The failures of a self-proclaimed Tinder playboy

I’m a man of my word and, as such, this week I’ll take my ego down a notch and share some of my #TinderFails.

Something you should keep in mind when using Tinder, or any dating website, for that matter: Nobody bats 1.000. Much like baseball, if you bat over .300 on Tinder – in terms of getting dates from your messages – you’re one of the better players in the game.

I’d consider myself a Babe Ruth on Tinder (with better abs). He had a career average of .342. I have more like a .450 average and as that average would suggest, more times than not, I don’t get a hit.

So let’s just dive into some of these failures headfirst. We can start with the time I unknowingly Tinder-flirted with a transsexual.

It all started innocently enough: She looked like a model, so obviously I swiped right and we matched.

She quickly messaged me at 2 a.m. on a Sunday morning, which means only one thing: Sex.

After asking me for somewhat explicit details of my physique, she started asking me about my sexual habits and then told me how she wanted the rest of the night to go.

It soon became clear that she was a he. I had that quintessential Ace Ventura “Einhorn is Finkle” moment (look it up on YouTube if you’re unfamiliar).

Now I consider myself an adventurous guy, but this was one road I was not going to travel down.

To be fair, I showed her picture to a bunch of my friends and they all agreed that she was a bombshell.

Let’s move along.

More recently, I got a message from a very attractive blonde who lived on Long Island. She was very eager to tell me about herself and what she did. She also used proper grammar, which to a journalist like myself is an incredible turn on. Seriously, I’ll take grammar over fake boobs six times out of 10.

She also texted me … a lot. I was OK with it because she seemed sincere and it also seemed like a sure thing. So we arranged to meet up.

The day before our first date I sent her a message: “We still on for tomorrow night?”

I got no response.

The next day I waited until about 5 p.m. and messaged her again: “You coming in tonight?”

Again, no response.

A couple of days later I decided to try one more time: “What happened to you the other night?”


There’s really no excuse for blowing me off like that, especially since she was the one who instigated conversation after conversation, so I can only assume she was in some terrible accident and wasn’t able to send me a message.

If you couldn’t tell, it really got to me … even though that’s something I’ve done to women  dozens of times.

Then there was the time I had my heart broken by an off-the-boat Irish beauty queen. Let’s call her Emily (in honor of “Blurred Lines” smoke show Emily Ratajkowski).

We went out for a couple of drinks and Emily had me laughing the whole time. We decided we would go out again.

Before I continue, I told my mom that I had met a nice Irish girl and she got really excited. Mama Hogan asked me, “What does she do?”

“She’s a waitress at Hooters.”

My mom laughed and said, “No, seriously.”

And I responded, “No, seriously.”

My mom took a deep breath and just walked away. I think that was her way of telling me she disapproved, but I can never be sure.

Anyway, I waited a few days before reaching out to Emily again. When I did, I asked if she would be around again the following weekend.

Her response: “Who is this?”

My response: “Nobody important.”

She clearly didn’t enjoy our date as much as I did … and it hurt.

Those are just three examples that stand out on a laundry list of rejections that my time in the Tinder world has brought me.

As I’ve said in the past, I try to have as many lines in the water as possible. If a few fish don’t take the bait, that’s fine – eventually I’m going to catch a keeper.

Until then, I’ll keep fishing.