One of the most fun date’s I’ve had in Chicago was at a Jazz club.

We went to Green Dolphin Street for our night of class.

It was a nice, relaxed dinner while listening to a fantastic jazz band.  I felt like I was in the backdrop of an old film… where I should have been wearing a top hat and trench-coat amidst a cigar-filled room.

Here are a couple places to check out around town for some top notch jazz.

Andy’s Jazz Club

Downtown and right next to a bunch of other bars and spots to hit afterwords.  Great spot for dinner and a cozy setting that sits you right next to the band.

The Joynt Chicago

Dark and sexy, this place is a nice spot for a cocktail with some soothing background music.  The music has been stellar and the overall vibe is very cozy.

Kingston Mines

This is more of a social spot.  Open late and plenty of room to spread out.  There are two stages here that trade sets hour after hour.  So if you don’t get a good spot the first time around, hop over to the other side and feel that music!

Let’s paint a picture like Bob Ross.  Only this painting isn’t going to have happy trees and a secret bush that only we know about.

You’ve just started talking to this girl and it’s still fresh… maybe just a month or two.  A handful of dates and a couple sleepovers.  During your disheveled stay at her place, you’ve met the roommate and the playful banter has begun to move one notch above ‘friendly’ in your mind.  You may find yourself laughing with her more, have a easier flowing conversation, or even simply find her more attractive.

Entree envy.

This puts you in a very sticky situation.  What are you going to do if the roommate is a better fit for you than the original? (more…)

I stopped by this hot spot recently and was definitely digging the vibe.

The Violet Hour in Wicker Park.

This hidden gem has a dark, trendy atmosphere that is sure to promise for a pleasant evening.  Even if you might confuse yourself for being in a giant game of Tetris (the high backed leather chairs look like “L’ pieces and all tables are small perfect squares), the drinks are impeccable and the intimacy is just right.

While I wouldn’t say this is an unknown spot from reading the crowd, it’s for sure a good place to stop by for a quiet evening of getting to know you.

The Violet Hour – 1520 N Damen Ave

On what NOT to do…

This is a hilarious video from the 80’s with online dating videos.  I don’t understand how some of these people can say this stuff with a straight face.  Maybe it’s the radical mustache or the bodacious hair that gives them the sharp intellect to spout off favorites like “I’m a 25 year subscriber to Playboy” and “I consider myself a refined valley dude.”

“Hi Mom!”

If you’re tired of the drinking that can sometimes make your liver pack up and move out of town, something a little low key can always make for a great date.  A coffee shop is a great place to stop, grab a non-alcoholic beverage, and relax with your date.  It allows for great conversation and is a great atmosphere to get to know each other without having to scream in each others ears as you would at a bar.

Instead of running the typical play and taking her to a Starbucks or Caribou Coffee, opt for a something a little less commercialized and check out these hot spots around town. (more…)

Your apartment has become a revolving door.  Like the office buildings in the Loop, you’re beginning to check them in at the front counter.  Fill out your name, who you’re here to see, and the time you arrived.  Here’s your visitor pass with a crappy photo of yourself and please… wear it proudly for all to see.

Finding potential love interests tend to come in waves.  Both sexes have an extraordinary sense of hunting the other when they’re taken.  Call it dumb luck, a hormonal hurricane, or simply confidence.

So what are you to do when you’re dating a few different people at the same time?

(more…)