Dating Blunders Volume One

It’s Valentine’s Week so that means that it is time to tell stories of love won and lost. Or in my case, I’ve decided to use this week to write about some of my worst dating experiences ever. Oh and I will tell the story of my first date with Kim on Thursday as it will tie in nicely and at least that one will not rank as one of my worst experiences ever. I have more than enough of those to go around.


Now before I tell some of my stories I have to remind people that in the not too recent past I used this very blog to openly promote myself as a date for Valentine’s Day. In fact, I had a standing offer in Kansas City to take any woman who volunteered to be my date on Valentine’s Day to the following: 1) Dinner at the Outback Steakhouse (value up to $25, everything above $25 directly ordered by said date must be paid separately. Shared appetizers will be split evenly but please bear in mind that I have a strong dislike of Bloomin Onions because there are some things that even deep drying does not improve, 2) Tickets to see Air Supply in concert at the Harrah’s Casino and 3) one cocktail of their choice at the Casino venue and let me say as someone who had a lot of $6 beers at that damn Voodoo Lounge in that place that is a very nice addition to the package. No one ever took me up on the offer but one of the girls on a competing team did say that she would have but she had to be out of town that day. Seriously, I would have done it just because the sheer thought of seeing Air Supply on Valentine’s Day with a random person would be too good to pass up.

Things were so backwards in Kansas City that I did actually utilize the It’s Just Lunch dating service. Of the many things I learned from that experience number one is that I shouldn’t choose dating services based solely on their advertising in every in flight magazine that I have ever seen. I went on fourteen or fifteen dates in the year or so I was a part of it and I saw a grand total of one woman on a second date. And there was another that gave me her number but never returned my calls. So yeah, not a great history there. However, my final date using them has to be the worst blind date that I have ever been on, made worse by the fact that I technically paid for the experience.

It was either January or February and it was the only time the restaurant where the date was set up to be was within walking distance of my apartment. Given that I lived in the nightlife / entertainment district of the town this never made any sense to me but oh well, at least this time I could trudge through the snow to get there. I sit down, starving for dinner, order a beer and wait fifteen minutes for this woman to appear. When she finally does you can tell that she really doesn’t want to be here either.

I was always surprised at how game people were on these blind dates. I mean, it was an entirely contrived experience, this meeting of a random stranger that someone told you about over the phone for dinner on a Tuesday night. And some nights after a crappy day of work the last thing you want to do is sit down across from someone and make small talk. I always tried and for the most part I always at least had an interesting conversation. Besides I can always talk about books or music or pop culture and find some common point of interest. This night however there was nothing we had in common.

She wasn’t in to music while I was going to concerts every week. She was into hiking whereas I felt that if God wanted us to climb mountains he would have made them smaller and installed hand rails for safety purposes. The crowning moment came when she mentioned that she was originally from Washington and I sensibly asked if she gets the opportunity to get back home and visit her family much. To which she let me know that both of her parents had passed away.

I believe the awkward pause that hung in the air after that statement is still going on.

Trust me, there is nothing you can say in that circumstance that can make you feel like you’ve recovered even though this was a subject that I had no idea about and quickly apologized and switched topics. It is just this feeling of being the biggest ass in the world. We both decided quickly that we didn’t feel like ordering dinner (even though I was absolutely starving) and I walked her to her car and let her know I was walking home. I watched her drive away and then quickly walked one block over to my favorite bar where the bartenders were pouring a beer for me the second I walked in the door. To be honest, for those five years in Kansas City Harry’s was as much of a home for me as my apartment and that night, after sitting through the most awkward conversation that I had ever had, the only person I wanted to talk to was a bartender.