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…)

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?

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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!

Living in the city has some great perks.  We have the beach at a stone’s throw, festivals to fancy anyone’s delight, and different nightlife activities to cater to even the unique of circles.

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? (more…)

I wrote a guest post for a great blog called Sex, Lies, and dating in the City by Simone Grant (check it out, it’s very well done).  The story was about how you can have blinders in a relationship.  Here it is:

To this day I still can’t figure out what it is about being infatuated with someone that allows one to become so oblivious to seeing red flags.  I’ve personally always lived my dating life to a three red flag system.  It normally never fails me: three flags and you’re out.

Some of my previous red flags have included a girl handing me a toothbrush the next morning (first night together) saying “I always have a spare toothbrush for my overnight guests.”  Really?  When did I check into a hotel?  To a girl who spoke the entire time during a date and allowed enough gap in the conversation for three words:  “Hi.” and “Check please.”.

This one girl in particular that I dated, Sarah, was my devil in a red dress. Despite the abundance of flags thrown, I wore my blinders on snugly and marched forward. (more…)

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!

The success of a night out on the town is completely in the eye of the beholder.  Some gauge it on the pleasant conversation, some the chemistry and future prospect, and others… the horizontal tango.  Often times during that first encounter, the act of slowly becoming three sheets to the wind is briskly followed by an intimate encounter between the sheets.

So what’s next?

Besides the sometimes awkward exchange in the morning, trying to remember their name, or possibly floating on cloud nine (or stumbling across it), one might often wonder… does this have any real potential? (more…)

So I was running through some funny clips on youtube and came across this one that I thought would be a good way to show people on what NOT to do for a dating video.

Best line: “I deserve love like everyone else! I dont need to rummage through the dumpster for a playboy!!!!!!”

While this is a fake video, I wouldn’t be shocked to see some people actually do this.  Seen any that are too good to not share?  Send them over or post them in the comment section!

The question has been asked many times over the ages.  Due to the amazing scenario if actually pulled off correctly, it can leave us perplexed, wishful, and sometimes even waking up in a room next to the very person to whom this article is referring: the opposite sex friend.

Many say it can’t be done, citing the inherent need to procreate that is hardwired in each and every one of us… men AND women.

The fact that one can very easily become attracted to someone after spending a large amount of time with them doesn’t help by adding fuel to the fire.  This is one of the major reasons why workplace flirting and banter often leads to wedding bands and white picket fences. (more…)