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The gross, the creepy and the downright weird

The worst first dates ever

You meet a guy (or gal) and your blood hums and your stomach jitters. He’s funny, cute and available. He asks you out on a date. A first date. It’s going to be wonderful, magical…

But it isn’t.


First dates can be great but who wants to talk about those? Instead, let’s focus on bad first dates. You know the ones you want to forget but end up laughing about for the rest of your life.

I’m going to share some of my own colossal failures, huge goofs from friends, along with my favorites from the Internet.

A spark is extremely important in a romance but this is a bit much.

“It was my fourth date, he was stunning, we were still in that slightly awkward getting-to-know-each-other phase. We had a few wines at my place and it was going great! Things started to heat up, the fairy lights were on, candles and incense going, the works. I bent over seductively to grab a condom, his eyes were on me — and my hair caught fire. He screamed, I tried to play it off cool with an ‘oh happens all the time’ kind of laugh. It was so awkward we continued silently, the room absolutely reeked of burnt hair. Traumatic.”
-Felicity, 24 –

I never set myself on fire during a date, but I did have a very awkward moment.

I was home from college and a boy from high school wanted to get together for drinks. We’d both just turned twenty-one. He picked me up and we went to a bar. It was nice. We chatted and had a good time. We’d never dated in high school and I don’t think it was going to change with us in college. So, in a way, this wasn’t really a date (thank God!).

We walked out to his car. We’d each had one or maybe two beers so neither of us were drunk or even tipsy. He opened the passenger door for me and I went to step into the car. I was wearing long pants with these cute little flats. My foot hit a patch of ice and I literally slid under his car. I have no idea how I bent like that, but I did. I ended up lying in the parking lot with the bottom part of my body under his car and the top sticking out, staring up at him. I’ve never seen anyone laugh so hard. He kept trying to ask me if I were okay and help me up, but his laughter got in the way.

He did finally help me up but the poor guy laughed all the way home. He tried not to but just couldn’t stop. Lucky for him, I have a good sense of humor. We’re still friends today and this story does come up.


Here’s some advice. Don’t do any of these things if you want a second date.

“He was a dentist who spent the whole evening talking about himself and showing me pictures of his work. As the plates were being cleared he said, ‘Come on, your turn. Ask ME some questions!’”
-Ella, 27

I drove about 50 minutes to meet some guy from Tinder. When I got out of my car at the pub he had been waiting in the parking lot. The first words out of his mouth were “So wanna suck it?” NOT EVEN A HELLO! I didn’t say anything, got right back in my car and drive off. – gouramigirl” –

A friend of mine was dipping her toe into online dating. It never, ever went well. Sometimes, her stories were the only thing that got me into the office on Monday mornings.

She’d met a guy on one of the sites. They’d talked a bit and decided to meet up for afternoon drinks. He arrived late, wearing shorts, a T-shirt and carrying a backpack. The first words out of his mouth were, “You’re fatter than your picture.” Then, he proceeded to tell her that she needed to buy his drink because he didn’t have any money. She got up, told him that this wasn’t working for her and she started to leave. He said, “Wait. Where am I going to stay tonight?” She replied that she didn’t care but recommended his home. That wasn’t going to work for him. You see, he’d had his friend drive him over 70 miles and drop him off. Sure he was going to get lucky. He didn’t.

Think that’s bad? It gets worse.

This one made me laugh out loud.

“So I had just started dating this guy and we went out to a party because all of his friends were in town for the holidays. I had been sick for a couple of days but somehow decided this party was a good idea. Halfway through the night, the sudden urge to go to the restroom kicked in. I told my boyfriend to take me home ASAP. On the way out of the party he bumped into so many friends he hadn’t seen in a long time… I just waited in the car. On my way home things started to escalate, and yeah… five minutes away from my house it was too much too quick and very bad.. I pooped my pants in his car as I broke down in tears. We’ve been dating for five years now.”
-Valeria, 23

I don’t think I would’ve ever, EVER, been able to face that guy again.


In high school I had a crush on this boy named Joe. I was just learning to drink (and I don’t mean milk) and for me, that meant I puked every time I went out. This night was no different. I drank too much (probably a beer or two – I was a lightweight at the time. LOL) and got into those teen-angst-drama modes. I ran off on my own. Luckily, I had great friends. They came after me.

Now, I don’t tell many people this story because I do not come out looking good in any way, shape or form.

My friend chased and I continue to run (probably more like stumble). I remember looking over my shoulder at him and then—BAM! I ran straight into a tree. Face first. I fell. It wasn’t pretty. I had a black eye. (of course, I didn’t feel a thing at the time)

That would’ve been bad enough. Hell, it is bad enough, but I had to make it worse. I cried and told my friend to go away that I only wanted to see Joe. Poor Joe came and got me, carrying me back to the party so my friend could take me home. On the way back, I puked all over Joe.

Yep. Barfed on the boy I liked. That’s the way to get him to want to kiss you – NOT.

We did date for a while about a year or so later, but that’s the only good thing that happened.

Remember, I was in high school and that meant, I had to go home. My parents were not happy to see their drunk daughter with a black eye. My friend, chicken that he was, basically took me to the house and made sure I got inside before bailing (I don’t blame him). My mother called him to find out what really happened because she didn’t believe me. No one is drunk or stupid enough to run into a tree on foot. (Wrong. I was both. LOL).

I had to work at Kmart the next day. They made me stay in the back because of my black eye and I was hounded by caring friends to tell them the truth. No one believed that I truly ran into a tree.

School on Monday wasn’t any better. A few people hadn’t heard the story and one boy in particular kept pestering me to tell him what happened. He was going to beat up the guy who hit me (he was sooo sweet, but of course, I didn’t like him). I kept telling him that I didn’t want to because he’d laugh (and I was so over that reaction) and he kept insisting that he wouldn’t.

I told him.

He laughed. A lot.

Sigh. My teen years were not pretty.

But, at least I never had dates like these.

These border on the really strange.

“I went on a date with the literal boy next door thinking it would be sweet if not magical and fulfill all my teenage girlish dreams. When we went on the date, which was at a nature preserve, it was disappointingly awkward and we spent most of the time pulling twigs off of trees in silence. We ended up sitting on a log and talking and all of a sudden, when there was a lull in the conversation, he started leaning towards me and counting down OUT LOUD like he was a spaceship getting ready to say blastoff. He was actually counting down to kiss me! Needless to say, I whipped my head to look at him and say: ‘What are you doing?!?!!’ The date pretty much ended right there, but he still managed to work up the courage to try to make a few more moves on me before the evening ended.”
-Audrey, 20

“I went on a date with a guy whose idea of romance was taking me to his family’s church, where they were trying to break the record for a hymn-singing marathon. To clarify, the standing record was four hours. I thought we were going to a drive-in. ‘Oh, this’ll be so romantic and retro,’ I said. ‘This can’t possibly be an attempt at saving my soul,’ I said.” –

“During the conversation she started talking about a bunch of things I had an interest in, being quite specific. It eventually twigged that she must have checked my Instagram for stuff I liked/did. I figured this was fine since had we met on Tinder or something that’s pretty standard.

I went back to her place and her housemate looked shocked to see me, like, f**king terrified. When we had a moment alone she beckoned me into the hallway and showed me a picture, of me, that was circled in quite a violent fashion and asked me “Is this you?”

Then ensued the most terrifying argument I’ve seen between two women ever at which point I went full nope, left as quickly as physically possible, drove away and did not ask questions. I’m sorta hopeful that there was a reason for it all and it just came off as super weird, rather than the sinister explanation I’d assumed upon seeing it. – whitehousea”

I have a story that’s even stranger. It happened to a friend of mine. It wasn’t exactly a date but it’s too good not to tell.

My friend, Greg, and his wife, Tina have a business. At the time, they were renting a store in a small shopping center. An older couple owned the property. Tina became good friends with the wife (we’ll call her Annabelle and her husband Chuck).

At first, Annabelle would drop in occasionally to chat, and then it became daily, then several times a day. She started asking personal questions and bringing Tina small gifts. Tina was a tad annoyed but her and her husband just thought the older lady was lonely.

The landlords invited Greg and Tina to their house for dinner. When Greg and Tina arrived, the table was set–wine glasses, flower centerpiece, china and two dolls in chairs. These dolls looked just like Greg and Tina. As a matter of fact, Annabelle had made them so that Greg and Tina could be with her and Chuck always.

Yep. True story.

Greg and Tina are still alive but they did get out of that house and that shopping center.

So, I’ve shared my dating horror stories. I’d love to hear yours. Leave your comments below and let’s see who has the absolute worst date ever!!!


  1. Carolyn says:

    I was a 22-year-old sexually naive (I’d never had a date) determined virgin with a colleague/friend who was equally determined I was going to give it up. So she set me up with a friend of hers, a retired South American pro soccer player. Yes, he was THAT gorgeous and had a body that just wouldn’t quit.
    So we went for dinner to a fancy place and he pulled out all the stops – the nice wine, the long, panty-melting looks into my eyes, the feeding me little bites of dessert, buying me a rose and running it along my forearm, holding my hand and circling my palm with his thumb… all things designed to turn me into mush. And they worked. I was a sopping wet puddle of desire by the end of dinner. He then took me disco dancing (yes, this was in the Dark Ages 😄) and taught me all the standard moves (and a few of his own ‘special’ ones!). This man was full of moves.
    So we got back to my place and he walked me to the door. As soon as I turned around from unlocking the door to thank him for a lovely eveving he was all over me with kisses the likes of which I’d only ever read about in romance novels. He pushed me inside and headed for the couch, where he tried REALLY hard (pun intended) to punch my v-card. It was a very intense time that I still remember with embarrassment – because I kept saying, “No,” even though it felt SO good! I was a good girl, and good girls did not put out on the first date. Remember, this was a very long time ago!
    He made several efforts – very devastating efforts – and I was actually weakening when he asked if he could have a cup of coffee. I got up to make it and when I returned he was pretending to be asleep. So I covered him up with a blanket and went to bed, and sometime during the night he snuck out and left. I never saw him again.
    I kick myself now – he would have shown me a much better first-time than I actually had a few years later. I dont know how much ny friend paid him or what dirt she had on him, but it wasn’t enough for him to offer me a second try.

    1. Linda Odea says:

      Oh man, I haven’t been there exactly but I do wish I’d picked someone else for my first. Sounds like this guy would’ve been great. Wish you had a picture.

  2. Virginia says:

    Being an elementary school teacher you don’t get much of a chance to meet the opposite sex. I was young, newly divorced and lonely. A fellow teacher friend of mine offered to introduce me to an old friend of her husbands who had seen my picture and expressed an interest in meeting me. She and her husband was in my age bracket and very socially active so I figured why not? I agreed to the date. He showed up at my house on time. This is where a girl should have a peep hole in the door. I opened the door to a man twice my age if not more so. He actually wore dentures! I was stuck. We went to dinner then back to my house. He attempted to French kiss me even offered to remove his dentures if I preferred. I literally kept moving around the living room to keep away from him. I finally got him to leave after I repeatedly told him I had to go to mass immediately. The next day I mentioned to my co-worker about the “blind date” and extreme age difference. She was unfazed about it. Her comment was “I told you he was an old friend of my husband ” . I explained “old friend ” can have more than one meaning. Needless to say I never went out with the old friend again and my co-worker moved to another school. No loss for me. Never went on another blind date again.

    1. Linda Odea says:

      LOL. Sorry, but it is kind of funny – now.
      I would’ve assumed the same thing, that the guy was a similar age. Your friend was playing with semantics. Thank you, because I am now forewarned about “an old friend” and most certainly ask. LOL.

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