Chicago Single Life

I want a life lover that will go that far

nospam@example.com (Ryan) — Thu, 28 Jan 2010 08:44:08 -0800

On Sunday I went out with this woman named Roberta. I bet a lot of your are thinking wow that is not a very attractive name and if I told you I was setting you up on a blind date with a woman named Roberta you would be like no way man. Well the opposite couldn't be more true. She is one of the most beautiful woman I have ever seen in my life, let along actually gone out with on a date. She is 34 and she is a translator. She is fluent in 6 different languages so she gets a lot of work doing translation for high end clients like law firms, politicians, and the entertainment industry. I know I said in my previous post that I was going to try and think of something creative to do for a date vs the regular take a girl out to a restaurant date but sorry I failed on that one and we ended up at a restaurant afterall.

I took her to this place called Zealous Restaurant which is one of my favorites. It is fine dining and they really do things up amazing there. She seemed unimpressed by the place so I guess she has been to lots of fancy places before. I know she makes good money for the work that she does. We had a very interesting conversation over dinner and things didn't seem to relaxed. She talked a lot about her job, well because I was asking her lots of questions about herself and what she did. I spent some time talking about my job etc but I didn't get into too much detail because divorce is not the bets topic on a first date. The food was excellent as usual and so was the service.

We left that restaurant around 9pm and headed over to this place called 955 Fulton Lounge so that we could just chill on a couch and I could put my arm around her and sip a cocktail and listen to some cool chilled lounge music. That is exactly what happened and it was a really cool vibe and cool place. We chilled there until about midnight and then we left in a taxi to go to her place. She invited me up and so I up I went. We were both standing in front of her liquor cabinet and she asked me what I wanted? I replied "you" and then touched her face with my hand and kissed her passionately. She tasted so good it was amazing and she smelled really good too and so did her place. We made out on the couch a bit and then eventually I left and called a taxi and rode the way home with a big grin.

Red is my favorite color

nospam@example.com (Ryan) — Sat, 23 Jan 2010 06:47:31 -0800

Hi everyone, sorry it has taken so long since my last post but like I said I have been busy as hell over the last couple weeks. My caseload is so high that I am considering hiring an assistant. The firm has offered before to get me an assistant but I am trying really hard to make partner and I don't want them to see me using the assistant as a crutch. I want them to know how hard of a worker I am and that I don't need to rely on other people to get my job done.

Let me tell you about how things are going with the redhead search. I have heard back from 5 of the original 7 redheads I messaged a few weeks ago and this morning I combed through the online dating site and I found a few more potential redheads so I sent them off messages, we will see how that goes.

Out of the 5 redheads, only 3 of them are natural redheads but one of the ones that isn't is soooooooo hot I am not sure I care anymore about the redhead thing. She is so hot though I bet she is getting messages from tons of guys and I am sure I am up against a lot of stiff competition. I have been so busy with work I have not been sending messages back and forth with these girls as often as I think I should be. I don't want them to lose interest or to meet some other guy they like better because so far all 3 of them seem to like me.

I am talking to all 3 of them on msn and I know they all are anxious to meet me and now that I have some more free time on my hands I am going to setup some dates with them but I want to try and think of something unique and creative vs just taking them out to a restaurant or a bar or a lounge. I am going to spend some time today googling date ideas etc and I will let you know what I come up with.

A new year, and a new strategy

nospam@example.com (Ryan) — Tue, 05 Jan 2010 09:35:06 -0800

Happy New Year all. I hope you all had a great holiday and I hope you all made some new years resolutions. I personally made a resolution to make sure that I am targeting the right kind of girls this time around. With that being said, I decided not to talk to that girl Rachel anymore. She is just too confusing and last week I was reading that relationships should be simple. Also I decided that I want to date a redhead.

This morning I searched through the online dating site and I messaged 7 different redheads. I am not sure if they are all real redheads or if some of them have dyed their hair. I only want to date the girls who have real red hair. It is too hard to tell if they dyed their hair because girls can dye their eyebrows as well then it gets really hard to tell.

These redheads that I messaged are a wide variety of ages. Some of them are in their early twenties, some of them are in their late twenties and some of them are in their thirties. I even messaged one woman who is 41 but she looks really hot. I expect to get some messages coming in pretty soon from these women.

I really hate the holidays because whenever I get back to work after them I am always backlogged and then I get a whole bunch of new cases. This happens because a lot of people will decide to get a divorce in the early part of the new year. They do this because during xmas and shit they don't want to upset their children so they agree to wait until after the holidays so their kids can still enjoy one last time together. Also lots of people create new years resolutions and getting a divorce is a common one. I will update more as the new messages come in and I have something interesting to report.

A chilled out chilly Thursday

nospam@example.com (Ryan) — Sun, 13 Dec 2009 08:53:33 -0800

On Thursday I took that girl Rachel to a little eatery called Lou Mitchell's Restaurant. The place is really average but the atmosphere is great and so are the staff that work there. I frequent the place at least once a week. You might be wondering why me the fancy pancy lawyer with all the money and power is eating at such a small hole in the wall type of place? Well first off I used to go there all the time with my father when I was younger. Secondly it is a good place to take a girl to see if she is a gold digger. I can usually tell right as we pull up in front of the place whether or not the girl approves or not of the joint. I have had women say "We are eating here?" and I have replied no and drove away to another better restaurant then once we are seated I will say I am going to the bathroom and then never come back and just leave them sitting there hanging, alone, uncomfortable, wondering what is going on. I usually get either an angry or a confused phone message or email the next day and I usually just never respond. I think that it is a shame that so many women are brought up to leech off of men. Just because they see that I make money, they think that I am a dummy and I want to just shower them with gifts and generosity. This couldn't be farther from the truth. This place is my restaurant test. So anyways Rachel passed the test because when we pulled up out front she said oh this place looks cool I have never been here before. This shows me that she is open minded and also won't easily jump to conclusions and inaccurate assumptions. It was only 6pm so the place was just slowly starting to fill up from everyone getting off of work etc. We had some coffee and ordered dinner and we talked about a lot of different stuff. It was a weird dynamic though because I did not feel a lot of sexual chemistry between us, it was more like just two friends talking getting to know each other. I am not sure why there was this lack of chemistry but it was there. Maybe because she was just shy and didn't want to let on that she liked me, or maybe it was because I was kind of in a bad mood before the date and didn't really want to even go so I was all poo paa about the whole thing. Maybe it was because I'm not sure if I want a real relationship so I was holding back. After we finished eating we went for a walk in a nearby park and watched some dogs play with each other. It was pretty cold though so eventually we got back in the car and I drove her home. We exchanged a brief kiss out front of her place but nothing special. I am kind of confused about this girl and I am not sure if I want to see her again. I think I have some stuff I need to work out.

OMG Persian girls rock my socks

nospam@example.com (Ryan) — Tue, 08 Dec 2009 16:36:39 -0800

So after my date with Rachel I let some time pass and then I eventually called her. She was wondering why I had taken so long to call her and that her girlfriends were telling her that I was some kind of player because I was following these so called player rules where the guy will wait X number of days before calling the girl in an attempt to play some kind of control. Ok so they were right? What was I going to say? I decided to lie and tell her that my grandmother had passed away on Sunday and my Mom and Dad were both devastated and because of course they are divorced and don't live together I had to spend double the amount of time consoling both of them traveling to both of their houses. I told her I just wasn't in the right mindset to call her and that I was jet lagged and barely slept most of the week. She bought it all of course. So because our date was so dry in the chemistry department I felt that it was important for me to ask her some touch questions about how she felt towards me. It was time for me to qualify her or disqualify her as I prefer to look at it. I asked her if she thought I was attractive... there was a big pause so I reworded it to do you think I am handsome? She said yes I was cute. Cute? Why is this girl holding back? I told her I thought she was really attractive and that I was had to restrain myself from coming on strong to her and asked her how she felt about that. She just giggled and then I knew things were good. I got off the phone with her but not before securing another date with her for this coming Thursday night. Yeah that's right, she is not worth spending my weekend time with.

So what DID I do last weekend you ask? I'm sure you all can't wait to hear what kind of exotic women I spent my time with and what foreign perfume scents I basked in this weekend... muahhahahhaa. Her name was Farina and she was Persian. I started talking to her last Wednesday and arranged to meet her on Saturday night at this lounge I like called Funky Buddha Lounge. I had only seen a picture of her face online and the picture was kind of shitty. I never even talked to her on the phone before I met her. I got there before her and was waiting in a chill booth not ready for what to expect. I usually make it a practice to see a picture of the girls from head to toe. I don't want any fatties. No one likes fatties. So I am all chilled there buzzing and noticed I got a text message from my bro Nathan so I was replying to his text, looking down at my Blackberry when all of a sudden she is standing in front of the table. I nearly jizzed in my pants... Olive colored skin, dark pointy eyebrows, big natural tits, and curving thighs and ass - one of the hottest women I have ever seen in my life. I got up and she kissed me on the cheek. We sat down and the waiter appeared. What followed next was quite lawl. I was so dumbfounded by her beauty that I couldn't think straight and I just said "Beer, whatever you have on tap" wtf bbq sauce was that - is this a movie? Who does that? So of course she says well we have blah blah blah and blah - I don't really drink beer too much so I was like well which one tastes like Stella? She said none of them so I like well do you have Stella in a bottle and she was like of course so I was like ok I will have a vodka 7up. He was like ooooooooooo kay buddy. She laughed and I think she thought it was a joke but I never actually meant to do any of it on purpose. So we talked a bit about our work and about our favorite things, likes and dislikes, no one asked any awkward questions about past relationships, we kept things light. We talked about movies and about family and she said she had a really big family and that they all lived locally. Finally the food came and we ate it... I was pretty hungry at that point. After dinner we had coffee and cake and that was fun. She said she wouldn't mind hitting up a club or something and well I would like nothing more than to see this fine creature move her ass on the dance floor. So we went over to a place called Enclave Night Club and had some more drinks and danced a bit. By around midnight she was kinda buzzed and was giving me the fuck me eyes and I was like w00t. So we GTFO that place and I took her back to my place and I banged the living shit out of her all night long. I can't really get into more detail than that right now. I have to go deal with some oxtail that is cooking on the stove. It is time to get the rice going. Peace!

Time for an explanation

nospam@example.com (Ryan) — Mon, 30 Nov 2009 08:19:39 -0800

First of all I am sorry it has been 13 days since my last entry. Things have been very hectic at work and I had some family issues to deal with. I will try and avoid such long gaps in the future. I think it is time I explained more about myself and why I have spent my entire life as a single happy guy. I am a divorcee lawyer and I have spent the last 11 years handling people's divorces. I am sad to report that 99% of all relationships end up in divorcee. I always hear the same stories from divorcees that I represent. Things were always great in the beginning and slowly over time the couples were unable to tolerate the inadequacies of their partner and vice versa. My own parents got divorced when I was 13 years old and I spent from 13 to 18 living with my father who was a criminal lawyer with a very big firm. I watched him get remarried 4 times and each time have it not work out and my father lose more and more of his fortune he had built up as a result of these money hungry donkey whores. Ok, maybe that rhetoric is a bit harsh but those are his words and not mine. He has vowed to never remarry, and yet he has a girlfriend right now that is only 41 and I have a feeling he is going to get married again. It is very difficult for me to watch him be a sucker to love when he is so strong and so successful in virtually every way except when it comes to women. Women are his kryptonite. I hope that better explains why I am the way I am and why I am still single and loving it after all these years.

This weekend that just passed was not bad. Went to a friend's cottage on Sunday and we got drunk as hell and drove around on his property on some 4 wheel atv's and had a grand ol time. There were 8 of us over and later that night we played poker and got hammered out of our minds. I woke up in a corn field. Good times.

On Saturday night I went on a date with a 31 year old nurse named Rachel. She was very hot and was every male patient's wet dream. I bet she helped a lot of people feel better just by being so hot and tending to them. She must get hit on 10 times a day working in the hospital. She is a natural blonde, tall and curvy, with large natural tits. I had to play things real smooth not to let on that I was super attracted to her. I decided against picking her up in the ride and instead met her at the restaurant in a taxi. I told her to meet me at 7pm at Custom House which owned and operated by my good friend Shawn McClain. Ok well he isn't my good friend but I have met him a few times at parties with mutal friends. Reservations were for 7:30 which was good because she showed up at 7:20 - I was sitting there wondering if I had got stood up. She was all apologetic and I thought this is good, I have her right where I want her.

We had dinner and talked for quite a long time about bullshit stuff like politics and the world etc. She didn't act like the typical personality of a nurse. She was not as empathetic as I thought she would be. She was very witty and a bit of an intellect and I was starting to get curious why she was just a nurse and not a full fledged doctor. She told me that she dropped out of medical school and then eventually went back and became just a nurse. I could tell she didn't really want to get into the details so I just left it at that. She said that she was in a relationship with a guy 3 years ago and they had been together for 5 years. She said that she left him because he was not satisfying her and she felt that she had made a mistake hooking up with him.

After dinner we went for a walk through the city but it was kinda chilly out. So we popped into a 24hour coffee shop and drank coffee and chatted until about 1am. I wasn't really getting any sexual vibes from this girl... maybe because she was too busy talking. She liked to talk A LOT. I'm not sure if I could handle too many more dates like this one because I am not big on listening to girls talk. I don't want a relationship with a girl who talks so much, however, she is really hot and I was really attracted to her so maybe I could just pretend that I am listening to all her jibber jabber. I AM looking for Mrs. Right, or at least that is what I tell people, but with my childhood and with my current profession swaying me, I may just be saying this and I may just be in denial. Anyways, we took a taxi to her place, we shook hands and she left. As hot as she is, I'm not sure I wanna go out with her again or not.

A return to Spanish roots

nospam@example.com (Ryan) — Tue, 17 Nov 2009 14:43:30 -0800

On Friday I took out that girl Maria I was talking about. I picked her up at her condo to take her out for dinner and on the way to the restaurant she was ranting and raving about my car. I drive a E55 Benz... if you aren't familiar with this car, just google it. So we arrived at Alhambra Palace Restaurant on W. Randolph St. The place is basically Middle Eastern and Mediterranean food with lots of Moroccan dishes. It is not my typical kind of place. I personally prefer to eat at French and Italian places or sushi.

She really liked the place and was commenting on how it reminded her of Spain. I was happy to be able to give her a nice experience. My only worry with this girl was that she seemed TOO impressed with everything and I was feeling like I was on a reality show like the bachelor etc where the girl gets so wrapped up in all the luxury settings that they get a false sense of what is going on. I am really used to eating in expensive restaurants etc so for me it was like whatever. I think I need to be more careful with the girls I choose because she seemed a bit naive and immature.

The food WAS quite good, I had some kind of simple chicken dish with green peppers and some sauce with some rice etc although just typing this makes me think of what it's like to eat really good risotto and the next date I go on, we are definitely going somewhere that makes great risotto. She told me a lot about her country and how different it was from Chicago. She said she had a really big extended family and that she missed them a lot. I am always very cautious about girls that go on and on about hanging out with their family.

She said she was a big fan of The Smiths and Morrissey and I nearly fell out of my seat. I have never met a girl that likes Moz so I was like wow this girl is cool. She said her favorite song was "That Joke Isn't Funny Anymore" and I told her that my favorite song was "Jack the Ripper" (it's kind of rare, download it) She also said she loves to watch Survivor on tv which I like too. There WAS something about this girl that was rubbing me the wrong way though. Perhaps it was her crooked smile or perhaps it was this lurking suspicion I had that she might have a kid or some other crazy thing from her past.

I wasn't sure how serious I wanted to get with her. When we were leaving the restaurant she grabbed my hand and I was like oooooooo kkkkkkkk I guess she is really into me. However I wasn't sure if she liked me or if she liked the "idea" of me and my flashing car and clothes. As I was driving her home I was thinking... hmm I could easily bang this chick... should I? Or could this girl become a stage 3 clinger (Wedding Crashers reference lol) I kept looking at her curvy hips and was like hmmm ok.

I just drove straight to my place and she was like oh. I was like yeah. She was like I see. We went upstairs and I poured a few drinks for us. After about 15 minutes of being in my pad we started to kiss and after a nice long passionate kiss, she slowly slithered down to her knees and started to unbuckle my belt.

It was a good night

Branching out

nospam@example.com (Ryan) — Fri, 06 Nov 2009 07:43:51 -0800

The amount of girls I meet online is ridiculous. Perhaps I should not have put in anything about me being a lawyer etc because I think that is the main reason I get so many inquiries online. I like to think that I am a decent looking guy, but I got a feeling that that is not the reason for all the inquiries. I guess everyone is looking for security and money is important. So far, I have not dated any weird ethnicity girls yet. I have pretty much stuck to white girls but now I am thinking I should branch out and give some of these other girls a chance... wow that sounded so conceited lol. Anyways, I went through all my requests and I selected 6 girls who I normally would not ever go out with. I haven't had much luck with white women yet in terms of trying to find someone I am compatible with so why not... lets give it a shot and see how it goes. The first girl is named Maria and she is latin. I'm not sure exactly from where, but she has olive skin and dark hair etc. She is lean but she has some nice curves, like all latin girls do. In her profile pictures she is wearing skin tight pants - big shocker there lol. So my plan is to go on a date with each of these 6 girls and if I have no success than I am going back to nothing but white girls lol. So I am going to take her out for dinner tomorrow night and I am not sure if I should take her to Charlie Trotter's on Armitage Ave. or if I should take her to Brazzaz on Dearborn St. Both of them are high end places, but I think I might go with Trotter's because I doubt that is the kind of food that she is used to and I want to see how she behaves outside of her comfort zone. I will probably take her over to 404 Wine Bar since we are going to be in the Lincoln Park Area. I will let you guys know how it goes

Do lawyers fall in love?

nospam@example.com (Ryan) — Tue, 03 Nov 2009 22:31:13 -0800

Do lawyers ever fall in love? I am 37 years old and I live in Chicago. I work for a prestigious law firm, and I live in the North Shore of Chicago right off Sheridan Road by Chicago’s East Rodger Park neighborhood. I used to live near the lakeside Calvary Cemetery into Evanston. I have never been married. I do go on dates all the time, I do meet a lot of women, I just don't find any of them very interesting. I really want to meet a girl who will like me for me and see past all the fancy lawyer stuff. Good looking, classy, Chicago Cubs fan... I know she is out there. I have decided to take it upon myself to start meeting girls online and taking a different approach at finding Mrs. Right. I've been on a few dates already and things are getting more interesting so I decided to make this blog to document my life as a single man trying to find mrs right online. I don't know if anyone will actually read this blog, but hopefully I can help clarify what its really like to meet people using online dating sites.