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!

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?

You need to put that thinking cap on and make an executive decision.  If it’s new and you’re already checking out other girls, is the original girl really a keeper?  Draw a line in the sand and pick your side quickly.

If you decide that you’re not feeling the original relationship, break it off immediately.  Wait an appropriate time, maybe a month or more, before you approach your new crush: the roommate.

Otherwise, if you decide that you like the original girl better, cut ties and especially the flirtatious side with the roommate.  You don’t want that mess on their hands.  With most roommate situations, there is full disclosure, and if you push too hard you could get burned.

Remember if you break it off like a jerk, such as implementing the phase out, you could hurt your chances of picking up the roommate later on down the line.  Tread carefully!

The switcheroo is a difficult act to pull off, but it can be done if done with extreme care, planning, and precision.

Have you ever been through something like this?  Did you successfully pull it off?  Sound off in the comments below!

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

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!”

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.

Jupiter Outpost
1139 Fulton Market Avenue

An outfit that always has a place to sit, relax, and sip on that liquid coffee bean.  They also have food so if your date lasts longer than your drink, you can fill your belly by choosing from their well rounded menu.

Julius Meini
3601 N Southport Ave

Great place for coffee or even brunch.

Savor the Flavor
2545 N Sheffield Ave

Small place that is cozy and comfortable.

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?

At the beginning, your confidence is riding high.  You like all of them, and you’re not sure which to cut.  So you continue to juggle all of them throughout your week.  Tuesday, Thursday, Friday, Saturday… the days are filling up quickly, and the pressure is increasing due to you keeping them all a secret.

Unlike The Bachelor, you aren’t required to eliminate them each week… but it may be a good idea.

Be wary on the extent of how far you go with each of them.  You don’t want to be the town bicycle that’s sleeping with three people at once.  The line of discretion enters once you have slept with someone.  Other than that, if you are just hanging out and dating, make sure all parties know you’re not in for a serious relationship.

Being honest, with yourself and others, is the key in this situation.  With others, make sure they know you’re not tied down at the moment.   And if things get too far, make sure you either cut the others, or let them know that you’re seeing other people.

While there is absolutely nothing wrong with playing the field, it’s best to evaluate and eliminate.  Figure out quickly and use your focus on one person.  Talking to multiple people is a great way to figure out what you like and what you don’t like.  Ride that wave… just make sure you pack that protection.  Sun tan lotion is always a must!

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. 

Ragstock – 812 W Belmont Ave, Chicago, IL‎

Ragstock is great for looking for vintage clothes.  With 70’s, 80’s, and funky clothes, you’ll be able to put together a solid costume in no time.  They have a large variety of clothes and it is reasonably well organized, so you don’t have to hunt and peck as you would at a Salvation Army store.

Halloween Hallway – 222 S Wabash Ave (more locations)

This is your spot for your set holiday costumes.  You can take a stroll through here and get a bunch of different ideas for what you want to become for the night.  Especially good for those who are heading to a party Saturday night, but have NO clue what they want to be.  Walk in, purchase costume, walk out, wipe hands on pants.  Simple.

If you have any other places for costumes that could help out your fellow Chicagoans, let us know in the comments!

Happy Halloween!

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!

Bin 36 is a great American cuisine restaurant that holds an event about once a month called “Movies in the Loft”.  While dinner and a movie might be a little cliche, it is definitely a date that will occur at some point in your fresh new relationship.  If you’re going to do it, do it in style…

Instead of taking your crush out to dinner and cabbing your way to a movie theater, why not kill two birds with one stone?   These events have a 3 course meal coupled with some wine that will keep your belly’s pleased while your eyeballs are entertained.

They play classic movies, the two upcoming being ‘Guess Who’s Coming to Dinner’ and ‘Bottle Shock’.

The next event is coming up on November 22nd, for more details click here.

Overall – 4/5 Stars

This leads to meeting many different kinds of people… tall, short, strange, beautiful, different races, religions, ethnicities, and so on…  Which helps us create a mental checklist of things we want and don’t want in a potential partner.

Straddling the line of staying in the game and being kicked to the curb, lies the deal-breakers.  With so many options, which breakers are valid, and which are part of your own neurosis?

The Core Checklist

These are the mainstay of your livelihood.  Whether its religion, family values, or perhaps even race, nothing is going to shake the roots of this tree.  Keep these values strong and do your best not to waver from them.  Dating is hard enough as it is without having huge looming back-breakers tracing your mind on a daily basis.

Even though one could be open minded, both parties must have their heads and hearts open in order for this to have a shot.

If she’s a hardcore Catholic, and he’s a practicing Muslim, realize that both of you aren’t going to be praying to the same forces when the Cubs are down by a run.  Like the wailing baby on an airplane, the core checklist is difficult to ignore, even if you blast your Ipod, you’re still killing your ear-drums.

The Adaptables

So she doesn’t like the savoring glory that is Taco Bell, and he’s Big Foot’s long lost cousin with that sweater he calls hair.  While these tribulations may be more annoying than the old lady’s purse that’s digging into your side on a packed El to work, you have to learn to let it sliiiiiiiide!  Give the situation a second glance before you execute your decision to kick them out the door.

Adaptables are called such because you can adapt to them!  Ease up and you may find that even if she’s a valley girl who says ‘like’ every other word, and he has excessively sweaty palms, that good could outweigh the bad.

You could even get used to it and find it to be one of the things you really enjoy about the other person.

The X-factors

“His nose hairs are scraping my face when we kiss.”

“She wears so much makeup, I feel like I’m dating Bozo the clown’s daughter.”

Neither of you are perfect, get over it.  The X-factors are the little things that can be adjusted over time.  While they may be glaring problems to kick it off, they’re usually more problems in your head than they are in reality.  If they chew with their mouth open, a disguised joke saying that food looks better after they’ve chewed it, and boom… problem solved.

Deal-breakers will always be part of the dating arena.  It’s a huge multi-headed beast which you must face on your journey.  If you don’t realize you’re being overdramatic, you could find yourself in a boat alone; missing that perfect soul that may exist… but is just a little disguised.