The Hilariously Unfunny Date… LOL


Picture this, boys.

One of your buddies comes up to you and says: “Hey, you’re dating, right? I know a girl. You have to meet her.”

“Yeah?,” you say, interested. “What’s she like?”

“She’s great. One year younger than you. Dark hair. Dark eyes. Italian. Totally pretty. And get this—she’s a doctor. Just moved back home from Chicago.”

You’re totally in, right?!?! Gorgeous, brilliant doctor? Where do I sign up?

Well, if you’re me and you make horrible decisions, you sign up to do this on an online-dating site.

This girl and I had some email back and forth. Her overuse of “LOL” every few sentences should have been a giveaway. I mean, she wasn’t typing anything funny, LOL. She was just saying really normal things and because laughing is her favorite, she apparently just sat around laughing out loud as she typed to me, LOL.

On my second date in a dozen years, I met Gina. A doctor. A pretty one. A hearing-loss specialist.

Worst two and a half hours, ever.

This is the kind of stuff Jerry and George used to bitch about at the diner.

I’ve never been less attracted to a gorgeous doctor in my life. If you’d told me it was going to happen ahead of time, I wouldn’t have believed you.

We met at a decent Mexican restaurant because the pub we were planning to go to was overrun with Tuesday night lushes.

We ordered a pitcher of margaritas. It would prove to be insufficient, LOL.

I knew immediately this was going to suck. But I kept my cool and did my best to ask questions and feign interest in her responses.

Highlights of our evening included:

1. Gina’s favorite thing to do is laugh, she said. So she likes comedy clubs, LOL. This struck me as HILARIOUS because she was the least-funny person I had ever met.

2. Gina lived in Chicago for seven years. In those seven years, she had never once been to any of my favorite Windy City eateries. I asked her if she’d ever heard of Grant Achatz or his amazing restaurants—namely Alinea. I told her how amazing Alinea is supposed to be and how badly I want to get back to Chicago to eat there. I showed her the incredible food photography on Alinea’s website. She crinkled her nose and said: “Ohhh. This looks fancy. Is that, like, caviar? Yeah, I don’t think I could try that.” LOL.

3. Despite growing up in our area and living—I SHIT YOU NOT—three miles from the national park that we’re extremely fortunate to have nearby, Gina had never heard of it. Like, she didn’t know it was there. The park is more than 20,000 acres, for God’s sake.

Me: “Yeah, I really like to get out and go for long bike rides along the river on a Saturday or Sunday. That park is a total gem. Great place to escape. Do you like doing anything outdoors?”

Gina: “A little, I guess. Not really.”

I wish this margarita was stronger, I thought. Way stronger. LOL.

4. Mercifully, the waitress comes and I get to speak to someone interesting for 45 seconds. Gina orders some fajitas. She requests that the kitchen refrain from adding onions, mushrooms and roasted peppers to her dish, LOL.

OK, so she’s a picky eater. That’s not so bad. She’s a doctor. A really pretty one. Maybe I can get past this.

“I noticed you had tableside guacamole,” I told the waitress, glancing at Gina to make sure she was on board. “May we have some?”

The waitress walks away.

“Ooooh. I love fresh guacamole,” Gina said.

I about had a heart attack as this was the first time she’d exhibited competence in any one area of life, not counting school. LOL.

After another burst of aneurysm-inducing conversation about uninteresting things, the waitress came back to make the guacamole.

I politely let Gina choose the ingredients. I wanted her to choose how much of everything to put in the guacamole as she had previously demonstrated a propensity for pickiness.

Gina had the waitress double all the ingredients, LOL.

Double tomato. Double onion. Double garlic. Double jalapeño. Double lime juice.

Double fucking jalapeño!?!?!?!? That’s only smart if we’re trying to have a Who Will Have the Worst Diarrhea Contest tomorrow.

I didn’t say that out loud. Probably should have.

Needless to say, the guacamole tasted like absolute shit. She took three bites of it.

Time to take stock of this date.

The Gina Checklist:

  1. She’s the dumbest smart person I’ve ever met.
  2. Her favorite thing is laughing but she never does anything funny.
  3. Despite being beautiful, despite my tequila consumption and despite my prolonged against-my-will celibacy, I couldn’t be less interested in touching this girl.
  4. She is the destroyer of guacamole. The Guac Killer.

Signing for the check and walking out of the restaurant was one of the happiest moments of my entire life.

She hugged me in the parking lot and thanked me for dinner and drinks.

I had never been so happy to escape into the familiar confines of the Girlfriend Litmus Test. Before starting the car, I texted my neighbor Ryan to tell him what a shit festival of a date I’d just been on.

He laughed. He’s kind of a dick like that.

I texted her when I got home to thank her again for meeting me.

She said she wasn’t sure there was a romantic connection there (What could have ever given you that idea, Dr. Guac Killer?), but that she thought I was interesting and hoped I would show her some of my favorite trails in the national park sometime.


Online dating is bullshit.

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27 thoughts on “The Hilariously Unfunny Date… LOL

  1. jmyn says:

    Your blog is hilarious and raw! This post made me laugh out loud. Thanks!


  2. […] was The Hilariously Unfunny Date. I wanted to be dead almost the entire time I was with her. Imagine someone pulls into your […]


  3. trippyb says:

    Guac killing is unforgivable….
    I’ve been on more than one date where I was praying a suicide bomber would come into the restaurant….
    dating sucks


  4. […] when she tries to pull some stupid shit like doubling all the guacamole ingredients, I can step in and save the […]


  5. Just a Little Background Noise says:

    You need to have more dates!!!


    • Matt says:

      Yeah, I totally stopped doing that. I was desperate for dates early. Just trying to not be the pathetic single dumpee. But then one day I just… stopped.

      I haven’t been desperate for that attention anymore.

      It will happen when it’s supposed to, I figure.


  6. kerbey says:

    Picky eaters have something wrong in their brains. In her defense, perhaps if one spends eight years becoming a doctor, one has to replace commoner’s knowledge of local parks for things like big Latin words and degenerative diseases. Also (if that is her real name), I have never met an actual Gina. Gina to me is just the girl in Bon Jovi’s “Livin’ on a Prayer.” Your Gina is probably not familiar with it.


  7. […] went on a hilariously unfunny date. I wasn’t very nice when I wrote about her. I wish I’d been more kind. She did suck, […]


  8. I just laughed at your expense a lot. I’ve also tried and failed at online dating. My main problem is that I just don’t like many people. I’d rather sit around with all three of my friends and talk about Star Wars and music.


  9. zoumommy says:

    hilarious….sorry your experience sucked, but so glad I found your blog


  10. M. Safranski says:

    It takes a lot of frogs, that’s all I’ve learned so far. My first ever real online date several years ago was with a guy who ordered water at the restaurant (just water, nothing else, a glass of water), talked for two hours about his horrible divorce and bitchy ex-wife, then let me pay for my beer. Then, the kicker, said to me on the way out to our cars, “Well, I’m really impressed with you. I’d love to see you again.” That makes one of us, tool.

    LMAO at Jerry and George. I’m constantly telling people I feel like Elaine. And in real life, this shit just ain’t quite as funny.


  11. Beth Chara says:

    Hilarious!! I remember seeing your blog on my fb newsfeed a while ago in the summer – I’m glad I found you again! Funny, as always!


  12. Very funny, I have had my fair share of bad dates, ranging from boring to really worrying, thanks for sharing this, made me giggle angel cake.


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