Pick your favourite dating story

Well, the submissions are in and we have 7 competitors for the best dating horror story.

The best story, as voted by you will win its author a custom-made silver ring that I will be making in the coming weeks. (I will also be posting photos of the process as I make it!)

Posted below are the entries, please vote for your favourite on the poll on the top-right part of the blog (Yes RSS readers, I’m making you visit the actual page. The horror!) The winner will be selected on Saturday, September 19th. I’ll probably announce it on the Monday.

Without further ado:

Short Blind Date
by FB

This was in my last year of high school and I was just starting to dip my toe into the dating pool. Yeah, I know, late bloomer loser.

Anyway, my friend tells me I should just date anyone and everyone, and coincidentally, she happens to have a guy she can set me up with on a date.

I’m giving her this eye like “Anyone and Everyone huh?“.. and she reassures me that he’s a good person, who happens to be at the university I’m about to attend the following year. I’m thinking at the very least, I can get the scoop on what campus life is like, and what fast food joints & professors for first year classes to avoid.

So my friend gives my email address to the guy,… let’s call him Todd. Todd calls instead of emailing back (so far, so good).. and we plan to meet up for a Saturday night as a first dinner and a movie date thing. I press him for some details under the pretense that I would be able to spot him in a sea of guys on a random street corner, and he tells me he’s 5’10”, what he’ll be wearing and where he’ll be waiting at what time.

He picks some spot about an hour away from where I live, and it takes like 2 buses to get there. I’m thinking it’s like a special restaurant and the poor guy doesn’t have a car, and I didn’t want to embarrass him by asking if he could pick me up (and I didn’t have my license or a car at the time). So I take the hour to get to this area in the middle of nowhere.

The day comes, and I show up wearing this comfortable jersey red wrap dress and flip flops, with a low amount of makeup on. I get to the corner, and all I see is this sad little guy leaning up against the corner of the cafe wall. I am PRAYING that is not him, and since my dating karma was going to start off bad before it would get better, he waves and says “FB?

My heart falls, because I had some minimum expectations for the guy that clearly did not live up to what he said. I imagined him to have average looks, to be 5’10” and decently dressed for a first date.

No, no. The guy is in ripped jean shorts, a kind of dirty beer t-shirt, flip flops and he is 5’4′!!!!


He is a FULL 6 inches shorter than he said he’d be!!

The guy is SHORTER THAN ME. SHORTER THAN ME!!!!!!!!!!!!!!!

I’m about to bail at this point, but then my friend’s face pops in my head going: “FB, Anyone and Everyone. Dating pool virgin, here you go…” So I figure I’ll tough it out because heck, at least I’ll get a free dinner and some conversation to try out dating for the first time.

The first thing he says is : “Umm… you are.. really.. dressed up.
I’m thinking in my head: “… In a dress and flip flops? That’s being dressed up? We’re in trouble here.
So I reply: “Well, dressing up would be wearing heels, but I guess it was better I didn’t. *laughter to cover embarrassment*” Ohh zing.

He didn’t catch the zing.

Maybe he meant to say: 5 feet, ONE INCH. Instead of 5 feet, 10 inches. Anyway.

We start walking about 25 blocks or so and it was a good thing it was a nice night, because it was a longggg way. He leads me to the restaurant, and we pass a really nice sushi one (we had mentioned a shared love of sushi).. walks past the sushi restaurant and leads me into HOOTERS.

I’m walking in there, kind of annoyed at this point but still willing to see it to the end before I bail early. He tells me it’s his favourite restaurant, and I’m mentally stabbing my friend with a blunt pencil. We have an awkward, stilted conversation, because he confesses he isn’t actually in the university I’m about to go to. He’s at a different university, AFFILIATED with the one I am about to attend. We can’t even talk about school. The entire conversation was a blur, because I ate those wings to get out of there as soon as possible, and as I’m about to leave, he says he has his car and offers to give me a ride since we’re in the middle of nowhere-ish, and the public transit is another walk back. He also mentions it’s getting colder and I don’t have a sweater, so… it’d be better in the car.

I’m thinking: Okay.. not bad. That’s gentlemanly to offer to give me a ride home.

And the guy ends up driving me back the 25 blocks we walked, puts his flashers on and stops in front of the public transit station.

I’m.. confused. I thought he was giving me a ride back, and maybe he was just stopping at an area to pick up a friend or whatever. No. No. He tells me “I had a really great time meeting you, I think we really hit it off! Here’s the transit station……… you can get home okay by yourself right?

I’m… livid at this point but too polite as he is apparently my friend’s friend. I stutter something like: “Umm .. yeah. It was fun.” and I trudge into the transit station to ride home the hour it took me to get to HOOTERS to meet a loser.

The guy emails me the next day, asking if we can do it again. I politely told him I had other plans and I didn’t think we hit it off as a couple but we could be friends (yeah right).

He doesn’t get the hint from my “let’s be friends” email, presses my friend for details because he really thought he had an awesome time on the date (and so did I) and was hitting it off with me. When I told my friend what REALLY happened, she was mortified, but let him down easy telling him some made up story about how I was taking it slow because I was a dating virgin .. bla bla bla.

Awful. Luckily, some of the dates after that was better than that. I have another horror one where I am almost scared the guy was going to rape me, but that isn’t really funny. Just.. horrible and I’m glad I got out of there without getting hurt.

Animal Hospital Lover
by Revanche

Back in college, I worked at a local animal hospital. I’d run into all kinds of people who lived in my town from my past: a third grade teacher who totally recognized me 15 years later because I “hadn’t changed a bit,” the parents of a friend from second grade I hadn’t seen since the school district rezoned the elementary schools. Almost without exception, all the re-meet and greets were pleasant surprises, I was so happy to reconnect to these lovely folks!

One day, I made the mistake of thinking aloud, “[insert last name]? Hm, I went to school with a Boy Last-Name.”
“Oh??” said Boy’s mother.
“Well … until junior high, anyway …. ” stutter-stammered I. I hadn’t had any intention of remaking that particular one’s acquaintance.
“How interesting!” Boy’s mother.

Later that night, the phone rang. The phone AT WORK rang. “Is this R?”
“Er, why yes, I did just say my name. Can I help you?”
“This is Boy! My mom was just in there and told me she ran into you!”
“Er, why yes, yes she did. Is Fluffy ok?”
“So when do you get off work?”
“Notuntillate that’stheother line I’vegottago bye!”

Boy proceeded to phone-stalk me at work for the next two weeks. Then he took it to another level: he showed up at work! As the son of a good client and the top doc’s Favorite Boy Scout, he couldn’t just be shown the door. (ARGH) Even had to show him my work schedule to prove I couldn’t go to the school reunion-whatever thingie he kept inviting me to. And the other dinnery-groupish thing. Thank goodness for working nights, thank goodness for being Asian enough to claim curfew post-work shift!

He finally finagled his way into one weekday afternoon, asked me to do some nonsense like see a movie together or something. The number of times his invitations were declined had become embarrassing and I was still naive enough, new enough to dating (at age 19!) that I had no real idea how to deal efficiently and effectively with attention. Or any, for that matter.

As it turns out, he was pretty naive about dating as well. He picked me up. I chose the theatre. We arrived too late to catch the right movie, decided that there was another theatre across the road and started walking in that direction.

He pulled out his cell phone. And called his parents to check movie times at the other theatre. Across the freakin’ street!

I couldn’t believe it. I was floored, and totally done with the “date.” There was some waxing philosophical about swordfighting (a la Crouching Tiger, Hidden Dragon) on his part, there was much waxing Get-me-the-hell-HOME on mine. I pulled the “oh gosh, look at the time, I’ve got to get home since we’re not going to be at that movie!”

He continued to phone-stalk me for a few more weeks …..while I suddenly because much more deft at dodging his calls. :)

Vomit Boy
by Caroline

My story may not be the worst, but it’s definitely not good. Here goes:

I was home from college one weekend (this was years ago) and I decided to get my oil changed. I drove up to the local Jiffy Lube and the manager there started flirting with me. He also fixed one of the belts in my car for free. So (at the urging of my mother) I asked if there was anything I could do to thank him. He said that I could give him my number, which I did. I went back to school and after a few days passed I figured he must not have really been interested and just forgot about it. But he did call eventually (this should have been my first sign), and asked if I would come back up home for the St. Patrick’s Day weekend. He wanted to go out for St. Patrick’s Day. So we arranged a date. The day of, he calls and asks if I would mind picking him up, at his parents’ house (where he lives). Apparently he had a suspended driver’s license because he had been caught driving under the influence (should have been sign number 2). Then I hear him talking to someone in the background, and he tells me it’s his daughter. They both live at his parents’ house. Which is fine, I suppose. I mean, I’m only 21, so I’m not ready for kids, but this is just a date, so it’s fine.

So I agree that I will pick him up. Except he says it would be easier if I picked him up on the main street outside his parents’ subdivision. Ooooh-kay. I pick him up later that night at the parking lot of a dry-cleaners. We start off by going to a popular Irish pub in the area but it was so crowded that he couldn’t get fast enough service at the bar (sign number 3?) so we left. We went to a few other places, but they were all really busy (it was St. Patrick’s Day. On a Friday night. What did he expect?), so eventually we ended up at a Bennigan’s. (This is a now-defunct “Irish” version of a TGI Friday’s.) We get seated, and order some appetizers and some drinks.

By 10:30 he is trashed. So trashed in fact that he vomits. At the table. All over the table. The waiter immediately comes over with napkins and he and I try to clean up everything. My date just keeps demanding that the waiter bring him another drink. The waiter brings the check instead. In order to get us out of there, I pay the bill and escort my date to my car. It’s late enough that I can get away with saying that I need to go to sleep, so I start to drive him home. He passes out in my car. Eventually we get back to the area where I picked him up – but he won’t wake up. I don’t know where he lives. Eventually I call his house, and wake up his parents. My call goes something like this: “Hello? I’m SO sorry for calling and waking you up, but your son is passed out in my car and I don’t know where your house is. Can you give me directions?” But that’s not even the end! I get to his house, and his father comes outside to try and help get his semi-conscious son back into the house. At this point, my date wakes up, realizes he’s home, and thinks it’s time for the goodnight kiss. With vomit breath. As I pull away, his father has to pull him out of the car to keep him from grabbing and kissing me. Even his father apologized to me for his son’s behavior.

He never called me again.

Too Little, Too Late
By Frugal Fundamentals

I just got out of a ridiculously long term relationship and thought I should give dating a whirl again after 6 years. Enter Match.com. I fill in the details, upload a pic and think nothing more of it. Email after email floats in. I look at the prospective candidates, send a few emails and develop a repertoire with a guy Jeff, who’s about my age, incredibly well read, uses spell check and seems gainfully employed. We finally agree to meet for drinks at a place near my house.

The Date:
On the night of the date I obsessed over what to wear, selected just the right amount of jewelry and perfume and set out. He left it up to me to decide on a place so I picked a local bar/restaurant that wasn’t too far from me. I suggested we meet for drinks at 8pm and he was okay with that. Since I’m freakishly obsessive about being punctual I arrive at the place at 7:30pm. I sit in my car, heart racing and trying to resist the urge to gnaw on my freshly painted nails. 8:00pm rolls around and I do one last make up check, and walk one block down to the place. (I am grossly incapable of being fashionably late.) We had exchanged pictures so I had an idea of what to look for. (He looked gorgeous – tall, athletic, slim, well groomed…. YAY!) The bar was crowded as ever and I thought I would order a drink in the hope that he would see me… For the record, Im blind as a bat without my glasses and thought I would look better sans said specs that night. I order a sprite from the heavily tattooed yet gorgeous bartender and scouted the room for him. (I was too nervous to drink…)

8:10 pm rolls around…. no 6ft, blonde, blue eyed guy yet. I take a sip.
8:15pm More sprite. I begin to worry that I am drinking too much too fast and would need to pee soon.
8:30pm Now Im getting antsy, really, really antsy. A random too-drunk guy tries to initiate conversation… he smells of too much tequila and even more cigaretty smoke. I brush him off as politely as possible and whip out my cell phone to text “Jeff.”

Jeff texts me back saying that he’s at an Obama fundraiser and is running late. He asks if I mind waiting.

In my head Im thinking “WTF? Do I mind waiting….???? Has he figured out that I HAVE been waiting…for the last 1/2 hour?”

Trying to not be a grouchy and miserable date before the date even begins, I text him back saying that I could wait at most 15 minutes as I have an early morning. I set the timer on my cell phone. (I wish I were kidding about that but I am THAT crazy about people being late.) I engage in polite conversation with the bartender and order another sprite.

13 minutes later in walks the 6ft, blue eyed blonde Jeff. I was pleasantly surprised to see him in a business suit. He looked hell yummy…. 😛 (A little formal for the place I picked but hey, Im not complaining.) He sees me and comes over and hugs me. We go through the pleasantries of how nice it is to finally meet. He does not apologize for being late however. I try to get the bartenders attention and next thing I know, Jeff disappeared. He comes back a few minutes later and says “Yeah, I got us a table in the back.” Now I was annoyed. We were supposed to meet for drinks only. He shows up 43 minutes late and now I have to have dinner with him. We sit down, he grunts over the menu and is grossly impolite to our waitress. I try to make up by asking her how she is and giving her my order. (I’m now on my 3rd Sprite.) Jeff just ordered 2 beers (both for him) and was annoyed that I wasn’t drinking. I told him I was driving and didn’t feel like it. After calling me a lightweight he went on to comment on why I drove and didnt walk instead seeing that I lived in the neighborhood.

Okay, maybe he’s just had a long day and is absolutely starving. I try not to be judgemental and cut him some slack.

I make a joke about not wanting to walk in killer heels and he starts telling me how stupid it is to wear high heels in the first place.

At this point Im thinking, “Listen you f****er, I hate heels and hate dating… cut me some damn slack for trying to look good and be on time. Im debating my inner demons trying to figure out whether I should cut out on this date or at least be polite enough to finish dinner.

Thank God, our waitress comes back with our food and he shuts the hell up for a few minutes. For the record he orders the beef brisket with extra sauce and I order mussels in a wine broth. I offer him a some of my dish and he puts his saucy, beefy hands into the mussel pot to grab a few.

Somehow the idea of using a spoon never crossed his mind. More than that we had talked about how I dont eat meat so to have pieces of beef brisket swimming in my broth was nauseating at best. I stifle the need to hurl and eat some bread instead.

We start talking about work a few minutes later and he asks wayyy too many details about my job that have more to do with my clients than with what I do. He tells me about how passionate he is about politics and the starts asking me about my political affiliations. I try to be neutral on politics until I know a person well enough. I tell him that I feel all politicians are corrupt and it just comes down to picking the best of the worst really. He is clearly annoyed at my answer.

Now, I know Im no dating pro here but you do not start off a first date asking about politics and religion.

Next topic: He asks me where Im from and I tell him that I was born in S. Africa. He fiercely debates whether Im lying or not because according to him, Im not white enough, nor am I black enough to qualify. I firmly explained the history and demographic make up of S. Africa and he finally, grudgingly dropped the topic. I noticed the wine list on the table and casually asked him to tell me more about his favorite wines.. (we had briefly discusses whites versus reds over email.)

Now wine seems to be a safe topic to bring up. I like reds/whites and can hold a relatively knowledgeable conversation about the various grapes and regions.

Our waitress comes back to check in on us. She and I exchange a few pained glances and I secretly wonder if she would help me make my escape if he heads to the bathroom. (Hell, after 2 beers Im wondering how he could NOT want to pee. Half a glass into the soda and I was ready to explode.) He was incredibly knowledgeable about wine and I figured that our date may have gotten off to a rocky start but who knows, things might be looking up! Then he asks me which S. African wine I buy. I tell him. Then the shit hits the fan. He starts berating (and Im not kidding!) me for buying wines that were not socially responsible. He goes on and on about how the poor folks in S. Africa are underpaid for all the labor on the vineyards and I, as a so called South african, can not even do the decent thing and buy a bottle of wine to “give back to the community.” I didnt know what the hell to say. The restaurant is loud so his wild rants dont attract too much attention but our waitress is making frequent trips past our table. (I secretly think that she was standing by in case I needed to use her bottle opener as a weapon.) I try to explain that I didnt know about these wines and he cuts me off and says that maybe I should try to be a better person and give back a little.

At this point our waitress comes back to the table and offers us dessert. Before he could respond I cut him off, told her that I wasnt interested in dessert and if she could please bring me the bill. I think this shocked him. He looked a little taken aback and changed his tone. He tried to be nicer and less confrontational but at this point, I WAS DONE. He starts telling me about his little obsession with making lists. He tells me that the restaurant (along with the one next door) has been on his list for months. The waitress comes back, I grab cash from my purse, put it into the bill holder and grab my jacket. He doesnt offer to pay, he doesnt apologize for being a douche. Instead he says “you know, Im not an alcoholic or anything (this was his 4th beer in an hour) but do you want to go next door and grab a drink? Id like to cross this that place off my list.”

I look at him absolutely dumbfounded. Were we even AT the same table for the last hour? I said simply, “Jeff, I dont think this is for me. Please dont call me ever,” and hightailed the hell out of there! I should have told him that I wanted to cross him off my f*** list. I was shaking by the time I got into my car. I drove home, logged into match.com and deleted my account. It took me another 6 months before I went on another date….

Backstreet Boy
By Krystal

I had a crush on somebody I worked with in high school. When I moved to Michigan to go to University, he drove 3000 miles in a rusty truck to visit me. We went for a drive around the college campus. He pulled over beside this lake. It was all very romantic. He took my hands, stared into my eyes, and started singing “Shape of my Heart” by Backstreet Boys. It was so awkward and pretty much the cheesiest thing that I have ever had happen to me, so I couldn’t help but giggle. Then I couldn’t stop, and I was laughing so hard that I started crying. I thought it was a joke! He was absolutely mortified. He dropped my hands, drove me back to my dorm room, and immediately drove back home. I never heard from him again!

Okay I guess it wasn’t a horror story, but whenever I think of awkwardly cheesy moments in my dating history, that one always stays with me.

Is There a Problem, Officer?
by Lia

About four years ago, I and my boyfriend ( now become my husband ) went to celebrate our 2nd year anniversary.

After we had a romantic candle light dinner, we decided to back to our home. On the way before we arrived to my home, my boyfriend stopped his car in front of somebody’s house. The place was very empty and I just saw a few cars parked over there.

He tried to say something to me, he created a long long long story before he reached the main point ( to propose to me ). I just could not wait to hear that part, butttttttttttttttttttt……

Suddenly someone knocked the window, we were shocked… a police man! He asked my boyfriend what we were doing in here, and many kind of questions. I felt that he thought were a couple of robbers or criminals or something like that.

Hi Mom!
By Melanie

I met ‘S’ on an online dating site.
He seemed like an okay guy, although not really my type on a few different levels.
I had decided this year to be a little/lot more open-minded in my dating pursuits than I have been previously.
I first need to explain that I really dislike speaking on the phone prior to physically meeting people. I suppose it goes hand in hand with the fact that I don’t like to wait too long to meet men after striking up internet conversation.

Anyway, ‘S’ kept telling me how strange I was for disliking to talk on the phone.(This went on for a few email conversations) We arranged to meet and I sent along my phone number in case we had to reschedule, cancel, etc. Immediately after I sent him my number (and explaining that I did not like to speak on the phone previously)..he called. We chatted briefly (and awkwardly). He, still telling me how weird I was about the phone thing. He was obviously at some family event and was also talking with whomever was there. We reiterated plans to meet for drinks and a movie and hung up.
He called 5 minutes later to apologize for calling.

Fast forward to date night (after a few “good morning” texts…which would be nice in a long term relationship, but definitely weird in a non-dating ‘relationship’). We meet in front of the theatre at the same time and head over to the adjacent restaurant for a drink/quick bite.

We were seated next to a couple with two young children, the waiter (who was cute, go figure!) brought over some drinks and we started the process of getting to know each other. ‘S’ started telling me how popular he was in his musical career, knowing I worked in music as well. (I had never heard of him, but he works in the Christian gospel genre and I dealt more with mainstream pop/rock so that was understandable…ish) He kept on repeating how important he was and name dropping (which I totally HATE and refuse to take part in) and referring to himself in the third person.

I tried to change the topic to online dating and whether he had many online date experiences, etc. That was a big mistake. Immediately he jumped into raunchy stories of women he had dated (I don’t know how true it all was) and kept throwing around vulgar terms for womens private parts. LOUDLY. (All in front of these children!) I was mortified.

I have no clue why I agreed to continue with the rest of the date.

He insisted we see ‘Last House on the Left’. Which he said all his friends had raved about. I had seen reviews and was 100% not interested in, but knew how much he wanted to see it. We approach the ticket counter and he just stands there. Awkward pause between the ticket girl and he and I. I announce the movie to the girl, she prints the ticket and I wait for him to reach for his wallet. No reach. Awkward pause. I pull my wallet out and pay $25 for two tickets to a movie I don’t want to see.

We find our seats and the movie begins. We have had the discussion about annoying people talking while the movie is going on and how we both are not fans of that. 45 minutes into the movie and his phone rings. It rings about 4 times before he decides to answer it…IN THE THEATRE!!! He says he can’t talk and will call later. He sends a few texts and receives a few. By now we are the most hated people in the room.
With the movie over, we leave the theatre and attempt to say our goodbyes outside. He picks this moment to call his mother *yes, his mother* to tell her he is on the way home. I think ‘hmmmm…why doesn’t he wait until I am gone and he’s in his car?’

He is chatting up a storm with his mom and all of a sudden thrusts the phone onto my ear and says..“Say hi to my mother!” His mother and I briefly (and horribly awkwardly) say hello and I draw away from the phone.
WE say goodbye and head off to our cars. I get a phone call 20 minutes later (which I don’t answer) from him saying how successful our date was. He emails me and requests a second date. I politely decline saying I’m busy.

He still emails me randomly to this day to which I have sent simple one-liners out of courtesy.

That date was in April.

16 thoughts on “Pick your favourite dating story”

  1. All horrifying…and hilarious. My faves were the short, Hooters guy and Mr. Political.

    I'd also ignore e-mails from Mr. Hi Mom.

    After reading this, I have to say—don't be so freaking nice (obviously, some of these stories were when people were younger or new at this), but I've known "nice" girls who actually led guys on for months by never being available but still responding. Not that the guys in these stories don't deserve to be led on and left cold, but they won't know why (and won't learn) and it caused hassle for the girls too. Either ignore them completely or be firm that you're not and will never be interested.

  2. hahaha..thanks gals!
    Yeah, I have ignored the last few emails. The ones after the date I generally ended the email with:
    Good luck in your search! :)

  3. heh I think they're all pretty great!

    And I also wouldn't want to be a victim of any of those dates! *shudder*

    I do find that guys can be pretty dense though. For the ones that keep emailing, I just say that I'm not interested and leave it at that. It's plain and simple and they usually leave me alone after that.

    err…not that I've gone on dates with them, but sometimes after chatting online and I can tell they're tards.

  4. as a girl who's only dating experience involves dating someone for 7 years long distance, I am now very thankful after reading these dating experiences. O_O;;

    my favourite was the Short Blind Date & TOo Little, TOo Late. Yeesh! Talk about a bad date experience.

  5. LOVED reading these! You know I kept my email window open for like 3 hours trying to think of a good dating story but…I didn't date a lot. The guys I 'went with' weren't exactly "let's go on a date" material, hahah.

  6. I'm really wishing I hadn't missed the deadline because I have some doozies. Next time, Gadget! These all made me laugh. Mr. Politics…WOW!! And HOOTERS!? I love how they all seem to think everything has gone SO well!

  7. I agree that Melanie should not be emailing that guy back, one liners or not. He totally doesn't deserve it.

    These stories made me feel better about my own past dating life. I had so many stories, I couldn't think of which one to send in by the deadline. Sad! :) There are some truly appalling men out there!

  8. I don't even know what to say about these! If I had an experience like this I would crawl into a hole and never come out again! Well, maybe not but it would do enough damage to where I wouldn't consider dating for a while. I think the worst dating experiences come from the liars you find online. There are a lot of people who find success when trying to Start Love online, but when you have people registered who can't tell the truth to save their life- well, that's when you get stories like these!

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