Last Friday, my girl and I went out for a drink at an after work networking event at Plush. Well, I run into an old friend while there. I met him when I first moved to Chicago, and as a young 22 year old, adjusting to the big city, I was busy. Busy in the sense that I had dates lined up every night of the week just about. I was checking out the scene, doing me. This guy was cool.. educated, good career, nice car, however things didn't click because he's the quiet type. There's nothing wrong with being the "quiet, shy guy," but it makes it hard for me to connect with you when you don't ask questions and give me one-word answers. You're boring me.. on to the next. I eventually just let it fade out.
We're catching up and he asks, "whatever happened to us?" I simply give him the response that we didn't end things badly, it was just matter of we just phased out. He wants to hang out from time to time (meaning "let's pick things back up"). No problem, I guess. Maybe things have changed in 4 years.. I'm not convinced but why not?
We go out and hit Tantrum up for $5 martinis last night. Sidenote: If you're ever looking for a swanky spot for good drinks, def hit it up on Mondays. Great martinis, cool atmosphere and they'll play your iPod! Downside is that they don't serve food and you have to order from a spot that delivers.
So back to Tantrum. I'm thinking cool. Haven't been here in a while plus I will have the opportunity to find out if there's a connection between us. Wrong! He invites his homeboy up there to have drinks with us.. and I'm feeling like the third wheel as they talk about sports, video games and their friends. I'm able to hold my own in any situation or conversation, and not look bored.. however it was blowing me that his boy is with us having drinks. If I'd known this, I surely would have invited one of my girls out with us. But wait people, this is not the first time this has happened. When I thought back on our past, he had invited another friend to meet us out. I'm confused because he has great qualities and I'm wondering does he not feel comfortable in a date setting? He's 30+ so the group dates or having the boys tag along are a in total violation. And it is also a total turn-off and I'm not even sure if I even want to move forward with seeing him.
However, what is going on here? Is this man not comfortable to left alone with a woman? Is he just trying to send the signal that a woman in his life will always play 2nd fiddle to his friends? And if he's inviting friends, why isn't he relaying the message that I can invite some of the girls out?