Relationships.  They are so hard.  I have a few loved ones going through some rough times with relationships, and it’s reminded me of all the evil men I’ve loved before, and some that I didn’t love at ALL but I continued to date for whatever reason.

My worst blind date was set up by my friend Sheila in Chicago. I haven’t seen Sheila in more than ten years, so I doubt we need to protect her anonymity. She set me up with a guy that worked in her company’s graphic design department. He was part-time there, and the rest of the time he worked in a record store on Michigan Avenue. I walked down to meet him for our afternoon date wearing khaki shorts, an orange tank top and clogs. (Do not question my fashion sense – that detracts from the story – but the outfit is important to the plot.)

The plan was to go to an art museum downtown then go to dinner.  After that, we’d see. 

Dating Lesson One:  Do not allow the first date to be open-ended.  This guarantees you will be stuck with a loser for upwards of six hours.

The art museum was closed for renovation, so we decided to go to his house so he could change out of his record store uniform (you think??) and go to dinner.  It turned out that he lived with a one-eyed cat, a stripper and a guy who was smoking the world’s tallest water bong when I walked in the door.  The guy with the bong was eating a huge plate of ground beef.  My date was pissed that the roommate was doing either the smoking or the eating of the beef without him.  I sat down on the couch to wait for him while he changed, and that’s when the stripper walked out dressed for work.  The one-eyed cat sidled up next to me. He smelled like Mary Jane. My date asked me if I minded if he smoked. I thought he meant cigarettes. I was wrong. After he’d puffed a few, he put his head in my lap and told me his therapist said he was ready for a relationship again.

I don’t know why I didn’t run screaming at this point. Probably because I wasn’t even exactly sure where I was. This guy lived about five neighborhoods south from my Lakeview apartment.  We went to an Indian restaurant. He ordered the fish. I ordered vegetables, being a vegetarian at the time.  When his fish arrived, it looked a little like Don Knox.  My date was so completely freaked by his food making eye contact that he proceeded to a) eat all of my food and b) tell me he was out of cash.  I paid for our meal.

We went back to his apartment and picked up two of his friends.  The male friend was wearing a leather dog collar. The female friend had immigrated from somewhere in Asia and spent about ten minutes telling me she had a tattoo of the goldfinch, the state bird of Iowa, on her ass.  We went to a club downtown called Drink. It’s a club, with beautiful people and really expensive drinks and house music.  Let’s recall two facts about this story:  1) my date had no money and 2) I was wearing khaki shorts, an orange tank top and clogs.  I did actually run screaming at this point, but in order to get home (I was out of money after buying him and his friends two drinks each), I had to let him give me a ride. He’d grown up on the north side and gave me a guided tour of his old neighborhood and elementary school. I had him drop me off in front of an apartment building that wasn’t mine, walked home, and called Sheila, threatening to kill her if she ever set me up again.

Dating is rough. I feel for you girls out there.