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On Monday I sent a desperate email to my friend Michael to encourage a friend of his, an acquaintance of mine, to take me out for my birthday. I figured Michael would not even email me back because he is busy with his own life but he called me later that day asking me what I wanted to do for my birthday. He had arranged for another friend of his Scott, a local comedian, to take me out. I was pleasantly surprised and happy to have plans for my birthday. Scott and I chatted that night on the phone and made plans for Tuesday night, my birthday. Between chatting on the phone and checking out his Facebook page, I was looking forward to hanging out with this guy on my birthday. I think there is a big potential for a comedian, or any performer, to feel like they are always on stage, and give you a performance instead of just being themselves but this guy seemed down to earth and pretty curious about me. On the agenda was dinner at Calo in Andersonville and then drinks at Green Mill. 

I wanted to get gussyed up on my birthday anyway but since there was a man who was going to spontaneously spend his evening with me I didn’t hold back. I wore my favorite dress, a red three-quarter sleeve wrap around with a plunging neck line. I did my “Bettie Page” look for hair and make up. I wore a black sweater over the dress for a work-friendly look. I had a full day of work and part of class to get through before I could have birthday fun. 

I took off from class at 7. The train ride from the loop to Andersonville left plenty of time to retouch my make up and fluff my hair. I got quite a few stares on the train but didn’t understand what the stares were communicating.

When I first arrived in Chicago the Red Line was under construction and delays were rampant. Now that construction is complete I have to relearn how long it takes to travel. Needless to say I arrived at the restaurant about 10 minutes early. This worked out good because I had time to chill before he arrived.

Scott looked and smelled great. We greeted with a hug and I gave him a peck on the cheek. The restaurant is really big but it was a slow night and pleasantly quiet. He was complimentary of my appearance and seemed happy he had decided to adopt me for the evening (side note: not sure why the word “date” freaks people out. “date” is not spelled m-a-r-r-i-a-g-e). He ordered us a bottle of wine, a Shiraz. We chatted it up for awhile and got around to ordering. My meal, stuffed Gnocchi, was delicious but his was mushroom-y. He didn’t notice on the menu that his meal would be smothered in sliced mushrooms. He pecked at his meal and didn’t drink much wine. He said he had gone out with friends prior to meeting me and had eaten too close to dinner. The dinner conversation was great. Really down to earth and chatty. I think we were both surprised that the other person seemed so cool and relatable. After a bottle of wine, a meal, and some deeelicious Tiramisu (an hour and a half) we headed to Green Mill.

Green Mill is a fantastic place. It was were Al Capone hung out when he was on the North Side. Original decor is in place and there are these cozy little booths to sit in. This is definitely the kind of place were you give your undivided attention to the music. The emcee tells you before the start of each set to keep talking to a minimum. Scott and I got there right when a set ended and sat at the bar at first. We talked and flirted for awhile. He seemed to think it was odd that I did not really have any friends or dates since I moved to town. We were able to settle into a booth by the time the next set started and continued our conversation and flirting at an appropriate volume.

We stayed through the second set and then headed back to his place. I will leave the rest of the evening to your imaginations.

I sincerely enjoyed my evening with Scott. He is a cool person that I hope to hang out with again. In addition to meeting a cool person, the evening was a nice reminder that life is good here in the Chi.

I need to give a special shout out to my friend Michael. This is just one of many times he has gone the extra mile for me.