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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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…)

Don’t dip your pen in company ink.

Don’t $hit where you eat.

Don’t throw the baby out with the bath water….  wait… that last one didn’t make any sense.

Everyone says that it is a terrible idea to date a co-worker.  Obvious reasons include if they go psycho on you, you have no where to hide.  Maybe it’ll change the work dynamic and make it terribly awkward for you and the rest of the office.

It could also end up putting your ‘feel goods’ in a vice if one of you gets promoted and has to deal with not only who wears the pants in the relationship, but now the office as well.

Even though it’s frowned upon, it happens all the time.  Spending hours upon hours a day with someone that you’re even mildly attracted to can make your mind wander to that dirty gutter that flows so freely.

If you do decide to venture down this much traveled path, just remember a few things: (more…)

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…)

Before you hop on that horse and gallop out into the sunset with your damsel, there will be a few key plays that you’ll need to be aware of that can greatly shift her perception of you.  One of these plays is early on is the first group hang out session: her group or yours.

Which should you do?  What’s the better move?  Did you have to eat chili for lunch?  All valid questions… let’s take a closer peek.

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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…)

“He’s my best friend and you’re either OK with that or you’re not.”

“I love him, but I’m not in love with him.”

“We have such a long history, there is no separating us, he will be in my life forever.”

Any of these sound familiar?

It’s in the back of your mind and you just can’t seem to shake it loose.  It’s not as if you’re talking to any of your ex-girlfriends anymore.  Every girl that has been in your past, has quietly bowed out with her time.  There are no phone calls, there are no text messages, and there surely aren’t any thoughts that pass through your head which incline you to reach out to them.

Her situation is quite the opposite. (more…)

The first few times you hang out with someone, the air is filled with ‘getting to know you’ moments.  “You love Wilco too!?  I have their entire discography!”, “You have two brothers and a sister?  That’s crazy, I have two sisters and a brother!  We’re a match made in heaven!”.

Before you know it, you’re being asked to hold their nephew’s legs at the Bris, or you’re hauled off to church in order to absolve your sins.

There is nothing wrong with following your faith if it makes you happy.  But what’s the path to righteousness if you’re not religious and the person you start dating is their respective religions favorite customer? (more…)

Things are on the up and up.  You’re on a steady once a week hang out, frequent phone calls, and the text messages are beginning to get the everyday vibe.  Just when you think things are running smooth… Bam!  It hits you like that surprise bar tab you pull out of your pocket the next morning that rings more than just a couple digits.  Just my luck!!

A birthday.

If only it were back in the good old days.  Gather all your friends for cake and ice cream, smack around a pinata filled with candy, and play some pin the tail on the donkey.  Even if you pinned that elusive donkey’s head, you still go home at the end of the day satisfied and smiling.

Now, its a delicate game of thin ice.  Too many marbles, and the house comes falling down.  Too few, and she’ll wonder if you’re even interested in playing the game. (more…)