first date blunders

“Waiter, Check Please!”……Worst First Dates

We’ve all been there: first date blunders where you can’t make it through dinner and have to say,  “Waiter Check Please!” you get the hell out. Maybe you laugh or cry about it later, but at the moment you are so in shock your mouth is agape.

Or you think surely there must be a hidden video camera and any second John Quiñones will pop out from “What Would You Do?

First date blunders can be funny to share, God knows I’ve had a few of my own. When it comes to love, sometimes laughter is the best medicine. I might have thought people would know what not to do on a first date, but history has proven me wrong. My stories are all true because let’s face it, you can’t make this stuff up. I categorized them into my top 5

What Not to Do date stories:
1. Drunk Boxer: 

My sister set me up with a friend of a friend. Turns out the guy was a boxer who could drink like a fish. At the end of our date we ended up at a bar in downtown Chicago where I was the only woman, and I had to get his bartender friend Luky (yeah I know, his real name) to help me wrestle the car keys away from him. This was long before I could have Ubered myself out of the situation. When we finally got back in his car I found that the driver’s side window wouldn’t roll-up. It was the middle of winter and while driving us home on the freeway snow was blowing in sideways, blinding me. Thankfully I made it to my house and told the drunk boxer that he could sleep it off in his car.  The boxer was down for the count and I never had to throw a single punch!

2. Date Switch:

Halfway through a first date, I figured out the guy had some weird issues. While nice enough on the surface, he snapped at me at dinner and has an angry and possessive vibe. I tried to salvage the date (I know I was a codependent people pleaser) by begging my roommate to meet us for a drink. While I survived the date there was no way I would date him again. I said no politely that I wasn’t feeling it. No sooner than five minutes later he calls me back and said, “Hey if you don’t want to go out with me, what about your roommate, she seems nice!” OMG, hadn’t he seen the Seinfeld episode where Jerry and George try to do the roommate switch? Check it out. My roommate politely said ‘no’ to him as well, but the next day he phones her at the place where she worked to ask her again. Not only did the guy not know how to take NO for an answer he was a stalker too.

3. Cheap Date:

I went to dinner with a guy who ordered one of everything off the menu. When the check came, he said he didn’t have his credit card, so would I mind paying? I didn’t want to wash the dishes, so I paid. After dinner, he finds his ATM card in his pocket so he stops to get some cash but never pays me back. The Bank of Diane was closed after that.

4. Crab: 

I was set up for another blind date where the evening was going to be dinner and a show. On the way to the venue, I knew it was a mistake and was going to be a long night. But I said to myself how bad could a nice dinner be and comedy with George Carlin? The restaurant’s prix fixe dinner was king crab, (I’m deathly allergic to crab – I vomit in minutes) I ran to the bathroom, called my girlfriend, and asked, Should I eat the crab and end the date quickly or suffer through it? She convinced me surely my night would get better.  But my girlfriend was wrong. He spent the whole night never cracking a smile or a laugh; he never came out of his shell. I learned my lesson: never date a shellfish guy. Eat the crab instead!

5. Too much information: 

I was on a first date with a guy where I told him about a conversation I had just had with my girlfriends about plastic surgery. There was a TV show called Extreme Makeover, where if you win you get three plastic surgeries procedures done for free. Without disclosing what I would have chosen or without asking him, my date launches into his response. He says, First, I would fix my double chin (I hadn’t noticed that because he had a goatee). Second, I would get liposuction on my back ( I also hadn’t noticed that because he had a jacket on).  Third, I would have my ____ enlarged. To which the only appropriate response was- “Waiter, check, please!


People don’t go out on dinner dates anymore, so I get that this probably won’t happen to you. Dating should be fun, but dating blunders can also make for funny stories! We’ve all been there, share with me your best first date blunders, you’re amongst friends here. 

Back to Love Doc

All kinds of love and laughter,

18 thoughts on ““Waiter, Check Please!”……Worst First Dates”

    1. Diane Strachowski

      Thanks for the kind words. I’m hoping to do a post about dating goals and uncover my ‘Rule of Thirds’ when it comes to dating.
      Dr. Diane

  1. Diane,
    Funny stories, I can relate to your cheap guy. I was once on a date where before the check came, the guy said he had to go to the bathroom and never came back. I waited and when he didn’t return I was pissed. Not for the date ending but for getting stiffed, argh, men.
    thanks for all the advice,

    1. Diane Strachowski

      Yes, sounds like you felt the way I did, better to find out early about someone’s character. Better yet if a man is upfront and allows you to
      participate in the decision. Thanks for your comment,
      Dr. Diane

  2. Diane, love the stories! Let me share one of my own. On a first date in college, we went to dinner at an inexpensive restaurant near campus. At the next table there was a homeless person muttering to himself and stamping his feet. Poor fellow!

    Both of us didn’t know what to make of the situation so we blithely pretended the homeless guy wasn’t there. What an awkward start of the evening! Then after dinner he took me to a performance of Mozart’s The Magic Flute. More awkwardness given that I was into heavy metal music back then. Although, I think even he was bored!

    Ah, well, you just have to look back and laugh.

  3. I laughed out loud at these! I’m sure many girls have faced the same type of guys. I’ll add a few more:

    1. Gets too hands-y on the first date
    2. Is rude to the waiters/service staff
    3. Talks the entire time about himself or doesn’t talk at all!

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