What’s the worst date you’ve ever been on?


So, about five years ago, I started a novel that I’ve never finished.  It never got finished because other paying gigs came along over the years, and so I’d shelf the book to go make money so we could eat and all.  Anyway, I recently (read: yesterday) pulled my manuscript back out of the drawer because I could use a little no pressure creative push right now and have just arrived at a fun scene to write: a first date.  Now, this first date is going to be a good one because my poor girl’s life is going to fall apart the next day and the least I can do is give her a happy first date to remember in the midst of all the gloom and doom that’s coming.  Because I am just that nice of a make-believe puppeteer. But thinking about first dates has me thinking about bad first dates.  And I can’t help but ask– what was your worst first date? 

Since it’s only fair to answer what you ask, here is mine. 

I am somewhere in my early to mid twenties.  I’m a high school teacher, and a friend of mine wants to set me up with a guy she works with- who also works in a school (I will not give more details than that because although I cannot even remember this guy’s name or what he looked like (other than tall) for the life of me, I want to believe that he grew up to be a better man than what he demonstrated that night and because he might have, I’ll provide a protective layer of anonymity).  Sure, I say, because I happen to really trust this friend.  This guy and I make plans for dinner and meet at a restaurant.  As we’re talking- which seems to be going fine- the waitress comes up to take our drink orders.  She looks to be a few years younger than us.  And as she takes our orders, she chats us up.  Now, I can’t even remember what the conversation was about, but we certainly talked about more than our drink orders. 

When she walks off, my date looks at me and says- with not one lick of irony and a whole lot of self-importance- “I just hate it when the help talks to you.”  Excuse me?  Instantly repulsed, I managed to get out, “I used to be the help.”  Needless to say, we parted ways after dinner (I am not sure how I even managed to stay through the meal) and never spoke again. 

Alright, your turn.  Worst date ever?

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5 responses to “What’s the worst date you’ve ever been on?”

  1. Casey Hendrickson

    I was only 17 when my mom and her nurse friends set me up with this guy that worked with them. It was Thanksgiving day, and he took me out to this very nice restaurant. All he did all night was talk about how wonderful and rich he was, and how I should go to the beach with him (he even called my mom to beg her!!), but then asked if I had a gay friend for his “cousin”… I knew better, and found out after this whole ordeal that he was gay, and just looking for a partner.

  2. Stephanie

    Oh, Rosie, that’s NOTHING! One of my clients when I was practicing law in Charleston wanted to set me up with a guy from the Yacht Club. Back in my more material days, this sounded great. I knew he was divorced with kids, but that didn’t bother me. He shows up at my door on a summer Friday night, Volvo station wagon in my drive and a gin and tonic in his hand, because he was in a rush and didn’t have time to drink it at home. Which turned out to be his mother’s house. He took me to Sonic and raved about the fact that the bill came to a perfect $11.11. He then proceeded to explain that he didn’t have a job because he used to work for his father-in-law and when the marriage ended, so did the job (this was 2001, so not like jobs were as scarce like now). He was going to get his real estate license, but sailing season started, so he figured that he would just start in the fall. After complaining about his ex-wife and her new husband (so he had clearly been jobless long before sailing season started), he drove me by the house that they had lived in, just so I could see it. We ended the date then.

    I didn’t go out with him again.

  3. lulu hawke

    my worst date wasnt evrn my date it was my dad. I was 17 and dating a coworker. This guy was so sweet, responsible, but older than me. So he invited me to a halloween party at a mutual friends house. Coming from a mexican family I had to ask for permission to date adn my date had to come in and meet the family even thought it was our first date and they knew we worked together. anywho we did all that and then when we were getting ready to leave my house for the party my DAD says “okay so do you want me to follow you or go in the car with u?” Omg I about died, my date Jack was shocked he said “How bout u follow us” So my dad and parked in front of the house we were at. Jack was so cool about it. We still about talk about it!

  4. Maria Rivera

    I decided to go ahead & post this story here since Yvette is just DYING to hear about it!

    A coworker/friend mentioned that a new coworker (a lineman) wanted to take me out on a date. I had only talked with this guy a few times, but I thought he was good looking so I told him that I’d go out with him. The friend said he would join us with his girlfriend to make things less akward.

    The next night we meet up for our date at a local bar. First bad moment of the night was that my friend & his date didn’t show up. When I walked into the bar, I didn’t recognize my date at first because he was dressed like a thug. I had only seen him in his work uniform, so I didn’t know how he dressed outside of work. He was wearing baggy jeans, a black t-shirt with a long gold chain & what I call “gangster” Nike tennis shoes.
    Huge turnoff!! But, I knew I couldn’t just turn around & walk out, so I decided to make the best of it. We had a few drinks & he seemed ok. But then he kept drinking! Shot after shot of tequila! I could tell he was getting a little tipsy, so I suggested we go to dinner.

    As we were walking across the street to the restaurant, he tells me that he likes my long blonde hair. Before I could even say “thank you” he says, “Does the carpet match the drapes?” WTH?? Did he really just say that??? I politely told him that it was “none of his business” and also told him that if he made another remark like that, I was going to leave.

    We get to the restaurent & order steak & lobster. While we were waiting for our dinner, he tells me, “I think we should just skip dinner & go to my place.” When I asked him why, he replied, “So I can see you naked.” I was done! I walked out & left him sitting there.

    As soon as I left, I called my friend who bailed on us & chewed him out! Because he is a man, he found the whole thing to be hilarious. I was fuming!

    The next morning when I get to work, a waitress from the restaurant calls me. She said that my date didn’t have any money to pay the bill for our dinner. He gave her my name & told her to call me because I had said I would pay for it. I was beyond mad now! I told her to send me the bill and I would take care of it.

    Our company has a charge account with this restaurant. Our employees are allowed to charge meals there & then have the charges taken out of their paychecks. When I got the bill, I took it to my boss & told her what this guy had done to me a few days before. She charged the entire meal to the loser’s paycheck!

    It was the worst date ever, but I got the last laugh!

  5. Yvette

    lol Thank You Maria!! 😀 Lulu Ur dad was awesome.. totally something my mom would have done

    Mine **sigh** The One and only blind date if ever been on.. A Friend set me up with her co-worked bc I said I wouldnt go out with her and her BF alone anymore.. it was startin to feel like a 3some..lmao So I get a date.. We are the restuarant All chatting when I asked..

    Me: so what Do U when U arent working?
    Date: well when My kids mothers let me have them, we hang out at my moms house so she can help me with them
    Me: (looking back at my plate rolling my eyes bc I wasnt gonna get into that BS!) Umm ok, and when U dont get ur kids?
    Date: I hang out with my homies at the park
    Me: (thinking WTF? bc said park was a drug and gang hang out!!) what I said was.. Umm ok

    We had a few drinks at the bar bc I was not going anywhere else with Mr Homie.. on the ride home we at the stop light JUST be4 U get the entrance to my apt complex (U CAN SEE The APT!!) and I think to myself THANK GOD when what happens.. Whoop-whoop **FLASHING RED LIGHTS!** and i hear next to me “f*** I have a warrant”.. It turned out my friends tail light was out and he just let us go but Homie was sweating!! They drive me to my building and I tell them DONT even park just drop me off here! It wasnt even midnight..

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