Dating as a Millennial: The Horror

man with flowers, dating as a millennial

*Warning: The following post includes explicit language as well as adult themes of dating as a millennial. Reader discretion is advised.

Dating as a millennial is a mine field, and I’m losing limbs like it’s going out of style. It’s a new era of dating (if you can even call it that) and one more thing Forbes and The New York Times can add to the list of things we suck at.

I know everyone has bad dating stories. You have to kiss a lot of frogs to find your prince blah, blah, blah, but the dating world as it is today is not the one I was told about growing up (we can thank dating apps for that). It used to be that yes, you meet a few ass hats here and there, but in general, most guys were at least decently nice and had a respectable level of emotional intelligence. The chemistry might not have been there, but the basic understanding of dating was. After a lot of over analyzing, I think that is where the root of the problem lies—millennials literally don’t know what dating is let alone how to do it. And if for some reason you do, like me, you’re viewed a super traditional, prude and relationship obsessed, but that’s a post for a different day.

I’ve recently turned my outlook around and have decided to have fun with it—a little comic relief if you will. From funny to offensive, both pathetic and horrifying, here are some of the highlights of my dating life from the past year and a half. It’s not lookin’ good folks.

Having gone out with several guys close to my age mid-twenties and failing horribly, I decided that maybe I just needed to be with someone older. I’ve always been very mature for my age, so yeah that’s it, I need to be with someone older.



Perpetually Single: 35, business owner, home owner, never married, no kids, career focused…you get the picture.

We met at a bar and hit it off enough that I gave him my number at the end of the night. We got drinks several times in the following weeks, and it was going okay. I wasn’t head-over-heels by any means, but was trying to give it chance. Let love grow as they say. It was probably the fourth time we had met up to “grab a drink” and the red flags really started flying. We both come from big families so naturally we started discussing our siblings and I started talking about one of my sisters (who’s 20 years old) and he asked if she had a boyfriend or anything. Knowing my sister really well, I laughed and said, “oh gosh no, I don’t know if she’s ever kissed a boy. She’s really shy, but knows what she’s looking for in a guy”

Him: “OMG, what? She’s never kissed guy? Nothing? OMG, that’s crazy. There’s no way!

Me: *kind of off put “I mean maybe she has, and I don’t know, but I mean, I know my sister and she’s really independent and has never been boy crazy, she’s just waiting for the right guy.”

Him: “Is she autistic or slow or something? That is just not normal, wow!”

Me: “What?! No she is not autistic! She’s a nice girl who is scared of being taken advantage of and waiting for a nice guy.”

In hind sight, I should have gotten up right then and left, but we changed the subject to his family. Honestly I think I was too in shock that he just asked me that to even move.

He has several nieces and nephews and while telling me a story about them he goes, “Yeah my nieces are crazy. They’re such little bitches.”

I must have had a mortified look on my face (OBVIOUSLY) because he started to back track…

Him: “Oh, should I not have said that?”

Me: “Uh yeah, I don’t really like that word especially about a little girl, it really sends the wrong message.”

Him: *very sarcastically and laughing “Oh what should I say then, sassy?”

Me: *crickets, baffled “Uh, um…seriously? What?!”

Him: “Oooooh…are you one of those feminists?”

Me: *smoke coming out of my ears “Yeah, I am and someone with basic human decency! This isn’t going to work out.”

I got up and left. I’m still baffled. This is a 35-year-old Grown. Ass. Man! What?! ….Yikes.

Arrogant Lawyer: 31, tall, dark and handsome, cultured, well-educated, can hold a conversation of substance—also, a fucking douchebag.

I was out with some friends. We had just left a concert and wandered into a bar down the street to get a drink. This guy was really tall so he stuck out from the crowd and for whatever reason, our eyes kept meeting from across the room like we were in a Jane Austin novel or something. He finally approached me and we talked the rest of the night. I gave him my number,and we continued to talk the next couple of weeks, but never met up again. He would call me at midnight or 1 a.m. on the weekends, ask what I was doing and tell me to come over. Annoyed at this point, I finally asked him what his problem was. I had made it clear I wasn’t looking to be a booty call.

Him: “I’m just not looking for anything serious.”

Me: *rolling me eyes, if I hear one more guy say that too me…. “Okay, that’s fine. I’m not either. You realize there is this in-between thing called dating where you can hangout with someone and have fun getting to know them a little. And no, it doesn’t mean you’re in some super serious, committed relationship.”

Him: “Yeah, but girls never want that…blah, blah, blah…just come over, nothing will happen.”

Me: “Yeah, I’m good. Have a good night.”

Flash forward literally six months from when we originally met. He saw I was downtown (thanks Snapchat) and texted me asking to meet him for a drink. Slightly drunk at this point, I said fuck it and met up with him. We got a drink, I gave him a bunch of shit and basically asked him again what his deal was.

Him: “Well a lot of girls I meet just talk to me because I’m an attorney, and they know I have a lot of money and am successful. I had to make sure you weren’t one of those girls.”

Me: “What?! Oookay, well I’m glad you think so highly of yourself, but I’m also well-educated, have a great job and don’t need your money, but great glad I passed your test. I’m good though.”

I left and met back up with my friends. We all laughed about how absurd the whole thing was and what a total prick he was. I thought that would be the end of it, but later on that night, he started messaging me on Snapchat in reply to my story. He messaged me and said I have hairy arms (1st of all good one, what are you 10? 2nd of all I have hair on my arms like any normal fucking person!). I told him to stop messaging me, and he just kept telling me to come over. I responded and said I’m not interested, stop talking to me. Before I had a chance to block him he replied with, “No problem, I’ll just masturbate tonight to the thought of you riding my dick.”

Again, completely baffled still. 31-years-old and what would appear to most people as a fully functioning member of society. More like a waste of space.

Moving right a long…

Bumble Trouble…27, tall, dark and handsome (guess I have a type—who doesn’t have this type though? come on.), very athletic, fire fighter, EMT, lives on his own—socially inept.

All of my friends are in serious relationships, so my dating life has become entertainment for everyone. They convinced me to make a Bumble profile, and I went along with it thinking it’s not like it could get any worse. I actually know people who have met on Bumble and have been together for years. Maybe this is actually how people my age meet now and date.


I could write a whole series solely dedicated to online dating fails, but we’ll just start with this one. For those of you who don’t know, women have to message the guy first on Bumble. This is supposed to help alleviate all the creepy guys messaging you sexual stuff and unsolicited dick pics (again, stories for another post). So I message this guy something very basic, “Hi! How’s your week going?”  Not expecting this answer at all, I opened up Bumble and read:

“Insert my name, I am only looking for someone to have dirty sex with nothing else. If that offends you please let me know.”

LOL, like what?! Even if that’s honestly what you were looking for, that’s what you decide to go with right out the gate?! Bro, at least try and have some game.

I just thought this was funny so I responded and said, “not offended, just not looking to be a booty call. Appreciate your honesty though. Thanks for being so straightforward!”

He responded, and thanked me for also being honest and something else about how he wished he was looking for something more because I seemed really cool.

Yeah, yeah, k whatever….I never responded.

Flash forward three months. I had deactivated my Bumble account at this point, but this dude found me on Instagram somehow and slid right into my DM’s. He said he wanted to go on a date and that his emotionless sexcapades left him feeling lonely, and he didn’t want to be like that anymore.

Yeah, okay, because no guy has ever said that before to get into a girl’s pants.

Trying not to be a total asshole (maybe he really was going through something and is trying to be better) we exchanged messages back and forth. He also added me on Snapchat (quite the social media stalker) and low and behold the dick pics start flowin’ in. Right before I blocked him, he sent me a message quoting Jason Aldean’s song “Big Green Tractor”.

Him: “Hey girl, you wanna take a ride on my big green tractor?

*Sends dick pic

“I can go slow or make it go faster”

Me: *bursts out laughing—crying actual tears.

Is this a joke…this has to be joke…he can’t be serious?

I was going to respond and say something super snide, but I almost started to feel bad. Like oh, hunny…no, no. I think he was like really proud of his dick. I decided to show some mercy to this one and didn’t respond. Somewhere out there is a girl who would love to ride his tractor and who am I to deny her that.

These aren’t even a fraction of the stories I could tell, but I’m already bordering a novel. Essentially dating as a millennial is straight stupid. So long are the days where it was actual relationship drama. It’s just sad now. So here I’ll be with my keyboard and glass of wine channeling my inner Carrie Bradshaw. If I have to go through it, we might as well as get a good laugh out of it.

‘Til next time,

Distressed Millennial Girl

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I give a voice to the women who are concerned about sharing their story publicly. My mission is to give a voice to the women who want to start conversations, but who are concerned with sharing their identity, for one reason or another. My posts don’t reveal personal details that can identify particular people nor do I promote bullying or bashing others. I am designed to give women who can’t share their names an equal voice in the important conversations we are having at She In The CLE. Want me to share your story? Submit a post at

8 CommentsLeave a comment

  • Can this be a series please? I want to take you out for wine so you can share more stories AND set you up with someone better than these terrible creatures. Gosh, it’s hard to pick which one was the worst. But so funny (and disturbing) to read.

  • I met my husband on almost 8 years ago. I met quite a few guys on there, but he was the only man I met on that site that didn’t ask for nude pictures nor did he send any…so, he was the only keeper.

  • How does anybody get married these days? I can’t say my online dating was much better. I do have one great come back to all those pricks, I heard it from Wanda Sykes. “Oh honey, there isn’t enough tequilla in Mexico.” Send that to him just before you block him.

  • I’m DYING reading this…because I lived it too! Online dating is so crazy. I was on Match, Yahoo, and Plenty of Fish back in the day and yeah, the stories are unbelievable. Thankfully dick pics weren’t such a big thing (ha ha ha) back then, but lots of rude, suggestive comments were the norm. I started meeting for the 1st time ONLY over coffee – daylight, no alcohol related impairment of judgement and super fast to escape from. If they refused, they weren’t the guy for me.

    I too hope this is an ongoing series!! Love your writing and your stories. Plus we have to capture all this before you find Mr. Right. 🙂

  • Girl. This is totally relatable.. want to get together and start a bumble/tinder nightmares of Cleveland?? Lmao! But seriously, I have never read something so relatable to my actual dating life.

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