In Honor Of Halloween, Readers Share Their Dating Horror Stories

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Forget ghosts, goblins and chainsaw murderers — the scariest thing most of us will actually encounter is the modern dating scene.

From the dreadful scrolling of dating apps to close encounters of the worst kind and the ghosting epidemic, dating can truly be a nightmare. It’s enough to make you scream — and not in a fun way.

So in honor of Halloween, I asked folks to send me their dating horror stories, the terrifying encounters that sent them running for the hills as if Michael Myers were on their tail. And what I heard certainly gave me a fright.

Dim the lights, lock the doors and bust out the treats (but skip the candy corn, you sick freaks). Prepare to be spooked!

This Tale From Samantha D. Will Make Your Skin Crawl:

I’d been chatting with a guy I met online for a couple of weeks, and we were finally meeting up for drinks for our first date. I really liked him so far, and I wanted to make a good first impression. I went to the salon for a blowout, spent extra time on my makeup and spent longer than I’d like to admit trying to pick out the perfect outfit.

I texted to let him know I was on my way, but he didn’t respond. I thought, “No big deal, he’s probably driving.”

When I got to the bar, I ordered two waters for the table and a glass of wine for myself. 20 minutes later, still no sign of him, so I texted again. Nothing. More time went by. I ordered another glass of wine because at this point I was just mad. I called him. Straight to voicemail.

Furious, I wrote out the longest, most scathing text imaginable. I called him all sorts of names, reamed him out for wasting my time, told him to go f*** himself. It was definitely the wine talking… or maybe just my repeated disappointment with dating, I don’t know. But after I hit send, I spent the rest of the evening seething and coming to terms with the fact that I was going to die alone. Dramatic much?

The next day, I finally got a text back from him… “My mom died, Samantha.”

HORRIFIED is an understatement. I was humiliated by my behavior and felt so awful. I sent him another long note… this time groveling and apologizing. But I never heard from him again. He blocked me.

This was two years ago. We could be planning our wedding right now if I wasn’t such an asshole.

Is Jake V. Husband Material?

First date, 7 minutes in, she opened her list of qualities she wanted in her future husband.

Amber:

Plot twist: Jake had all the qualities, and they are now married!

I’m just kidding, but that would have been funny.

Tom G. Meets The Parents:

Took a girl out to dinner once, and we really hit it off. She was sweet, we had a lot in common. It went so well we decided to walk to a bar a few blocks away for a nightcap after dinner.

When we got outside, she told me she needed to make a quick phone call. No problem. I waited while she stepped aside and pulled out her phone. I heard the FaceTime ringtone.

A few moments later, she’s walking towards me, points her phone at me and tells me to say hello. It was HER PARENTS. Not wanting to be rude, I awkwardly waved hello and just said “Hi, I’m Tom.” I looked at her to save me from this situation and she’s just smiling, holding the phone. After some small talk I don’t even remember, she told them goodbye and got off the phone.

She told me that it’s important for her parents to like the person she’s dating, so she likes to get the meeting out of the way early. And I wondered how many men she had done that to.

Nice girl. But no thanks.

Amber:

Apparently, this is actually a thing! One of my buddies went out with a girl a few years ago, and she picked the bar where they would go after dinner. When they got there, her parents AND sister were there. 

At first, he thought it was just a wild coincidence, but nope. She actually invited her family to come hang out on their first date to sort of “feel him out.” There was not a second date.

Anthony’s Date Vanished Without A Trace:

Picked a girl up for a third date, and I wrecked on the way to the restaurant. Not my fault, car pulled out right in front of me, but still a mood killer. While we were waiting for the police to arrive, she called her ex-boyfriend to pick her up.

Amber:

She was going to get that free meal one way or another, Anthony.

The Kiss Of Death With Aly B:

My “scariest” date was when I went out to lunch on New Year’s Day with a new guy.

A day or two before we went out, we were talking about our NYE plans. He was going to be working delivering pizzas. I was going to be at a family party. So neither of us were going to get a NYE kiss. So when I got to Noodles and Company for lunch on Jan. 1, he was ready. He met me at my car (which I didn’t like because I was putting the finishing touches on my lip gloss). When I stepped out, he planted a kiss on me — tongue and all! All I could do was laugh. My feet weren’t even planted yet. I fell over.

During lunch, he proceeded to tell me about a mouth infection he had recently which he “got from his ex-girlfriend.” Then he gave me details about how he had to take pills to produce saliva. (To this day I still have no idea what the infection was. Never heard of it before or after). Then he said “I really want to kiss you again.” To which I said NO.

I went home and looked for mouthwash to gargle but didn’t have any, so I grabbed my brother’s Skol vodka out of the cabinet and used that.

Thankfully, I did not get a mouth infection and I never saw him again.

Amber:

Ah, reminds me of college.

The Skol vodka, that is. Not the mouth infection. I can’t imagine the headache it would give me now, but $11 for a handle was a hell of a deal for a broke 19-year-old.

Randall B. But The ‘B’ Stands For Babysitter:

Met a woman on Tinder, and we decided to see a movie. She told me the movie had to be rated PG, and I thought she was joking until she showed up with her 5-year-old kid. Had the nerve to ask me to buy him popcorn, too.

Amber:

I would never shame a single mom who can’t find or afford a babysitter. But yeah, she should have communicated that ahead of time. Or at least had the decency to sneak in some snacks in her purse.

Thanks For Dinner, Gen X Warren, Gotta Ghost:

A couple of years before I met my wife, someone suggested I should give a dating website a try. Went out with a lady about three or four times, movie, drinks, dinner, etc. I started to realize that we really never went out on a Friday night or Saturday night, always a weeknight or Sunday afternoon. Then she said she would reach out to me when she wanted to go out again, and I never heard back. 

A little bit later, I told a friend of mine, and he said he found out that women were using dating apps and websites as a way to have different guys take them out, with no intention of ever dating. They just wanted free meals and entertainment. This is around 2012.

Amber:

I regret to inform you, Gen X Warren, that this sort of thing is still happening in the Year of Our Lord 2024.

Ashley’s Not-So-Happy Hour:

I went on a date, and she picked the place because her ex was a bartender there. Awkwarrrrd.

Amber:

Classic jealousy tactic. Sam Hunt has a song about this.

A One-Night Stand That Went Horribly, Horribly Wrong:

Several years ago, I met a woman at a party and ended up back at her apartment. We’d both been drinking, and she was basically throwing herself at me. So I figured I’d take the easy layup. (Don’t judge me, I’m a human man.) But I guess I didn’t realize just how much she had to drink.

So one thing led to another and we’re in her bed making out, clothes come off. I flipped her over on top of me and suddenly she PROJECTILE VOMITS all over my face and chest. It happened so fast, I didn’t even have time to close my mouth.

I threw her off of me because I was not trying to be a gentleman at this point, and I sprinted to the bathroom to throw up myself. I destroyed her bathroom looking for mouthwash (never found any) and jumped in the shower. That’s when I realized there was no towel. So I went back in the bedroom, soaking wet and dripping all over the floor, put on my pants and shoes (didn’t even stay long enough to find my shirt) and left. She was in the front room at that point and just yelled “sorry” as I high-tailed it out the door.

No more drunken one-night stands after that.

Amber:

I don’t have a Womansplaining trophy for the most horrifying dating story, Anonymous, but if I did, it would be all yours.

I immediately thought of that one Always Sunny episode where Charlie swallowed too many blood caplets.

But this actually does remind me of a true story from college. One of my roommates (we’ll call her Lisa) was notorious for getting too drunk and wetting her bed while she slept. One night (after a lot of $11 Skol vodka) she had a random hook-up sleeping over, and it happened.

In the morning, once Lisa realized she had peed herself, she snuck out of the bedroom and left the poor guy there — leading him to believe HE had pissed the bed.

I was standing in the kitchen drinking coffee as I watched the dude bolt through the living room and out of the apartment like a proverbial bat out of hell. He didn’t even say good morning!

Jessica T. Got A Jump Scare On Instagram:

I had been dating a man for 10 months (!!!), and I was crazy about him. Even started some low-key wedding planning with my girlfriends because I was SURE he was the one.

One day, I was scrolling my search page on Instagram when I saw a cute family, and the man looked a lot like my boyfriend. You can guess where this is going. It WAS my boyfriend. He was one of those “I don’t do social media” guys, but he was all over his wife’s page!

I got on the AWDTSG (Are We Dating The Same Guy) Facebook page for my city and found out he was doing this with MULTIPLE WOMEN! He had his own apartment and everything, none of us suspected a thing! I guess his wife thought he was traveling for work.

Amber:

I will never understand why people get married if this is how they are going to act. Plus, it just sounds exhausting. It takes a lot of effort and money to be that sneaky.

But I think it happens more than you think. I used to work with a woman whose husband was an employee of the U.S. Postal Service, and he was always supposedly in different cities for work. Having never heard of a traveling mailman, I was skeptical. But it was none of my business.

Turns out, he wasn’t on business trips at all. He was, of course, cheating, and my co-worker eventually caught on.

I imagine living a double life used to be easier before social media. Now, sooner or later, the algorithm is going to tell on you.

Speaking of…

Coming Up: Signs Your Partner Is Cheating

We’ll break down the tell-tale signs that your wife/husband/boyfriend/girlfriend is messing around behind your back. And I’ll share with you some (now funny) stories about a couple of numbnuts who fumbled me.

Have YOU ever been cheated on? How did you find out? Or maybe you were the unfaithful dirty dog! No judgment here, just email your stories to Amber.Harding@outkick.com. It’s about to get real Jerry Springer-ish (RIP) up in here next week!

One More Thing

In case those stories weren’t scary enough for you AND you’re looking to spice things up on Halloween night, here’s an idea:

Womansplaining is a weekly column about dating, marriage, sex and relationships.

Email your thoughts, questions, stories and gripes to Amber.Harding@OutKick.com or tweet her @TheAmberHarding.