More Creeps: Another Online Dating Story

Last week I wrote about the craziest online dating story that I have and everyone seemed to eat that up! So far it’s my most-read post thus far in my blogging journey, and I guess I’m not surprised because the story is insane. Interested in hearing about the Creeper Snacks guy? Check it out here.

After I wrote about that online dating horror story, I made mention of another online dating story that’s a little bit more scary, little bit less funny. I had a few people reach out to me asking me to write about it, so here we go! Again, I’ll preface this by saying that I’ve been online dating on multiple sites on and off for the last two-ish years and I have met some really great guys via the interwebs. Sometimes you just have to get through a lotttttt (alotalotalotalotalotalotalotalotalotalotalot) of creeps in the meantime.


So after my first ever online dating story going horribly wrong, I’m surprised I even continued with online dating. In fact, my online dating journey (if you can call it that) has been on and off again for awhile because I honestly hate it so much. I think it’s awkward and the first date always makes me want to throw up. Unfortunately wanting to find someone sometimes outweighed the awkwardness of the websites, so I jumped back on.

The story  about this guy (we’ll call him Jim mostly because that’s his name and I’m pretending that it’s not HA) starts about the same as the rest. I don’t remember what site I was on, but this tall, athletic guy (check and check) started reaching out to me and we struck up conversation. After a few days of talking, I gave him my number and we decided to meet up in early January at a local coffee shop in Milwaukee. Unfortunately the day of our date it was super super SUPER cold outside, so when he offered to pick me up outside my apartment to drive me the five blocks instead of walking, I took him up on it even though it’s WAY against the rules to let a guy know where you live when you don’t know him. I thought because I was meeting him outside of the apartment, I was good.

Strike One, Jessie.

While this time, he looked exactly like his photos, our date was a complete dud. He was a good looking guy, but he was a complete bro and we had absolutely nothing to talk about. Our date lasted less than an hour and he dropped me off at my apartment. He never texted me, I never texted him, so I thought it was over. Right?


About three weeks after our date (and three weeks of not having any conversations via text, call, carrier pigeon, nothing), I was sitting on my couch in my new studio apartment on a Sunday night watching something on TV. I heard a knock on the door and since my apartment was a very secure building (you have to buzz up to get into the building) I just assumed it was one of my new neighbors I had just met a few days prior. I opened the door only to find a (very drunk) Jim standing in front of me. Before I could really say anything, he pushed his way into my apartment and sat on my couch.

Maybe it’s the fact that I’m super stubborn and tend to think I can take care of myself OR maybe I was just naive (probably that one), but I wasn’t worried. Though I barely knew Jim, he didn’t seem like a bad guy so I just assumed I had a drunky face on my hands. Granted, he was a 6’2″ buff drunky face, but whatever. I went into my studio and asked him why he was here. Here’s the conversation.

Jessie: Hey… so, how’s it going? How did you get into my building?
Jim: How come you never texted me?
Jessie: You didn’t text me either. But seriously, how did you get into my building? How did you know which apartment I was in?
Jim: Oh, I was downstairs, looking up your name on the registry and someone walked in so I just followed.


Jim, patting the seat next to him on my couch: Wanna watch a movie?
Jessie, trying to figure out how to get him outtttt of my apartment: Well, I have a really busy day at work tomorrow, so can we do a rain check? How about later this week?
Jim: I don’t understand why you never texted me. You’re attracted to me, right?
Jessie: Really, Jim. I have a busy week this week. Just text me tomorrow when you wake up and we’ll plan something.
Jim: Are you not attracted to me?

At this point, I was starting to get mad. Should it have been nervous? Probably. But remember the part about me being super stubborn and assuming I can take care of myself? Forgetting that I’m literally half his size. Yep, that’s Jessie for ya.

Jessie: Seriously, you’re drunk. I’m tired. I have shit to do. Call me tomorrow and we’ll figure something out, okay? Really, I need you to leave. I’m so tired.
Jim, getting up from the couch: Fine, fine, fine. Whatever.
… Jim then moves from my couch to my bed which is five feet away (thank you, studio apartment)
Jim, sitting on my bed: Well, why don’t you come over here and I’ll find a way to wake you up.

And this is the point where Jessie goes fucking crazy.

Jessie: GET OUT OF MY APARTMENT RIGHT NOW, YOU ASSHOLE. OUT, NOW. *Other expletives that I don’t remember*
Jim: Fine. Prude.

He got off my bed, tried to give me a hug (seriously, guy??) and walked out of my apartment.

I barely slept that night again, because I was mad. Mad at him for being such a douche bag. Mad at whoever in my building let in crazy drunk face. Mad that I am too nice and let him into my apartment without much fight. Mad that all guys (in my mind at the time) were complete assholes and OMGI’MGOINGTOBESINGLEFOREVER.

Of course, looking back and after telling the story to a few people I realize that I *probably* should’ve been scared in that situation. Luckily he ended up just being a drunk bro who wanted to have a female companion for the night. I understand that the situation could’ve been much worse.

He did text me the next day asking when our rain check date could be. Again … SERIOUSLY? I told him never to contact me again, but after a few more texts from him over the next week, I blocked his phone number. Unfortunately, though Milwaukee is a bigger city, I did still end up seeing him out a few times, but luckily I bruised his ego enough that he never came up to me, just sent me sad eyes across the bar every time I saw him.


And that is my scary online dating story that could’ve been a lot worse! Thank God for that. I still don’t know why I ever continued going on the sites, but hey …

Do you have any online dating or regular dating horror stories? What would you have done in my situation? 


  1. Katie Elizabeth says:

    I feel like you can just tell when a guy is someone to be scared of and when he’s just being a drunk idiot! Thank goodness all ended okay though – now I’m off to read your other story! Thanks for the entertainment 🙂

  2. Megan says:

    Weirdo! Why would he just randomly show up after weeks of not talking?! And then just hang around in your apartment? I would have probably been freaked out if he stayed so good thing he left when you yelled at him!

    • Jessie says:

      Yeah, he was a crazy, crazy guy. I still can’t believe after ALL that, when I would see him out he acted sad that I wouldn’t talk to him. HELLO?!

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