Four Dates in Four Days

Not only did I run my second half-marathon in a month this weekend, I embarked on a dating marathon: four dates, four days, four dudes, four duds.

I already wrote about Date One and how it turned out to be a pleasant, friendship oriented experience.

Date Two was far more interesting. Jill, Kristin, and I went up to Indianapolis on Friday night and stayed in a hotel because we had to get up so early to run the half. Jill and I had gentleman callers in Indy so we decided to double date and carboload at the same time. Kristin embraced her role as the judge of our dates and a Party of Five was formed. Every other person in Indianapolis wanted to carboload as well, so it was impossible to get a reservation at an Italian restaurant. As Jill and I were trying to coordinate our dates, we managed to get in at a Mexican place. Our feelings of anxious anticipation were mounting as we arrived at the restaurant but this soon gave way to ridiculousness when we got seated at a round booth in the corner that was on a raised, curtained platform. It was the most bizarre table in the entire restaurant – a cross between a VIP area in a club and the interior of a genie bottle. Jill’s guy showed up first. We had low expectations for him because of a creepy drawing that he drew of Jill’s face after their first date, but he seemed relatively normal. And by relative, I mean relative to my date who was extremely awkward during dinner. Prior to the double date + one, I thought that he was a normal guy with a sense of humor. In this group setting, however, he decided to bust out really lame jokes (sample: Did you hear that Disney is coming out with a new line of exercise videos? Yeah, the first one is Pilates of the Caribbean) and stupid stories about wearing a sandwich board as an undergrad and getting randomly beat up at Denny’s. It was completely cringeworthy, but fun in a it’s so bad it’s good way. But in Battle of the Dates, Creepy Drawing Guy pulled off a surprise victory!

Date Three was actually my second date with Over Thirty Guy. This was the most traditional and best date of the four. We had dinner and spirited conversation and everything went really well. However, I’m not sure if our “values” jive. I have no idea what my values are, but I know that I feel unsettled when people contradict my standards of manners, outlook on childrearing, political views, and financial situation. The first two violations are challenges that might turn into dealbreakers while the latter are challenges that might turn into personal growth opportunities. I’m getting a bit less concerned about political compatibility in my dating partners because I live in freaking Indiana and no one thinks about things the way I do. The financial thing is a new one, though. I am a poor grad student and I have mainly dated other poor, but eventually upwardly mobile type people. There are times, like every time I look at my checking account balance, that I half-jokingly, half absolutely want a quote-unquote Sugar Daddy. And by sugar daddy, I mean a guy who at least has a job! But what I have come to realize about myself is that I am actually deeply suspicious of wealthy people. I look more closely at their morality than I do other people; I look for them to prove that they are not materialistic and superficial money-grubbing soulless miscreants. While there is something attractive about someone who is successful and established, there is also something unattractive and intimidating. If he already has all of that, where is the fun in building a life and accumulating things and success together? And in the same way that wealthy men wonder if women are just attracted to them for their money, I am the type of woman who wonders if men with money are just attracted to women for the power trip. Money is absolutely one of the most crucial aspects of a relationship and a lot of it has to do with power dynamics. Dating a fellow indigent sucks because you need money to do things, but dating a man with money feels kind of dirty. I think I could over that, though. I wouldn’t say that I am fair about many things when it comes to dating, but money is one of the last things that I care about. If the dynamic works and he’s a good guy, I don’t really care if he is a prince or a pauper. As for Over Thirty Guy, he seems really nice and generous, but I really don’t know him well enough yet.

Date Four: By this point, I have dating fatigue. I have used all of my good date stories, expended all of my dating bubbliness, and asked all of the good questions. My capacity to be delightful was significantly diminished. Luckily, it was a super casual lunch thing and I coasted through it. The date itself was very bland, but I’m not sure if it was because I didn’t have much left to give or because he is just dull. Regardless, I don’t think there is enough chemistry there to warrant further exploration. I need someone who is lively and opinionated and tells stories. Relationships are like great comedy duos – you need the timing, the chemistry, the ability to feed off of each other. I have had too many dates of feeling like the solo entertainer playing for an audience of one.

In the end, it was fun to sprint through so many dates back to back, but I don’t think I will do that again for awhile. It’s exhausting. Plus, if one bad date can make you feel bad, it is incredibly defeating to have four in a row go wrong.

And the search for Mr. Biscotti goes on…