What I Learned From Accidentally Going On A Date With A 40-Year-Old

Dating is hard. I think we can all agree this is a concrete fact of life.

Case in point: I ended up on a date with a 40-year-old.

How, you ask? Well, tequila mostly. And the experience made me realize a few things about dating.

20th Century Fo

I met this dude six tequila shots deep, about to embark upon the questionable path of number seven.

He was standing next to me at the bar. He heard me order tequila shots, and told the bartender to add an extra one for him.

I made some smartass remark about how it was rude to eavesdrop – original, I know– and probably made a comment about how much I loved the Drake song that was playing.

Through my tequila goggles, this guy was cute, well-dressed and funny. Plus, he liked tequila. We took our shot, laughed, exchanged numbers and agreed to meet up soon.

Fast forward to our date.

First of all, he texted me to make the plans... whatever.

I arrived at the bar where we were meeting and immediately realized he was not as cute as I had originally thought (thanks, tequila), and definitely older than me. However, I'm not a quitter, so I powered forward unfazed.

Also, he had tequila waiting for me. Well-played, sir.


He knew every bartender, and immediately started bragging about how he could get us free shots. I wasn't sad about it, but COME ON, dude.

Our conversation throughout the night consisted of three topics: alcohol, pizza and basketball.

These are all things I love, but not riveting. He mentioned he played basketball in college, so I immediately went to the bathroom and texted my friend all the details so she could stalk him. (Yes, guys, we all do this.)

After 10 minutes, my friend texted me to report her findings.

Piper, there was no one on the Maryland basketball team with his name from 2006 and up. He is lying.

Great. This could be going better. I start to steer the conversation back toward his time on the team, and asked him what years he played. He answered, “1995 to 1999.”


Just to clarify, I was born in 1992, which puts me at a whopping 3 years old when he started college. He literally graduated from college when I was in first grade.


I know age is just a number, but I immediately knew this 15-year age gap was not going to fly. I casually responded with, “Oh, I graduated from college in 2014,” and ordered another round of shots.

Then, I ate an entire pizza in front of him because I no longer cared what he thought.

I love situations like these because they make me feel like my life is a sitcom. Other than being a completely hilarious story to tell in the future, it made me realize a few things about dating:

1. Perpetually single people are just that: perpetually single.

I'm not saying this guy was a fuckboy, but I AM saying he had all the right signs: bragging about money, only texting to make plans, shallow conversation, etc.

These lovely characteristics are ones we all see in people in their 20s. But to see it from someone who's 40 made me realize people who act like this when they are young may not change... ie, this dude.

You have officially been warned.

2. The stereotypes about athletes can be true.

They don't call them stereotypes for nothing. As a former student athlete, I've had a lot of experience with other athletes.

A lot of my friends were athletes, and they are the best people I have ever met. Seriously: The most inspiring, incredible people I know are former or current athletes.

That being said, a lot of athletes are known to be players because people are constantly throwing themselves at them.

All of the bartenders were flirting with Mr. 40 while we were on a date.

3. Always say "yes" to dates.

Unless these people give you serial killer vibes, always say "yes" to dates. You never know: You might like the person.

Worst-case scenario, you will end up with a funny story. Dating helps us figure out what we do and don't want in the people we end up with.

For example, I now know I don't want to date a 40-year-old who only talks about alcohol and money. You have to figure out what flips your pancake and what ruffles your feathers.

4. Tequila brings people together.

Need I say more?