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?

(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…)

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…)

I received this forward the other day and it’s too funny not to share.  This was apparently written by little kids (and my thoughts).

HOW DO YOU DECIDE WHO TO MARRY?

“You got to find somebody who likes the same stuff. Like, if you like sports, she should like it that you like sports, and she should keep the chips and dip coming.”

• Alan, age 10 (don’t forget beer pal)

“No person really decides before they grow up who they’re going to marry. God decides it all way before, and you get to find out later who you’re stuck with.”

• Kristen, age 10 (my dating a religious person article is for you)

WHAT IS THE RIGHT AGE TO GET MARRIED?

“Twenty-three is the best age because you know the person FOREVER by then.”

• Camille, age 10

“No age is good to get married at. You got to be a fool to get married.”

• Freddie, age 6 (have fun at that star trek convention) (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…)

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…)

One of the great ways to meet someone new is to dip into the the pool of your own friends network.

Always a tried and true path, trying to date someone that already has your friends approval puts them a few steps ahead of a random that you meet on your night out.  As long as your friend has decent taste in friends… which I would hope you think so… then it never hurts to roll the dice and give it a shot if you think a mutual friend could be a potential interest.

The sticky situation can occur when things don’t go as scripted.  Their phone calls spike past ‘ok freak, ease up’ volumes, and you realize that there is no way you can see any potential.  What happens when it doesn’t work out? (more…)

Recently a friend of mine met a guy with whom she immediately felt the ‘spark’.  She said he hit home on all fronts of her mental checklist and they had a great vibe.

Once he had her hooked in, much like the underrated caliber of Subway Choco-Chip cookies, he threw down the surprise of a century.  He asked her to a wedding… for a first date.

Now I’m not too sure what was going through this guy’s head.  How does asking a girl to meet your family, entertain your friends, AND get to know you on first date help your chances?  If anything, something like this will get a girl running faster than if she had the hounds of hell nipping at her heels.

So this inspired me to come up with a weekly treat for these people.  We’ll come up with ideas for a potential date and discuss the pro’s and con’s.  Since I’m not creative with names, we’re going to call the series “Weddings are a Terrible First Date”. (more…)