Sunday Morning Soliloquy - Musings of an Urbanite: Dating Follies by Leyla

Saturday, January 22, 2011

Dating Follies by Leyla

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Dating Follies by Leyla

It is late on a Friday night and I am not quite ready for bed. In the coming weeks, Sunday Morning Soliloquy will revert back to my "personal" blog and I will start a new blog to talk specifically about work-related events and learnings. This is a good thing because I truly miss just talking about myself and silly things.

I was thinking about all the ridiculous things that have happened to me on dates, so I thought I would go through some of them here.

The Guy Who Hasn't Been Into Me for a Decade

We all have that guy who calls every three months and says, "God, we need to get together soon for drinks" and never sets up a date. Well, I have a guy like that who has been calling for a decade.

I'm being very literal here, I met PJ in the late 90s, we met at a party and started to chat a bit. He asked if I wanted to leave the party and go to a secondary location. The secondary location was in close proximity to my apartment so I agreed. We had one drink at Le Colonial and I walked home (one block).

Our first "official" date was supposed to be a week later, but I had a photography class and I wasn't really that into him, so I was looking for an excuse. He wouldn't take "no" for an answer so I agreed to go out with him after my photography class got out at 9PM.

During the class, I received a text about a new lounge opening and decided to text PJ and tell him that I was sick and couldn't make it. Instead, I went to the new lounge with my friend Heather. About an hour into the night, I ran into PJ at the same lounge. I pretended not to see him.

Surprisingly, PJ asked me out a few more times but we never connected. I met someone else, dated him for two and a half years, PJ met someone else, moved to LA and got married.

Fast forward to two years ago. I noticed that PJ had moved back to Chicago but did my best to not run into him. Then one afternoon, in the parking garage of Whole Foods, our eyes met as I looked into the rear view mirror of BMW SUV. PJ got out of his BMW and walked over to my BMW blocking all the incoming traffic into the Whole Foods garage. Due to PJ insisting to talk to me, he ignored the traffic building in the garage for an inexcusable amount of time and I finally gave him my card.

BMW Z3 Roadster

This was one year ago. Since that time, PJ has called every couple of weeks and has tried to set up a date but has never closed the deal. He doesn't really want to go out with me, I think he just wants to stroke his own ego because I still take his call.

The Gay Donny

I met the Gay Donny around '00. I called him that because he looked like someone I know named Donny (who is already at the top end of metrosexual list), this guy was even more feminine, therefore we called him "The Gay Donny". But he was not really gay, I don't think.

The Gay Donny didn't like me either, I was never sure why he wasted his time. On our second date he confessed that all of his front teeth were caps. When I inquired about this, he said, "I used to be a terrible drug addict, I was on meth and I fell asleep and clenched my teeth to the point where my top four teeth crumbled." I'm not sure how someone on meth falls asleep either but I did not spend too much time thinking about it.

That was the end of The Gay Donny.

Jay, The Guy Who Sent Me Five Dozen Roses the Week After We Met

I know I am one to look a gift horse in the mouth, I really am, and you may be thinking I am a horrible person by this point. But think about it, who sends a girl five dozen white roses the week after they meet?

I met Jay around Christmas, we went on one date, maybe two. New Year's Eve was approaching and Jay was going on a ski trip. He felt bad that we couldn't spend the New Year together, I was indifferent because I barely knew him. On December 30th, my doorman phoned me and said I needed to get to the building ASAP because they couldn't accept a delivery of flowers. I was angry with my doorman because I didn't see what the big deal was...until I saw the flower delivery.

Jay had ordered five dozen roses from a flower farm in Central America. They were wholesale, long stem, white roses. You've likely never seen what a delivery of five dozen, long stem roses straight off the flower farm look like, so I will tell you - THEY ARE HUGE. The stems are almost four feet long and they arrived in large Federal Express boxes.

White Rose

It took me easily a half day to take the uncut roses (all with thorns) out of the boxes and tear the leaves off and cut them down to a size where they would fit into a vase. And then I had to giveaway at least 1/2 of the roses since I lived in a studio apartment.

I wish I could say that this was the only ODD thing Jay did but it wasn't. In fact, Jay did so many crazy things that I dated him for months for one reason and one reason only - I couldn't wait to see what insane thing he'd do next.

I could literally write a blog and dedicate it to Jay, that's how crazy it was dating him. He had an obscene addiction to Starbucks, he'd forget his wallet and we'd have to drive to his friends' homes so he could borrow money, he once lived in a hotel for six months, in his early 20s he had to declare bankruptcy for going into tremendous debt and his boss managed all of his finances, he had a severe Oedipus complex and he drove a Mazda Miata that he called "baby". It keeps going on and on and on.

I do wonder where Jay is today. We lost touch after my 29th birthday party.

Last summer, The Dude.

I will leave you with this disgusting picture. I met a guy who I will call "The Dude" because he was such a dude. We met on and he said he was 44 but I think he was really 47 (when I cyber-stalked him, I found an abandoned FB profile with a different age). This was the same summer I dated the 27 year old - so, technically, I dated a boomer and a Gen Y'er in the same summer...but that is another story.

The Dude lived in Wicker Park, he was an original from the early 90s who never married or moved on. He was still a big partier, he was pushing 50 and could not see that the opportunities in life that were available to him a decade ago were long since past. I felt sorry for The Dude because he was a nice guy but he was such a dude that I could not imagine him connecting with any woman.

On our third date, he asked if I wanted to meet at his place and have a drink and we could go to dinner from there. I agreed. He threw back three vodka sodas and then we went to dinner down the street. It was a perfect summer night, we finished dinner by 10pm, and The Dude asked if I wanted to go back to his loft and grab another drink on the rooftop deck. I thought it sounded like a good idea so I said, "Yes."

We arrive at The Dude's place and he immediately announces that he has to go to the bathroom. I thought the instant announcement was odd, but whatever. After he returned from the bathroom, we grabbed our drinks and headed up to the roof. He wanted to smoke a cigarette, so he lit one. About half way through his cigarette, he got a look on his face like he was a 6 year old boy in a panic. The Dude then announces "I've got to take a s**t" and quickly runs back downstairs.

I waited for The Dude to return from the facilities but headed home minutes later. The Dude and I didn't last more than two or three more dates. If you're a guy reading this and you're not entirely too sure what is wrong with the picture I painted above, perhaps you need to read The Relationship Handbook

A very surprised Adam


GoatKING said...


GoatKING said...


FeliciaCago said...

Ahahahahaha! More dating stories please, Leyla. Poor Dude and his pressing poop issues.

leyla said...

And, he used the word s**t - who says that to a girl while on a date?

Unknown said...

OMG...this is hilarious. Wish I had stories like that...hmmmm? Maybe I do.

James W said...

Very funny - I've got a good friend who has many similar stories. Some of the things are just crazy and I have to wonder is it her or are there that many "goofy" guys out there. I'm leaning toward the latter but....