My First Date At 30 Years Old Was A Total Fail, But Here's Why I'm OK With It

Unlike the sequel to "How Stella Got Her Groove Back" that never was, you can never say Reggie Wade left his audience hanging.

Many people have asked for part two of this story. Well... like two people. But hey, if Kellyanne Conway and Sean Spicer can get away with “alternative facts,” so can I.

If you didn't read part one, here's a quick synopsis: I turned 30 years old, and had never been on a date. So, I went to a matchmaker, and she found a girl who agreed to go out with me.

That's the long and short of it. I left off with my date coming through the door, leaving me momentarily smitten. We exchanged some pleasantries and platitudes, and my exact thoughts were, “Wow, you're even prettier in person.”

We went for a short walk so we could get to know each other a little better. We started off with the casual stuff, and talked about birthdays and horoscopes.

Soon after, we decided to get something to eat. As we waited for our tacos, the subjects got even more personal. We spoke about our careers and what we wanted to do professionally, in the future.

Once our food was ready, we got into the meat and potatoes as the conversation turned to family. That was a fun conversation... especially with the eccentricities in my family.

After our dinner, she suggested dessert.

I was overjoyed... and not just because I love dessert. I had already planned to take her to this dessert place a few blocks away.

Everything was going according to plan. With every minute that passed, I got more comfortable. I started thinking to myself, “This dating stuff is cool. It's like talking and hanging out with a new friend.”

But a friend you eventually want to sleep with.

I couldn't believe how well it was going. Arriving at the dessert place was probably the peak of the date.

By this time, we were joking and laughing. Our conversation seemed natural, and there were none of the forced pleasantries that set the tone early on.

It looked like we were really enjoying each other's company.

At least, I knew I was. After that, we walked to my car and I drove her home.

Before the date, all these people and their mothers had informed me I had to give her a goodnight kiss. I went back and forth all night.

Should I do it? Is the vibe right?

I parked the car and walked up to her door. But when the moment came, I chickened out. I went for the hug instead.

I come from a long line of ladies' men, but I've always suspected the gene had skipped me. I just couldn't do it. I was scared. Maybe she didn't want to kiss me... or what if she had backed away? It would be so embarrassing.

We told each other we had had a great time, and she agreed to go on another date! Success. Or so I thought...

On the drive home, I was ecstatic: I had gone on my first date. Granted, it was something I should have done about 15 years prior, but at that moment, I didn't care. I was proud of myself.

The holidays were coming up, and both our schedules were busy. So, our second date was planned for more than two weeks away.

During that time, we texted each other. We had some nice exchanges. But then, messages started to go unanswered, and radio silence occurred.

I got no response for about a week. I feared I had been ghosted… and I guess I was.


When she finally texted me back, it was to inform me I was a wonderful guy and we had a lot in common, but she did not see the relationship going in a romantic direction.

I was crushed.

She asked if I would like to go out again as friends. I politely declined and wished her well.  And just like that, it was over: no second date, no nothing.

It was hard. Friends were stunned. Hell, I was stunned.

I generally felt like she was into me.

At that moment, I got a visit from two of my oldest friends: negativity and doubt. They'd been gone for a while, but they had come back as friends to counsel me in my moment of need.

They told me,

You thought she liked you? Of course she didn't like you. You idiot. How could she? You're fat, you're ugly, you're boring.

It was the same song and dance they'd been singing to me for years. As usual, I started to agree.

Then, some of my real friends – including my matchmaker, Caitlin – assured me things like this happen, and not for the reasons I had originally thought.

Remember how I told you I didn't go in for that goodnight kiss? That may have hurt me.

Not only did I not kiss her, I also didn't hold her hand or touch her lower back while we were walking through doors. Nothing. I was so worried about being a gentleman that I didn't make a move.

So, I may have put myself in the friend zone. After realizing this, I spent the next few days kicking myself.

I replayed every detail of the date in my mind, recalling all the times I had had the opportunity to make a move.

“She kept saying her hands were cold while we were walking… I should have held her hand!” Phrases like that danced through my head.

After a few weeks, I was finally at peace with my “one and done” date. My matchmaker Caitlin assured me she would find me another match, and that we would work together on making the next match a better one.

It's still tough to think about. But like they say, what doesn't kill you makes you stronger. I do feel I'm stronger because of this experience.

Whether it was true or not, for about a week and a half, I realized how it felt to have a girl like her... and it was AMAZING.

Like Method Man said, “Nothing makes a man feel better than a woman.” I remember the way she would smile when I thought about her, and the rush I would get whenever she would text me.

Even though it was simple stuff, it still felt amazing... and I will never forget that feeling. It was like a drug, and I wanted more of it.

So, that feeling is my motivation. It's what I carry in my mind and heart as I do whatever it takes to find the woman of my dreams.