Men's Dating Horror Stories, Vol. 2

In Volume 1 of Men's Dating Horror Stories, we encountered swingers, homeless Tinder users, and uncomfortably obsessive dog owners. In Volume 2, we're dealing with drugs, mothers, and guns? Hold on to your crotch.


After me and my long-term girlfriend broke up, I decided to give Tinder a try. I matched with a girl who seemed normal and nice, so we decided to meet for dinner. When I arrived, she was already completely shit faced and looked like she had been drinking for days. She then proceeded to do a line of coke off the dinner table. So, I just got up and left. 

emma's reaction: I'm honestly so proud of this dude for having enough wits about him to immediately exit the shit-tuation (see what I did there?). What a shitty first date to experience fresh out of a relationship. Really puts things into perspective, huh?


Soon after venturing into online dating, I met Mary. She was interesting and easy to talk to. She recommended we meet for the first time at a restaurant with "great reviews." It was not that "great" of a place but despite her questionable meal choice, we had a good enough time and agreed to meet up the following week at a local festival which I was going to with friends. The day of the festival, we had a pretty good time together, but I realized I wasn't really feeling it and this probably wasn't going to be long-term.

I waited a few days then, later that week, told Mary my feelings. I was as honest as I could be, saying that while I wasn't interested in her romantically, she was fun to spend time with and I'd like to be friends. I figured being straightforward was the way to go as to avoid any mixed messages. She was upset but understood — or so I thought. I was impressed at how maturely the conversation had gone and figured that was that. I was wrong.

A few days later, I was awoken very early on a Sunday morning by a knock on the door of my apartment. I was confused and half asleep, but figured it was a package delivery so answered it. You can imagine my surprise seeing Mary's MOTHER at the door. Taken aback and completely in shock, I let her in with no idea as to why she was there. She started to cry — no weep — about the demise of Mary and I's (very) brief relationship. I was completely stunned and had no idea what to say. She repeatedly kept asking me why I couldn't date Mary anymore and begged me to reconsider my decision. I said I was sorry but I did not see a future with her daughter but did she want some tea? I honestly had no idea how to console her. Or if I should? The whole thing was confusing and bizarre, but she finally left and I was ready to forget it ever happened. 

But of course, Mary reached out to me a couple weeks later. She asked to meet up because "she needed to talk to me about something." I was hesitant to agree, but figured it would be brief so we met at a nearby coffee shop. She told me she knew her mom had come by to talk to me, and she was so sorry and extremely embarrassed about the whole thing. Once we had talked through it, she asked if I wanted to start seeing each other again?!!? Again, I had to say no — that I wasn't interested in a relationship with her (OR her mom). We said our good-byes and thank God, this time it was really over.

emma's reaction: ... WHAT. I don't even. WHAT? I feel like you're leaving out a crucial piece of information or this mom/daughter duo is even more involved than me and Ellen (which is a FEAT). Ellen's gotten pissed before and fantasized about calling up men who've wronged me and giving them a piece of her incredibly vivid, biting mind, but she's never actually done it. But this mom DID it. I don't know if I'm horrified or impressed (JK, I'm 100% horrified).


Before I start, I wanted to add a few caveats. I’ve read Emma’s blog for a while. I’m a male in my early 30s, and I've dated a decent amount for the last decade or so. I have talked about this subject with friends, and I have witnessed the struggle, on both sides and in many forms, and I have to say: Women have it so much worse. 

There is really no comparison here. Sure, guys might go on some boring, terrible first dates sometime. You might stumble into a cheater. You might end up dating a girl with dad issues (fuck it, I said it). But overall, the magnitude in which guys fuck over girls and do stupid shit on dates (and more importantly, in relationships) is so much higher to the inverse situation that it is not worth comparing. Not that anybody is comparing, of course, but if the subject here is men venting about bad dating situations, we should first know this: Tough shit, guys. We have no biological clock. We live in a patriarchal society. Nobody cares about our stories. 

But still, here's my story.

A few years ago, I stumbled onto this familiar face on Tinder. I don’t want to say Tinder was new at this point; I don’t think it was. But it was a different era. More hookups, perhaps. But overall, it seemed less scummy. 

In this case, the girl had gone to my high school but graduated like three years before I did. I think I was probably around 27 or 28 at the time. She was like 30. She was also divorced. But she had been a collegiate volleyball player, and she had known my older sister, and she was very persistent and upfront after we matched. So I was like: Fuck it, sure, let’s meet up for a drink sometime. 

She lived in the suburbs (huge red flag!). I lived closer to downtown. But I was trying to be nice and we were meeting up on like a Tuesday or Wednesday, so I was trying to be flexible. She suggested a fairly stereotypical suburban sports bar chain, not far from where I grew up. This was a little unnerving. Not to sound snobby, but c’mon! It wasn't Buffalo Wild Wings. But not much better. 

Still, she was fitting in the meetup after a volleyball league, so I figured we’d meet, get a quick drink, talk a bit and see if an actual date would be worth it. What’s the harm? .  

So, I arrive on time-ish and she texts to say that she’ll be 15 minutes late. No worries, I’m always late. I order a drink. She arrives a few minutes later, and I ask if I can get her a drink. And she says three words that always shake me to my core: 

"I don’t drink."

OK. This is a tough spot for someone. I get it. We should all probably drink a little less. Maybe she’s a raging alcoholic. I'm sympathetic to that. There are many possible scenarios. And being a non-drinker in your early 30s while trying to date is probably very shitty. 

But I feel like this might be something to be discussed when you make plans for a meet-up at a bar. 

(A brief aside: I feel like I’ve started suggesting coffee places for first dates to accommodate this scenario. But still. C’mon.) 

So she gets a water and we go to sit down. But before we even sit down, she gets a text from a volleyball teammate who had just been at her practice or game or whatever. Her car has broken down, and she needs a jump. The girl is super nice about it and feels bad. But she needs to go help her friend. It’s going to take like 20 minutes. 

So I’m like: No worries, I’ll just come along. Better than just waiting here. So I down my drink. We hop in the car. And we go off to save this friend, all the while this girl is on her phone like she’s trying to navigate a ship across the Atlantic or something. Her friend is only like 8-10 minutes away. But it’s a fucking ordeal. And she keeps yelling into her phone at a strangely loud volume. 

So we finally find the girl on the side of a road in the suburbs. We jump the car.  It takes about 15 minutes or so. Another friend, this guy name Sergey, shows up and proceeds to help. Sergey seems super nice. But he appears really, really angry at what’s happening, like he’s bailed out this friend before. In a minute or two, he’s shouting, too. Very loudly. He appears to know what’s wrong with the car. And he thinks he can fix it himself if she'll follow him to Wal-Mart or something. Sergey seems like a real MacGyver type. All the while, I’m standing off to the side like, ‘Ooooooook.’ 

So, the friend thinks the car will get home. She’ll fix it in the morning, she says. So we hop back in the car and head back toward the bar. But no. Two minutes later, the friend calls again. Her car has stalled, this time on the side of a rather major highway. 

We speed off to help the friend for a second time. 

And here’s where things really start to go off the rails: Because we had driven back toward the bar, and because my “date” ends up taking a few wrong turns, we end up getting on the highway at a different point a few miles away. So we’re actually driving the opposite way the friend was, and we’re going to pass her going the other way. But instead of just exiting and getting back on the highway that way, my date pulls this super aggressive U-turn, hopping across a grass median in the process and then proceeds to pull a second U-turn (in the middle of the highway!) parking her car the wrong way on the shoulder, so the front of her car is facing the front of her friend’s car. 

You follow this? 

In my mind, I’m like: "Holy shit, that was a fucking ballsy maneuver, and not really in a good way." Moments later, Sergey shows up. At this point, I realize he does not have on shoes. 

Wait, did he ever have shoes? Who can say? 

We jump the car a second time. It takes, like, another 25 minutes. And shit is getting dramatic. There's more yelling. 

By the end, this whole ordeal has taken close to an hour and I’m spent. My date is apologetic enough. I feel bad, too. And I say the typical thing: Don’t worry about it. We needed to help out your friend. It’s not a big deal at all. I wouldn’t be doing anything interesting right now anyway. 

At this point, I guess I’m not totally opposed to a second meetup. Maybe this friend is just helpless? And I kind of feel for her. 

So we drive back to the bar, where she’s going to drop me back at my car. And then it happens.

As she parks next to my car, she goes: “By the way, I wanted to show you something. Do you like guns?” 

Good question! I suppose I don’t have anything specifically against guns. I would never own one, and I’ve never been hunting. But mostly, I’ve never heard a date say that. 

“Uhh, yeah, I guess,” I stammer. 

“Here, let me show you,” she says. 

So she reaches across me, opens the glove box, and pulls out a rather sleek-looking pistol. Again, I know nothing about guns. This one is small. But it looks very nice, I must admit. 

She tells me what kind of brand it is and asks if I want to hold it. 

So for a moment, I sit there, in the parking lot of a suburban sports bar chain, on a first date with a random Tinder match, holding a gun in the passenger seat.

After about five seconds, I offer the gun back. 

“Here,” I say, in probably the lamest voice that has ever come out of my mouth. 

Moments later, I decide it's time to leave. 

“Thank you so much,” I say. “I had a great time.” 

emma's reaction: I've never been more excited to use this line, but you quite literally dodged a bullet, sir. Also, not knowing whether or not Sergey ever had on shoes will haunt me for the rest of my days.

So, what did we learn?

1: Just because someone looks nice, doesn't mean they don't do coke.

2: No one delivers on Sunday, unless it's Amazon. Check your peephole first.

3: Always try and work alcohol into the conversation before you agree to a date, and riding in cars with girls is almost as dangerous as riding in cars with boys.

See you next time, gents.