t stand when someone is distracted that way, I asked what was wrong. He said his car was parked out front and he wanted to be sure no one was bumping it while parallel parking. I wondered what kind of car he had but assured him it was fine.

I then learn he does not have two nickels to rub together. He has a hard time finding his rent money which because he has a roommate, was $300.00/month.

His career was scattered to say the least and had a hard time keeping a job. He was one of those schleprock type guys where everything bad happens to him.

For example, he decided he wanted to do a cruise for his 40th birthday. He couldn’t find a friend to go with (also concerning) so he went alone. He arrives on the cruise and learns it is a spring break cruise and he gets sea sick.

He spent the whole time with his head over the toilet while 21 year old girls told him how ancient he was. See what I mean?

I realize I had about enough and decided it was time to end the date. He offers me a ride home. I said, don’t worry about it, I am fine to jump in a cab. He said, no, I insist. I wasn’t getting out of this so I finally gave in.

It then occurred to me, I will finally see this car that he has been so worried about all night. We walk up to it and it is a blue Buick Century with the hood ornament up front. I couldn’t believe it, this is what he was worried about? It wasn’t a vintage car either, it was a tore up, old car.

I get in the car with him and I see this orange light illuminated on his face. Well, of course, that was the service engine light that was permanently on. We then take a couple of turns and I see this pair of older lady sunglasses on the dash board that kept sliding around as we drove. I then thought about it, I bet this isn’t even his car?

He had to borrow it from Grandma for the date?

He drops me off and we never went out again.

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Lesson Learned? Practice dates are important as you don’t want your first date in awhile to be with someone you really like. Get the nervousness out elsewhere.