The Bad Dates That Make You Never Want To Settle

This is one of those stories where you look back and ask yourself: “What the f*ck was I thinking? If you’re broke, the last thing that you should be trying to do is date someone. That’s a lesson that a guy who was as sweet as can be learned when he met me. We met at a friend’s house. You know the usual, drinks, shit talking, good music. My little short self met his eyes, sized up his chocolate skin and 6-foot something frame and liked what I saw. We hit it off immediately. Me being a somewhat accomplished college graduate and radio personality…and him an ex-felon still living at home with his mom.

He caught me at a time when I was just healing from a breakup: 4 years we were together, but that’s a story for another day. Anyway, I figured it would be nothing serious, so we exchanged numbers, had a couple of more drinks and went our separate ways. He gave me a call about a week later inviting me to the annual African festival. We went, but instead of him taking me through the main entrance, he snuck me through the side entrance — because his friend was the security guard. I thought it was a nice gesture, but I was no fool. He was broke, but needless to say I was lonely and wanted the company.

He would come over to my place and chill. We would eat, watch movies and converse about the day’s events. I had my mind made up that he would be in the friend zone, at least until his record was expunged and he got a job. Silly me.

One Sunday he called me up and invited me to a comedy show. The show started at 6:30 P.M. and the doors opened at 6. He suggested that I pick him up, yes I did all of the driving, promptly at 5 P.M. I arrived at his home around 5:30. He already had the tickets so I figured I had a bit more time to get ready. When I picked him up, he seemed frazzled and uncertain. I look to him and asked him if he was okay. He said yes as he looked out of the window.

A few minutes went by and I asked him if he’s okay again. He then informs me that the tickets are first come first serve, that there’s a line and we must be in the front for guaranteed entry. I pause and say, “Well, how much are the tickets?” “$10,” he responded. I said, “Okay, well. if we’re late, we can just pay.” To which he responds, “I was going to ask my mom for some money but…” I grew silent. Silent because I put myself in this position once again. Silent for dating someone who shouldn’t be dating in the first place. He’s trying. That’s what I tell myself.

I pulled up to the comedy club, and the line was wrapped around the corner. I sighed. We’re not getting in, and I’ll be damned if I pay for him. It’s enough I had to drive. My friend texts me saying that I should ditch him and go to the movies. The new Tyler Perry film is out, and at least there would be no surprises because I know I’d only have to pay for myself. My mind is made up: “If we don’t get in, we’re going home.” He just looked at me. We’re standing in line. I’m watching people pull up and go to the front of the line. VIP. Tickets bought, no line, no wait. “How’d you get the tickets?” I asked. “My pastor gave them to me.” He’s so creative. He’s trying Shantell. Go easy on him.

After about 45 minutes of waiting with very little movement, one of the comedians came out and started to interact with the crowd. “The first person to tell me when I was born gets to skip the line…” July, January, March the crowd tossed out just about all of the months of the year. I pull out my phone, google his name and his Wikipedia page comes up. ”December 15th, three days before mine,” I scream. He looked my way and said, “Come on.” That’s how we got into the club. Shantell saves the day once again.

As we enter, I asked him if he wants to get a drink but then I remember that he has no money. I got water, not wanting him to feel left out. We stood and watched the show and a man with a familiar face appeared on stage. Ahh yes, I remember you sir. We met on a bus and you’ve been trying to get me to go out with you for about a month now. Damn. You’re up there, looking kind of good. Haircut, making people laugh. I bet if I was with you, I’d have my drink and my seat and my VIP ticket. But I’m not.

I looked to my left at my “date.” I’m not sure if that’s what I should refer to him as at this point but regardless, I was with him. After my comedian friend finished his set, he came up to me and greeted me with a smile. Damn AND he smells good. Why didn’t I go out with him again? We hold a two minute conversation, neither or us acknowledging my date. It was rude, but I was annoyed. Mostly with myself for settling. We wrap up our convo; he offers to buy me a drink. Once again I decline out of respect for my date.

We finished the comedy show, barely uttering a word to one another. The tension a bit thick; me annoyed, him feeling shame if I had to guess. The ride home felt like a funeral procession. Silence. Deep thought. He broke the silence. “Did you enjoy the show?” “Are you forreal? We would have missed the show if it wasn’t for me getting us in.” That’s what I wanted to say. What did I say? “Yeah. It was cool.”

I dropped him off at home and pulled off. Thinking about my love life. The ex who I just broke up with two weeks before my birthday. Wondering if I’ll ever find someone like him. Someone on my level. My equal.

Needless to say I didn’t hear from my date for a few weeks. When he called it was his birthday. He wanted to have a drink. We kicked it (at my crib, of course) and acted like the incident never happened. Today, we’re good acquaintances. He appears to be working, at a clothing store and has had quite a few girlfriends since then. And as for me? Still solo, but nevertheless happy and never ever settling for someone less than what I want again. Thought Catalog Logo Mark


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