Introducing...

Chi-Town.

It was my second free Friday of wedding season. I had dropped baby boy off with my mother, and was faced with endless possibilities of what I could do with my free Friday night. Earlier in the day I had been overcome with a horrible migraine. The only way for me to get rid of migraines is to sleep...so sleep was option number 1.

Option 2 came in the form of seeing live music. A friend of a friend had a band that was playing at a local dive bar. I don't get a chance to hit up the local dive bar scenes, especially to see live music, very often.

I chose option 2.

The weather was eerily stormy. Minnesota is in the midst of a pretty intense drought, hence any form of precipitation completely caught me off guard.

When we walked through the doors, a man in a yellow-gold shirt caught my eye.

Tall -> Check.
Proper Hygene -> Check.
Lack of wedding ring -> Check.

Enter: his guy friend....Not gonna lie, the second I saw He was with another guy (without any girls in the picture) I jumped to the conclusion that he was Gay. Yeah, I'm going to hell and that was extremely closed minded of me...but hey, I was just doing my best to keep it real and not waste my time.

The girl I was out with, B$, immediately had her eyes on his friend (it's amazing how some things work out!).

Before long, B$, myself, and the two boys were talking. Yellow shirt was from Chicago (Chi-Town), and was a HUGE White Sox fan (I told him I was sorry to hear that..hehe). The only awkward thing about our first conversation was he immediately said "Well..I kind of have an ex, kind of not...I don't know, it's really confusing."

The boys hung out with me and B$ the rest of the night, engaging us in a couple of games of Foosball, and even helping me win a silly stuffed animal in a claw machine. They came with us to a different bar where talking was a lot easier to do. We invited them to B$'s house (which is quite out of character for us to do), and told them they could come over only if they picked up White Castle.

An hour later, they arrived at the house with White Castle in tote (it was awesome and adorable).

Soon after we were done mowing down, B$ and her beau found themselves engaged in a kiss/mini make out session (which was cool...but left me and Chi-Town in a bit of an awkward position).

I could sense the awkwardness so I did what I do best, and had us go to a different area of the house where we wouldn't have to worry about interrupting anyone. We drank, we sat, we talked.

He had been in a 5 1/2 year relationship. He had moved to Minnesota for her. She moved out on him about five months ago. He really didn't divulge too many details..and I wasn't looking for them. All I knew was it was wonderful to hang out with a guy one on one, no pressure, just good and light hearted conversation.

I hadn't mentioned my single-mom status, but referenced how I know what it's like to feel like you have baggage (referring to his mental baggage, and my "with child" baggage). He asked me to elaborate, and I'm not one to lie so I told him an abridged version of my current life situation. He sat. He listened.

I found out his age, which threw me by surprise because he was nine years older than me, but didn't look it in the least.

As the hours passed we ended up in B$'s spare bedroom (no worries, we didn't sleep together, remove any clothing...we literally were wiped out looking for a place to crash). We laid on her small twin bed, him on his back, myself on my stomach looking up at him. He was adorable. He was comfortable.

We couldn't decide if we should try to sleep in the twin bed, or try to sleep on the floor. By this time, the sun had been up for a couple of hours, and sleep was desperately needed. After moving to the floor the bed was definitely the best option. As we were about to get back onto the small bed, it happened. He went in for a kiss, and I happily obliged.

It felt amazing to feel a man's lips on mine. My head fit right into the nape of his neck. I'm not sure where his motives came from, and believe you me I've been analyzing every second of it!

• Did he kiss me out of convenience?
• Did he kiss me because he was actually interested in me?
• Did he kiss me to prove to himself that he still had it?

...I can't be too sure.

Me, being the most un-suave person I know, never managed to get his phone number. Thank god for B$, as she got his friend's name and number.

I don't know if anything will come of Chi-Town. I haven't even been pining over him like I typically do over most men that cross my path. I think I'm being realistic with him. The cards don't seem to be playing out in my favor, but I'd be darn tootin happy if he proved me wrong and made another move. A girl can only dream.