June 30, 2007

Butt Plug

Last Monday, I went on a date with a random girl that I didn't know at all.

When we set up the date, she said she wanted to go to a specific bar because they had dollar drafts. That should have been a sign. I suggust getting dinner first and pick a small thai place near the bar.

When I show up at the restaurant, I discover that it is apparantly closed on Mondays. Thankfully this does not bother the girl. We merely just walk down the street to another Thai restaurant, as there is a Thai restaurant roughly every other building in Lakeview.

After we order, she launches into a long story about her roommate. Apparantly the roommate had spent the other night attempting to get guys' attention by loudly talking about all her sex toys, specifically her butt plug. My logic was, if that was annoying/strange to you then, how would the story not be the same to me?

That type of attitude was typical of the entire date. It was difficult to read her signals, as she seemed to mix them up with stories of other people.

I don't think there is a lot of potential here. She hasn't graduated college, despite being old enough to. She hasn't even picked out her major yet. Nor did she really strike me as that intelligent, which is a quality usually held by women who interest me. Also, I am not sure if she is physically attractive. She was definetly bigger then most of the girls I date, but I don't think she is fat in any way. Big boobs can be fun, right?

Long Week

It has been a long week, very active.

The highlights include:
Monday - date
Thursday -Sushi Lunch
Friday - Friends' Wedding

I'll post about each of them seperately.

June 26, 2007

Goodbye Friend

Went on a date last night, it was strange. I'll write about it later, however, something else is bothering me right now.

For some reason, my cable has been out the past couple days. I now only get the basic four and the public access stuff.

It is like in grade school when your best friend went to summer camp.

My New Hero

I have a new hero.

As I got on the red line this morning, I let the girl waiting with me on first. She took the last open seat, right by the door. I was fine with this and was glad to take the end of the el car, where you could lean against the door. After stimulating my brain with all the RedEye had to offer, I glanced up. I noticed that the girl was staring very intently at her copy of the RedEye and I could see her ears focusing on her iPod. Then I saw why. The guy next to her, my new hero. He was probably in his thirties, though it was hard to tell. The combover wasn’t very good, but what hair he had was wavy, even his chest hair. I don’t think sitting was best for him, as it made it appear that he had a bigger gut then needed. He was probably about 5 foot 4, I would guess. But the face definitely had character.

Anyways, he was running his best game to this girl. I applaud his efforts. Picking up a girl on the el is hard, especially when she pretends she can’t hear you over her iPod. Some men, myself included, would probably stop then. But not my hero. He continued to try to strike up a conversation till Belmont. At this point, I thought my hero had given up. But no, he pulled a brilliant maneuver. Instead of engaging her actively, he changed it up. He pretended to fall asleep and lean into her, creating physical contact. It was an amazing move, the girl never saw it coming. She had to weaken her defenses and push him off. I see now where I have so often made the mistake, I never realized the inactive yin to the active yang. I have learned from a master today.

With this opening, he actually got the young professional to talk to him briefly. I think some comments were made regarding what the next stop was and whatever was in the RedEye. And then she shut down again. Once more, I would have quit then, but I am not a master. My hero, nay, he is now OUR Hero, then pulled a maneuver so complex, I think I almost strained a muscle watching it. He channeled his best club beats and started going with the music. I’ve seen it down in clubs and concerts where everyone can hear the music, but here, it was all him. He became her new iPod. Somehow, she continued to focus on the RedEye. It was at this time he turned and I saw the master stroke. To demonstrate his cavalier attitude, he had chosen to ride the el this morning with a cleverly placed bit of napkin about the size of a grain of rice on his face.

By this time, we were at Grand, and more people were getting off then getting on. Our Hero could hear the clock ticking. Once again, he zigged when I would have zagged. A novice, such as myself, would have foolishly continued to put all my eggs in the basket I had been working on for 8 stops. Our Hero instead stands up, leaves her (wanting more, I assure you), and bravely asks a blonde wearing sunglasses underground (I can only assume so no one catches her staring at our Hero, nothing else makes sense) for the time. After which, he turns to place himself in between the two women, who clearly must hate each other with competition and announces, “My stop is next.” A brilliant move which puts the pressure on the girls. They are now the ones with a time limit. Our Hero expires in one stop. Once you hit Lake, he is gone.

The blonde gets so flustered, she can only go take a seat. I am sure she intended to get back up and give our Hero her number, her body, her self, whatever he wanted.

But she was too slow, the stop came. Our Hero and the first girl got off and I can only assume have now started their long happy life together. She was so excited she was practically running down the el station. Almost too fast, he could barely keep up.

I have a new hero, and I took notes.

June 24, 2007

On the Red Line

I, like many thousands of young professionals, college students, and homeless bums, take the red line between work and home. Not only is cheap, runs often, and drops me off a block from work, but there are also a lot of people to watch. Sometimes they are fun to look at because they are really strange, and sometimes because they are hot girls. Usually, I just sit, watch, listen to my I-pod and read my book.

The other day on my way home from work, I was caught in the 5 o'clock rush. I was stuck in the area right in front of the door. More people continued to pile in every stop. Before we got above ground, a really attractive girl got on and began standing by me. I checked her out. However, it was clearly way too crowded to attempt to begin a conversation. Eventually, we hit stops where people actually get off and the el started to clear. A seat opened up and she went to it. I followed and struck up a conversation. I found out that she was new to the city and was downtown job hunting. I gave her my business card with my cell number on the back and got off at the next stop.

This was very strange for me because I have never really hit on a girl. I have always just fallen ass backwards into relationships. Usually girlfriends were friends of friends or involved in some club with me or something along those lines. I have never asked a girl for her number at a bar or anything like that. Likewise, I don't think I have ever gone on a date with someone that I did not date since high school dances. Just dating around wasn't what I did. It is something that I am learning now.

She called about four days later and we are going out to dinner after her little sister leaves town.

June 23, 2007

Went To A Gay Party

One of my friends from high school works at a summer camp in upstate New York. Before he left, his boyfriend threw him a going away party. His boyfriend is a lawyer at a fairly large firm in the city. Therefore, there were going to be a lot of lawyers at the party.

I hate lawyers.

I told my friend that I would only go if I could pretend not be a lawyer. I just didn't want to deal with the whole lawyer-lawyer talk where you pull out your legal penis and measure. After some brainstorming, I decide to be a architect. I know enough about it to speak convincingly for a party conversation. Plus, they are lawyers, they will be drunk. That makes lots of things easier.

I get to the party, and as suspected, it is all lawyers and homosexual males. Two groups that I have no desire to date. I get the tour from my friend, meet the boyfriend, and do some catching up. I talk to a couple of lawyers, they buy my story. I talk to some other people, they buy it. All is going good.

Then I am talking to an out of town couple. I tell them about when my friend came out of the closet. Which prompts the question, "When did you come out?"

"Ummm... I am straight."

"oh"

It amused me.

Later, another guy from our high school shows up. My friend let him know that I was pretending to be an architect. He decides he is going to help me, which is nice. Sadly, he is very drunk. That leads to this exchange when I am talking to one of the few non-attorney females.

He staggers up, obviously drunk and drools, "Hey Mr. Architect, I want you to build me a house."

"I told you, I rehab old industrial buildings to make them more green friendly."

"But I want a house, you need to design it."

"I don't do that, I can recommend you to someone. Right now, let me introduce you to Beth." (making up the girl's name, i forget).

Not taking the hint that he needs to stop saying architect, "But you are an architect, right? I want you to architect."

Worse wingman ever.

June 22, 2007

Sushi Girl

This is up to date posting, as it is currently happening. It probably would be funnier if I posted some other stories first, for compare and contrast purposes. I will have to get them up later.

Regardless, two days ago I was slightly behind at work. So I decided to do a working lunch. I went across the street to a little cafe that makes decent sushi. A roll is a great working lunch food. If you know how to use chopsticks, it is easy to eat, not messy, and allows you to do other things while eating.

So as I walk in, I hold the door open for the lady behind me, as I tend to do (I am one polite motherfucker). I notice that she and a couple other ladies in the cafe are well dressed professional type ladies. I always approve of that look.

I approach the counter, order my spicy tuna to go and give them my name. I then take a seat at the counter, waiting for my food. One of the ladies grabs her coffee and gives me a smile on the way out. I always appreciate that, I look good in biz casual clothes, so the girls should approve. After a couple minutes, I get my food and go back to work.

The next day, I am looking at Craigslist's missed connections because otherwise I would get work accomplished. I notice a posting for Spicy Tuna. I open it thinking I will get a good restaurant recommendation from it. It says, "*The Guy*: I like spicy tuna, too. Maybe we could eat lunch together?"

Eh?

So a couple e-mails to Life Coach later, I reply asking where the sushi comes from. The reply is correct. I e-mail a couple more questions, all answered correctly. I get a picture, I kinda remember her, she's not fat.

As a result, I am going on a lunch date sometime next week with some thirty year women who watched me order raw fish.

June 21, 2007

Pop Culture

Yesterday, Life Coach and myself went to see "Knocked Up". Also, this past weekend I read "The Average American Male".

Both the book and the movie had some parts that were clearly meant to be satire on modern American dating, especially for young men. Satire generally is accomplished by going over the top a little bit. However, in both of them, i have personally done stuff above and beyond the satire.

I am ahead of the curve.
Fuck.

My Life Coach

At one point in my debacle I started talking to an old friend.

Actually, she was a girl a dated for about a year in undergrad. We had stopped talking, mainly because LTR was very jealous of any contacts i had with old girlfriends. However, this relationship was one of those ones where you are better friends then significant others. Now, I tell her everything. She has become my Life Coach.

The dynamic is amusing because Life Coach isn't too good at relationships either. So hopefully we can learn from each other's mistakes. Or at least laugh at them.

I think it is good to have someone that you can admit to all the crazy/stupid/fucked up stuff you do. Everyone does stuff they shouldn't. Especially me. If I wasn't able to tell anyone... I would go crazy.

Thanks Life Coach.

June 18, 2007

You have to have rules

I figure there are two types of attraction: physical and mental. Now, I am all about the mental. I have to find a girl funny, interesting, able to hold my attention (and I may have ADD, so that is a challenge). However, first impressions are based solely on looks. I figure I deserve it all, therefore there is a rule.

RULE No. 1:
Don't date ugly chicks.

June 17, 2007

Background

I am a 26 year old single man in Chicago. I currently live by myself. I work downtown as a lawyer. I am tall, good looking, funny, smart, etc. Honestly, I am a catch. However, I am horrible at dating.

For nearly four years I was dating the girl I thought I would marry (hereinafter (told you I was a lawyer) called "LTR"). However, after one really unhappy summer, I broke up with her last fall. One month later, I tried to get her back... by proposing marriage. That debacle was about 3.5 months of pure hell for me. Eventually LTR broke my heart and I was forced to move on. Sadly, thoughts of her still affect me to this day.

More importantly, after being with LTR for so long, I have no clue how to date. Dating in your mid-20s is apparantly different then dating in college. I failed to recieve the memo. Therefore, I am writing this to help others. Or to at least give others some laughs.

Enjoy