Everything That Went Through My Mind Before My First Date At 30

by Reggie Wade

Most of my writing for Elite Daily has been on the subject of love and dating. Anyone who knows me would probably laugh when they hear that.  Not because they're dicks, but because up until now, I haven't exactly been successful in my romantic endeavors.

In fact, I got to the ripe old age of 30 before I even went to my first date. But that time has come and gone. At the tender age of 30, I've finally gone on my first date. Let me tell you about it.

The year 2016 has been a coming-out party for me. I've done things I never thought I would do before. My goal was to try to become the man I've always wanted to be.

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I've been to professional therapist, professional cuddlers, sex toy workshops, speed dating and even matchmakers. I've seen and almost done it all. It was embarrassing at times, it was awkward at times and many times, it was actually fun.

Out of all the things I've done, it was my visit with a matchmaker that bore the most fruit. My wonderful matchmaker Caitlin told me that finding a match would take time because she really makes sure her matches are compatible.

At first, I thought that was just a nice way of saying, “You're ugly and it's going to take a long time for me to find anyone that wants to go out with you.”

But that was not the case. That was simply my insecurity talking. The same thing that kept me single my entire life was coming out to rear its ugly head. Perhaps sensing it might lose me forever, it decided to come out for one last battle with my psyche -- like General Custer's Last Stand.

As time went on. I eventually forgot that I went to a matchmaker. And then it happened!

I got an email from Caitlin saying that she found my match.I was stunned. In fact, stunned was not the word. I was flabbergasted (which is actually kind of the same thing, but it's longer so I think it conveys more emphasis).

Caitlin sent a beautiful introduction to match a truly beautiful girl. And boy was she beautiful. I actually couldn't believe it. I (my insecurities) began to question poor, patient Caitlin.

This girl agreed to go out with me? You showed her my pictures and she actually said yes?

She certainly did. Not only did she send my picture, she actually sent the girl my bio, and it turns out that we actually have a lot in common. Caitlin said my match would love to go out. After getting her number, we sent a few text messages and our date was set.

In preparation for this momentous occasion, I knew I had to go in with a plan.

But what? I have never gone on a date before, the only thing I have to go from was TV. You have to remember one thing: I'm from Brooklyn. And no, I don't mean I moved to Brooklyn after college. I'm really from deep Brooklyn. You know Brooklyn, Brooklyn.


Let me put it this way: The bars around my way don't sell IPAs or microbrews. We have Budweiser, Coors and Corona; take your pick, drink it and shut the hell up.

I know I went on kind of a tangent there, but what I'm trying to say is where I'm from, we don't go on dates, we “hang out.” You get a girl's number, you ask her to hang and you either go for some pizza or you go for some pizza with a group of friends.

This is Brooklyn and pizza is life.

But I knew in my heart the Brooklyn way wasn't going to cut it this time; I had to do something else. I love learning, and I'm not one to shy away from asking for help, so that's what I did.

I asked almost every female friend and acquaintance I had about what we should do on our date. I got a variety of answers. Ladies, you have my undying gratitude.

So after much deliberation, I decide what we're going to do. I took charge like a man's supposed to do or whatever. Once my date agreed, it  was on. It would be a week until our date. That was a tough week -- and to say that post-election is tough. We as a nation have had a few, tough weeks.

I would go over every detail in my mind.

I would go over every detail in my mind. how It was supposed to go, how It was supposed to feel. I kept thinking to myself, “What if I mess up?” “What if I'm not handsome enough in person?” “What if I'm bigger in person and she's not into me?'” The entire week those and other thoughts, sensible and nonsensical would dance through my head.

Finally, Saturday night, date night had arrived. I made sure to arrive early to gain my composure and to find a good parking spot I didn't have to pay for. (That leaves me with more disposable income for the date. I tend to focus on the details.)

Once there, I read that received a text message from my date. She was going to be a little late. This relieved me in a way. In fact, I probably would have been happy if she would had to postpone -- that's how nervous I was. But shortly she would arrive, and I'm glad she did. She greeted me with a big smile.

My first thought was, “God you're even prettier in person.”

After we exchanged pleasantries, we were off on our date. What happened next is to be continued...