Datemares (vol. 1)

First, I asked men to send me their so-bad-it's-funny dating horror stories. Now, it's the ladies' turn, and we're calling their series Datemares. Welcome to our hell, boys. Grab the popcorn, settle in, and get ready for glances into the dating world from the female perspective that you never asked for but are getting anyway.


I dated a dude who cheated on me so, naturally, I kicked him to the curb. He kept emailing and calling me incessantly so I blocked him on LITERALLY EVERY CHANNEL I COULD THINK OF. But guess what? He found me on freakin' VENMO.  Yes. Dudebro tried to holla on VENMO by sending me $1 and a note saying he missed me. I accepted that dollar and then blocked him.

emma's reaction: You're my new best friend. I hope you spent that dollar on something really special – like a banana. Or an avocado. Or any other singular piece of fruit. 


A few years ago, I was recently single from a long term relationship (actually, we're technically still dating. For real. The last time he spoke to me was to say “I just need a break because med school is so hard," which wasn't a true breakup) and several of my friends kept trying to set me up with different guys. I finally agreed to go out with one of my co-worker’s brothers who suggested we go to dinner with his sister (who set us up) and her fiancé.

We went to a more expensive restaurant, meaning it was a true sit-down dinner — not a dine and dash. Within the first 10 minutes of sitting down, he asked me my stance on gun control and abortion. I was obviously pretty taken aback, but tried to roll with it by responding, “I think ladies should have a choice and love guns are the best kind of gun.” He was not amused, and told me to take it seriously because he was in law school and a decorated member of the Young Republicans club. After this exchange, I turned my focus toward his sister for the rest of the meal while he continuously sighed loudly every couple of minutes and complained about how long dinner was taking. At the end of the meal, he told his future brother-in-law to pick up the tab. Needless to say, I paid for my own shit and peaced out.

A few months later, I was at a gay club with a guy friend and that's when I saw it — the Young Republican was not only there but MAKING OUT WITH A DUDE ON THE DANCE FLOOR. All I could do was make awkward eye contact and point at him. He saw me, came over, and all he could say was, “Fuck. Don’t tell my sister.” I honored his request, but his pissy, over-compensating attitude on our date suddenly made a lot more sense.

emma's reaction: This is the most beautiful poetic justice I've ever read in my entire life. And, funnily enough, it's the not the first or even second time I've heard about a super right-wing conservative, prickish asshole turning out to be gay. So. Methinks there's something bigger going on there...


The year was 2016. I had just gotten out of a shit storm relationship with another Tinder nightmare (I’m talking micro-peen, embezzled $20k from his boss, cheated on me the entire time shit storm). I was being a player and swipin left on some San Francisco fuckboys, when one night I was out with my friend and swiped right on this guy we'll call Paul. We started messaging and,  right away, Paul came across as very attentive and responsive, plus we had the same interests. So, I gave him my number. 

One thing I did notice early on that I would now consider a red flag is the fact that if I didn’t text him back right away, he’d keep on going. He also continually sent me selfies and pictures of his family and everything he was doing throughout the day. Like the very next day after getting my number, I woke up at 7am to texts of pictures from his trip to the grocery store. I don't care how much I like you, I will never give a flying fuck what you're getting at the grocery store at any time of day.

It was President's Day weekend when Paul and I connected on Tinder. I was going to a tiki bar with my guy friend to celebrate have a Monday off. After telling Paul this, he basically demanded he be invited. I thought it was kinda pushy for one day of talking, but I obliged. 

Fast forward to when Paul shows up at the tiki bar AN HOUR EARLY. No lie. When we meet up, the first thing I notice is he lied about his height and is actually two inches shorter than me. Not a huge deal breaker, but why lie? My friend pays for our first round of drinks, and we get to talking. By we, I mean him. He immediately took over the conversation, talking about his ex in great detail and how fucked up she was. Super attractive, right? He's now on a roll, dropping that he’s unemployed and has only 20 bucks in his bank account. He then offers to buy me a drink and I say: “No that’s okay. You should really save your last 20. Sounds like you might need it.” The whole night he told us how he has turrets and is severely bipolar (and has been hospitalized for it) but refuses to take his medicine. 

Being someone who can't hide her facial expressions well, my face was going crazy. But, of course, he didn't notice.

At some point, he tells us he was a member of the 4H club and enjoys killing and skinning rabbits and some other creepy shit. After hearing that, I immediately made up some excuse about how I didn't actually have tomorrow off for President's Day and had to get home and get to bed. 

All three of us walk outside. Paul turns to me and says "Come with me to my car. I made you cookies." WTF??? He then tries to kiss me, and I promptly turn it into an awkward, one-armed side hug.

When I got home, he was still texting me and I was barely responding. He sent me some long text about how I shouldn’t let him have beer because he forgot he has a GLUTEN INTOLERANCE. HOW DO YOU FORGET?  I just stopped texting him back, but the entire next day he kept at it. The final creepy af straw that made me block his number entirely was the video he sent me of him sitting in his mother's van, just staring at the camera. Not posing. Not talking. Just staring.


Seven months later, my older sister had just gotten out of a relationship. Being newly single, she joined good ole' Tinder.

One day, after getting home from work, my sis tells me about this guy she's been talking to on Tinder. She tells me how cute and attentive he is and how he's always texting her. She even told my mom about him and my mom was saying how this guy is such a catch and she can’t understand how he’s still single . So, I'm like "show me a picture."


I lost it, telling my sister MY Paul story and showing her all the texts he had sent me. We realized he had sent both of us the same selfies and videos. 

Alas, my sister was dehydrated and kept talking to him! Thankfully, a week later, she tells me she had to block him because he was just too fucking creepy (YEAH, SIS. I KNOW. I TRIED TO TELL YOU). He apparently wouldn’t stop texting her and started telling her all about his therapy sessions, in detail. She blocked him on all forms of social media as well as his phone number. 

I kept using Tinder, though.

emma's reaction: How are you still alive and unskinned? No, really. In a way, I feel bad for Paul because he clearly has many an issue, but since he wasn't willing to take medicine or help himself, my sympathy only goes so far. I sort of wish you had kept and sent me the video of him sitting in his MOTHER'S VAN, just staring at the camera. But maybe not. I already have enough anxiety in my life — I hardly need another ounce.

So, what did we learn here today?

1: Venmo can be a dating app if you try hard enough and believe in yourself.

2: If you ever encounter an outspoken, gun-loving, extreme right wing conservative prick, he's probably gay.

3: Making cookies for someone on a first date is cool if they don't come from a van that more than likely has skinned rabbits stored in the back.

Send me your dating horror stories any time (emmasthing @ gmail), and I'll see you next time for more Datemares.