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!

Halloween is a fantastic night in Chicago.  Plenty of Chicagoans are dressed up, out and about, and geared up in party mode.  This is a great night to go out and meet a special crush out on the town.

Do you have your costume yet?

If not, here are some places you can hit last minute to throw something together.

Salvation Army Thrift Store – 2270 N Clybourn Ave, Chicago, IL‎

Always full of the most random pieces of clothing and accessories, this is a great place to hit up that won’t break the bank.  If you are going to go here, make sure you have a reasonable plan of what kind of costume you want.  There are so many types of clothes and strange items, your head will be spinning and you’ll feel like you’ve walked into a life-size version of that old smelly box full of random crap in your parents basement.  (more…)

Sometimes, people just don’t have the guts to break up with their latest crush in person.  While there are certain rules to when this can and cannot be done, generally speaking, if the relationship is very young (a couple weeks), it is not necessary to break up with someone in person.  But what happens if you know it won’t work with this person and have no desire to call them up and let them know they didn’t make the cut? (no guts, yes. does it still happen? absolutely.)

Enter: The Phase Out

The phase out occurs when you gradually remove this person from your life.  Like a dying heartbeat, the tempo and rhythm of the short lived relationship pace themselves slower and slower.  Text messages become ‘no-response’ statements instead of questions and phone calls become a rare gem.  While there is nothing you can do on the receiving end of a phase out (dust yourself off kid and get back out there!), there are a couple keys when implementing it so you don’t come off as a complete jerk (or bitch).

1. Have a plan – Once you decide that watching paint dry is more entertaining than this person, commence the phase out and stick to it.  Start hitting the brakes and slow that train down.
2. Keep it gradual - Slow and steady wins the race (or in this case, douses the flame).  Draw out the texts and ease up on the calls.  Baby steps.
3. Avoid weekend dates – If you’re going to hang out, hang out during the week.  Weekends are prime real-estate, and you don’t want to play with fire after drinking… which leads to…
4. Don’t have a sleep over – This just resets the clock at zero.  Everytime you get it on between the sheets, it sends a signal to the other person you’re in it to win it.
5. Axe the late night calls and drunk texts – “What you up to?” at 2am isn’t as innocent as your drunk mind convinces you.  Have a little restraint or else you’re back at square one and just extending the phase out.

Whatever your opinion of the phase out might be, it’s still a tactic that is used in the streets of Chicago and many other cities around the globe.  Do you phase out?  Have you been phased out?  Share your thoughts in the comment section!

What’s a better way to spend an evening than drinks and a movie?  How about drinks and a movie with a bunch of other people at the Vic!  This is a great way to hang out in a relaxed environment, not spend an arm and a leg, relax with a beer, and watch a great movie.

The Vic Theatre is typically a concert hall but on their off nights they’ll use the space to project a movie and fill your belly with cheap beer.

They play solid movies that range from new releases (the Hangover-which if you haven’t seen it, get out from under your rock and GO) to classics like Animal House and Office Space.

Here’s a link to their website: Brew and View

Overall – 4/5 Stars

While not a terrible idea, buying drinks for girls isn’t the most inventive or memorable way to introduce yourself to a girl.

Here’s the part that threw me off my game.  The past few weeks while I’ve been out, I’ve had two girls walk up to me and say “Want to buy me a drink?”.  Personally, the first thought that goes through my head is “Are you serious?  Get lost lady.”  Do guys actually fall for this?  No matter how attractive or unattractive the girl is in this situation, I find it to be completely obnoxious and she’s thrown all credibility out of the window faster than a starving fat kid devouring chocolate cake.

If I were going to buy a girl a drink, it would be after we’d been talking for awhile and there is obvious chemistry or solid conversation.

Ladies, do you actually see any success with this?  Or are these ladies just crazy?

Share your thoughts in the comments!

What does that mean?  Never heard of it?  Did I just make it up?

National Singles Week was started in Ohio back in 1984 to appreciate and acknowledge the growing number of unmarried Americans, who are now 96 million strong, or 43 percent of the U.S. population age 15 or older, according to the U.S. Census Bureau.

I’ll just consider it the opposite of Valentine’s day.  For all those singles out there who feel that twinge of envy when their coupled counterparts are celebrating on that red velvet night, now’s our turn to rock out.

The only thing is, we get a WEEK instead of a single night.

So break out the party streamers and the secret booze you keep hidden in your drawer at work.  It’s time for a celebration.

I’ve combed through and found some good places to hit for happy hour each night so you can go hang out with that support group of yours and soak in your freedom. (more…)

When I think of museums, one of the first things that comes to mind is this pleasant scene from one of the greats… Ferris Bueller’s Day Off.

We could all use one of these days every now and then.  While that movie has plenty of date ideas scattered throughout (ball games, obnoxiously fancy restaurants, and doing a rendition of Danke Schoen on a float), the countless museums around Chicago are all possible date locale’s for that first time encounter.

Let’s break it down… (more…)

In the spirit of Chicago summer’s, despite how short it has seemed this year, this week’s date idea is festival’s.

There are many different flavors of festivals out there.  From relaxed culture centric, wine festivals, to great opportunities to meet other singles at the Old St. Pat’s fest.  Whatever you are looking for, these festivals are a great place to take a date due to the high level of interaction, social aspect, and the relaxed atmosphere.

Here’s the breakdown:

Pro’s –

People Watching – Walking around at a festival rivals the entertainment walking around at an airport.  Somehow it always seems to draw the most interesting of people.  Whatever your style is, you’re bound to find the opposite at different festivals, and that always makes for great people watching. (more…)

For those of you who missed last week’s first date article, I’ll be doing a series of potential ‘first date’ options and breaking down the pro’s and con’s of each.  Due to the **sarcasm alert** impressive move by one of my species who asked a friend of mine to a wedding for a first date, I’ll continue throwing out ideas for first date options with a few venue locations at the end.

Today’s date idea: A Comedy Show

Pro’s –

Humor test - You’ll get a feel for their humor.  If you’re laughing at the same times, it’s a great sign that you’re both on the same wavelength when it comes to humor.  This can sling the doors open to favorite TV shows, movies, and embarrassing stories of the past. (more…)

One of the perks of being a grownup, in addition to buying candy without asking for permission, is the ability to choose your own friends.  If a person rubs you the wrong way, you don’t have to join their softball team or put up with mindless chatter about the always interesting Chicago weather.

It’s the ultimate power that is often taken for granted.  Don’t like the way I talk?  Then get lost pal.  Oh it bothers you when I talk about something other than your life?  Then scram!

The one time this situation gets sticky is when your lady’s friends are the enemies you’re trying to swear off.  She wants you to meet up for drinks with her gals, or even worse, spend the day with them while you’re stuck thinking of a hundred different excuses that will get you as far removed from these creatures as humanly possible.

How and why should you have to put up with this? (more…)