Top 10 Dating Horror Stories from the Grid

By GOTG Staff Writers & Reader Submissions

Have you ever felt like your life is the beginning of a rom-com that keeps playing on repeat? And somehow skips over the part where the soft music plays and the perfectly coiffed yet delightfully rugged and charming man appears from under your nose to live happily ever after with?  

Have you ever started questioning the mistakes you made when you were younger because there must be some reason you’ve been “left behind” in this dating rapture purgatory?

Have you ever just had a date SO BAD that you thought they must have brought back Candid Camera just to mess with you?   


In honor of Valentine’s Day, the celebration of love and Hallmark, we asked our readers to give us THEIR WORST dating stories.  Whether you’re single and looking to mingle, or happily snuggling next to the love of your life – we know you’ll get a kick out of these because regardless of your situation today….well, we’ve all been there at some point.

We give you…



1) Poorly Timed Timeshare (Submitted by Chantel E.)

I went out with a guy that I wasn’t at all attracted to but was hilarious. The first date was short but it went well – he was so funny and sweet and those qualities trump “hot” any day for me. So a second date was set.

Dun Dun Dunnnnn…. I was picked up in his Jeep and he had a “surprise” location set.. so far so good – dude is spontaneous. We pull up to a community center type building and walk inside. A woman escorts us into a room with like forty other people sitting in chairs facing a host. We sit down and then, for over an hour we are pitched Lake Tahoe timeshares! I didn’t know what to do and when it would end. I sat there frozen wondering what the hell was going on and since I was only twenty-one, I had never been to anything like it.

FINALLY the pitch stopped – my date and I were led into a small room where a woman began showing us figures and homes. I found my voice and said: “I just met this man and we are in ZERO position to buy a timeshare together…” 

“I just met this man and we are in ZERO position to buy a timeshare together”.

The sales lady must have thought I was being generally funny or resistant to spending thousands of dollars . She starts forecasting what OUR holidays will be like and how much fun OUR future children will have in OUR LOVELY TAHOE TIMESHARE. I sat there completely baffled and glaring at this guy that somehow thought this was fun. I searched his face for some sort of teasing practical joke that maybe might make the whole thing hilarious – nope. He looked interested!

Finally the sales woman could see my irritation and started to understand that I really did not know this person all that well and after another hour told us we could “go claim our prize”. We had a choice; a plastic “digital camera” that required a cd to operate OR a beach umbrella. Three hours of sales and these are the rewards. My date looked at me and said “Sweets, pick what you want – doesn’t that camera look awesome!” He handed it to me (I wanted the umbrella) and we left.

Once back in his Jeep I asked what the hell all that was and he casually said “I thought we would get you a free digital camera!” He was apparently pumped on the whole thing. So next time you think your guy is being cheap just remember …it could be worse.


2) Would You Rather? (Submitted by Anonymous)

I once went on a date with a guy and he asked if I’d ever played the “would you rather game”.  It sounded like a good icebreaker so I agreed to do it.  His first question was, “Would you rather swim in a swimming pool of period blood or seamen?”  I think he regretted it instantly, but the date ended soon after.  

3) British Humor (Submitted by Laine H.)

I met this man at a bar on the Grid.  He was handsome, in law school, and BRITISH– which is as easy to find in Sacramento as a unicorn.  I assumed after being a venus flytrap for weirdos over the past year, God was throwing me a bone.  

We quickly became inseparable doing brunch, dinner, and getting second (ok third  – did I mention the accent?) base intimate over some on-demand.  I was skeptical that he was in law school (he didn’t seem very bright and continually used the letter “U” in place of “you” in every text), but I was willing to look past it because he was handsome and I liked the way he said my name.  

Then one day I kept seeing the dreaded “…” appearing and reappearing on my screen, followed by the devastating confession – “I’m not British.”  Though I appreciated his offer to keep up the fake accent, I knew we’d never work out.  Now that I knew he was American, I expected a full grasp of the English language.  


4) First Impressions (Submitted by Kirsten S.)

I met this guy online and we decided to meet for the first time at a local restaurant. When I pulled up I knew it wasn’t going to work out because he had clumped cherry Chap Stick all over his lips and around his mouth. Not a great first impression.

We had dinner and he asked about my time in college. As I was telling him about my major he cut me off, took a BIC pen from his pocket and slapped it on the counter.

As I was telling him about my major he cut me off, took a BIC pen from his pocket and slapped it on the counter. 

“I make these wooden pens in my spare time.” He said.
“But this one is made of plastic and says BIC on it.” I responded.
He looked crushed that I noticed.  “Well, I make pens just like these.” He said.

The rest of the dinner was quiet and I left quickly after.


5) Vacation from Hell (Submitted by Anonymous)

I had been dating this guy and living with him for well over a year and he suggested we take a romantic vacation to Mexico.  Within days of arrival, he had all but abandoned me and had only come back to our room twice before confessing to me that he had cheated on me three times since arriving here.  After he walked out, I realized he had taken my passport and money and angrily reached out to him.  He then demanded I pay him $3,000 to get it back.  Realizing I was soon to be stranded in Mexico, I reached out to the hotel who helped corner him and get back my passport and money.  Needless to say, we broke up. 

6) Ride Hard or Ride Home (Submitted by Cyclers Anonymous)

Once I went on a date with a cycling enthusiast. On our first date, he offered to take me to dinner, but the catch was we were going to bike to dinner. To give some context, at that time I hadn’t been on a bike in at least five years…”rusty” is an understatement of my then cycling skills. He had an old cruiser style bicycle that he brought out of his garage for me to use.

Him? He clipped in to his pricey road bike to ride a mere two and a half miles to the restaurant. In the first few minutes of cruising through the residential part of East Sacramento, I fell off the bike. Almost scrapping the cruiser, I was able to catch myself and the bike without hitting the pavement. I’m not sure if I was more humiliated by my own lack of grace, or him commenting that I was a liability.

I’m not sure if I was more humiliated by my own lack of grace, or him commenting that I was a liability.

We got up to the intersection of Alhambra and H Street, busy as always, and there he goes. Feet still clipped to his pedals, he hit the pavement at the middle of this intersection. While he struggled to unclip while on the ground, I got off my bike and tried to help. He refused my help, which just made matters worse. The date, his bike, and his ego were not salvaged.

7) No Brunch for You (Submitted by Anonymous)

I went to my friend’s annual “Not Your Typical Easter Party” – which was essentially an excuse for everyone to dress up in pastels and get obliterated.  I met a cute guy and made some less than PG decisions.  For whatever reason, he had booked a hotel for the night so we went there.  

In the morning, his friend, whom he’d given a key to, burst into our room while we were sleeping asking if my new man friend would like to have brunch.  (I was pretty starving so I thought that sounded like a great idea.  Of course, I had assumed I’d be invited).  Faster than you could say French toast, both guys were out the door for brunch – leaving my stranded in a hotel where my friends had to pick me up.

Years later, they still send me “No brunch for you” memes of French toast.    


8) Can I At Least See It? (Submitted by Anonymous)

Several years ago I met a handsome guy at a bar and he asked me to go out.  We went to dinner, it went well, we shared a peck on the lips, and he asked me if I’d go out with him again a few days later to a work party.  The party was kind of far away, but he said he would drive and had a guest bedroom I could stay in.  The day of, he told me to dress in cocktail apparel so I wore a little black dress and hopped in his car.

When I got to the party, I found out that it was a BLACK TIE work party at his boss’s house.  When the bosses daughter showed up, in what looked like a white wedding dress, I was also informed that she and my date just recently broke up after dating for FIVE YEARS.  I slowly began putting the pieces together and, as this was the days before Uber could whisk you home from uncomfortable situations, so I decided to drink away my uncomfortableness.  

After the party, we went back to his place and I curled up in the guest room well aware that I was in no way interested in him or any hanky panky.  He curled up next to me, but quickly got the hint.  Dejected, he sat up and asked me a question which to this day still haunts me…..

“Can I at least just SEE IT?”

“Can I at least just SEE IT?”

Hoping I had misheard or misunderstood what he said, I leaned up and asked him to clarify.  As his hand started to point, I stopped him in hopes that I could discourage any further mortification for either of us. Realizing the peep show wasn’t going to happen, he preceded to LITERALLY beg. Mildly flattered and utterly exhausted, I contemplated what my friends would say if I succumbed to his request so I could sleep.  In the end, I knew they’d never let me hear the end of it so I just gave him a weird look, walked into the bathroom, and called my girlfriend for a ride.    

The other day he tried to add me on Instagram, it looks like he follows a bunch of weird anime porn. Figures.  


9) Ordering In (Submitted by It’s not delivery. It’s DiGiorno)

Three good dates in to a new guy I had a misunderstanding with him. To make it up to him I invited him over to my house for a cozy Sunday night on the couch. I told him there would be dinner and Netflix. (We all know what that is code for.) He said that sounded sweet and he was in.

Sunday rolls around and I am a bit hung-over from a river float the day before. I call him up and ask if pizza would be ok since my energy level isn’t that high. He says sure and that he LOVES pizza. At 6:30 pm he calls and asks if he can bring anything. I say no, I have some wine and we can just order when he gets here. “Order?” He says incredulously “I thought you were going to make the pizza”. I laugh and say “oh no, hahaha…I’m super tired so didn’t feel like cooking, is that ok?”. Dude then says we can go out instead if I don’t want to cook and I say I’d like to keep things close to home since it was Sunday and I had a busy week ahead. He then proceeds to STAND ME UP because I didn’t make him pizza….I didn’t realize ordering pizza was a turn off.

I then proceeded to call my best friend and WE ordered pizza instead.

10) White Rabbit (Submitted by David Copperfield)

I accepted a date with a guy that fancied himself  a “magician”. He had a white rabbit in a hat tattooed on his forearm and he was real nice on the eyes. He asked me to pick him up (warning 1). He suggested we get drinks at The Old Tavern (warning 2). He had me sit on the opposite side of the bar as him and “wait a second” before I ordered my drink (warning 3). He starts talking to a few older gentlemen and breaks out a stack of cards – after a few rounds of tricks the older guys give him a few $1’s each for his fancy card work trickery. He walks over and orders us two Pabst (warning 4). This game went on for several rounds of Pabst and while all the warning signs were there that this weirdo was paying for our “date” with Magic trick tips he was hot and his game was strong.

this weirdo was paying for our “date” with Magic trick

Basically I am an idiot, and took his pretty ass home. It wasn’t the most romantic night of my life I don’t think, and at some point in the evening I stepped away into my bathroom. I couldn’t have been in there for very damn long but when I came out the dude had pulled a full Houdini and was gone AND in his vanishing act he had managed to take the hard drive out of my desk top computer. Who does that?! A Magician. A Magician does that. I never saw him (or my hard drive) again.

BONUS: I Didn’t See the Signs (Submitted by Man on the Grid)

“There was a woman I met on tinder.  We talked for a week.  Hit it off.  When she arrived for our date, I realized very quickly that she had neglected to mention to me that she was both deaf and mute. We sat at the bar texting.  I went on a second date, but after that moved on.  Sign language is hard.  But I couldn’t help wondering, who doesn’t mention those things?”


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  1. Anonymous says

    I went on a date with a guy I’d met online who seemed intelligent, funny, and kind. All of this changed as soon as I took off my coat as I sat down at the table. His expression changed from a pleasant smile to one of abject horror. He said, “judging from your pictures I thought you’d be pretty and sexy, but look how SKINNY you are!” I said, “and judging from our phone conversation I thought you’d be nice, but look how RUDE you are!”, and I left. (BTW, he was no prize pig himself in the looks department!). He even sent me an email the next day, telling me never to contact him again because he found my body so unattractive. I thought, ‘ohh, don’t worry!!!’

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