Ok, Cupid, I’ll Give It a Try

Let’s talk about dating – a topic that I have managed to avoid on the blog so far.  It’s probably related to the fact that I am barely dating at all.  But I have tried (a little) and have come to the conclusion that there are no normal, single men in Chicago.  None!

I did have a crush on someone quite a while back, but of course that went nowhere because he was kind of dating (and later officially dating) someone else.  I made it very clear I was interested.  This means, I told everyone in my office that I had a crush on him, and we would all giggle when his name came up in conversation.  Isn’t that what normal 28 year olds do?  Wait, only 7th grade girls?  Damn.  I’m totally out of moves.

Since I wasn’t meeting many single guys on my own, I turned to online dating.  A part of me finds sites like OkCupid and Match.com absolutely terrifying, but I felt like I didn’t have much choice.  I did peruse OkCupid for a short time when I was living in Mississippi.  Almost every profile I read professed a deep love of ‘huntin’ and ‘muddin’, and although I love a pick up truck as much as the next girl, I felt that the available pool of men were not really for me.


Fast forward to last fall.  I updated my OkCupid location and started window shopping for a boyfriend. I was actually excited.  I was reading profiles of guys who liked art and theater and other creative pursuits.  They had interesting movie and music preferences and were able to sound witty and charming in their profile – I think an online dating profile is the most difficult medium a writer can tackle.  And only a handful mentioned killing animals for fun!  I was so, very optimistic.

It took me only a few dates to become as jaded and cynical as everyone else.  Here’s why:

Guy # 1:   We planned to meet for drinks, but the time kept getting pushed back because of his other plans.  By the time we met, it was 11 p.m.  (I had literally lived in Chicago for only a few weeks at this point, and I was more than a little nervous about setting out by myself so late.)  I texted a few friends to let them know I was going on a blind date, and what this guy’s profile name was in case I disappeared suddenly.  (I have done this on all subsequent dates.  If I go missing, I want to make sure the police will have a good lead – DUH!)

Conversation with this guy was going ok UNTIL the guy asked me if I did any improv

ME:  No, I prefer working on full length plays.

HIM:  Well, you will. This is Chicago.

Excuse me, but please don’t tell me what I will or won’t like.  Once the improv door was open, he admitted that he had a sketch comedy show with some his of friends all about their experiences with online dating.  We started talking about the bad dates he had gone on (I, of course, had none to speak of since this was my first ‘online’ date ever).  If you are ever on a first date and this subject comes up, CHANGE THE SUBJECT IMMEDIATELY.  I promise, you will learn nothing but horrifying things about this other person.  The date was so-so, but the guy kinda went a little cuckoo when I told him texted him that I wasn’t interested in a second date.  He sent a few more dramatic texts saying I should have told him I didn’t find him attractive instead of saying I might be up for a second date.  Kind of a drama queen.  I can’t help but wonder if our date has made it into his sketch show.

Guy #2:  We met for drinks.  We had plans, then he cancelled the plans because ‘a friend of his was really bummed and needed him’ only to text me an hour later asking if I was still up for meeting.  Those sketchy circumstances aside, I actually had a good time.  Conversation wasn’t awkward (the drinks helped) and the guy seemed to be pretty normal.  Attractive, funny, and he seemed to like me.  There was even a goodnight kiss involved.  Then, I experienced the fade away.  He just disappeared, never to text or message again.   (You should follow the link to a very funny dating blog called Stupid Cupid.  These ladies are hilarious and understand the pitfalls of OKcupid)  If you’re keeping score, I’m 0 for 2.

Guy #3:  This time I met the guy for dinner.  We messaged a few times before our date and realized that we lived on the same street.  He literally lived four houses down from my apartment building.  I almost cancelled when I found this out.  What if it was absolutely terrible and I kept running into him in the neighborhood?!?  But I got over that anxiety and went anyway.

The date wasn’t so bad, and it really helped that this guy was tall and very cute.  He was a little strange, but his good looks were making up for it.  The strangest part of the evening was when he admitted to taking classes at Second City NOT because he was interested in improv but to improve his social skills.  (huh?)  Then, he wanted to play improv games at the dinner table.  (I actually agreed to attempt this with him.  In case you couldn’t guess, the game was a disaster.)  That WAS the strangest part UNTIL…

When the meal was over, Guy 3 reaches in his pocket and says, “I brought something for the occasion.”  I was petrified.  What is in his pocket?  Why is he making sudden movements?  Is this guy the OKcupid killer?  Then, he pulled out a Chat Pack.  What’s a Chat Pack, you say?

It is a deck of conversation starters.  Ideal for car trips and classroom activities.  Here are a few sample questions from the manufacturer:

* If you could have any book instantly memorized cover to cover, which book would you choose?
* Of all the movie characters you have seen, which one do you believe is most like you?
* Which of the 12 months do you think would best describe your personality?

Basically, this guy needed a cheat sheet to have a conversation.  I was so relieved that nothing illegal came out of his pocket, I agreed to ‘chat pack’ conversation.  It wasn’t SO bad, but the conversation had been going fine!  Why did we need help?

I actually ended up going out with this guy a few more times (did I mention that he was really tall and good looking and lived just down the street?).  But of course, we had hardly anything in common and he was just as strange on later dates (but without the chat pack).  I haven’t seen him in months because he moved to go to medical school.

After these and few other OKC dates, I swore it off for a while.  I kept logging on and looking at profiles, but I didn’t actually want to read any of them.  It was so much work.  Not to mention, it was a little depressing signing on to receive boring, disgusting or no messages at all.  So, I took a break.

Until recently… please stay tuned for part 2 of online dating adventures.

2 responses

  1. Pingback: Ok, Cupid, Where are you hiding the normal guys? | Leaving the Land of Cotton

  2. Sorry this is so wildly belated but just wanted to say thanks so much for giving our blog a shout out! We love your blog, too. I basically died when you brought up the ‘chat pack’… I’ve gone out with wayyyy too many guys who legitimately needed one of those to carry on a conversation. Keep the hilarious hijinks coming! –the ladies of Stupid Cupid

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