Chronicles of a Serial Dater

If you are also a part of this digital dating age, then you know the woes that come with trying to be wooed. If you’re lucky enough to already be in a stable relationship, or you have made the decision that you are happy and fulfilled in your single life, then let me do you the pleasure of filling you in on what it’s like to try to date in today’s day and age. I’m a 27 year old woman interested in men so the stories and examples below are from men whose ages range from 25 to 34. Get ready for a doozy.

The Hitlist 

Before I dive into some lengthier dating tidbits, here is a running list of the things that men have either said directly to me or in their dating profiles. I promise, none of this has been fabricated or embellished. 

#1: “No woke here, I am an American, I drink beer, liquor, eat steak and listen to country.” Ok… thank you for sharing…

#2: I had been chatting with a guy on Bumble, and after about an hour of going back and forth about narcissists it became apparent that he didn’t really want to get to know me. It seemed like this guy just wanted advice and knowledge on how to deal with narcissists, and I wasn’t feeling the conversation anymore so I stopped responding. It had been less than 24 hours since I last responded and he decided to send this message, 

“did you take off on this? are you a narcissist?! wouldn’t that be cause for some very painful self-reflection.” 

No dude, just because I don’t want to keep giving you free advice and am no longer interested in having a conversation with you, that doesn’t make me a narcissist, #thankyounext.

#3: I had matched with another guy who seemed sweet and put in a little effort (how romantic). After a phone call, a few conversations, and some social media deep-dives it became clear that we were not compatible. I was sensing some controlling behaviors and then found a picture of him holding what looked like some sort of weapon he definitely shouldn’t have had. I unmatched with him and blocked him on everything (may seem harsh, but it is what it is). This man then found me again on social media and messaged me saying,

“Why you had to block me tho?:( act like I was bothering you we can’t at least be friends? Lol like damn”

Thank you, sir, for validating all the reasons why I wanted to end things with this one message. No, we can’t be friends. 

#4: This other guy’s relationship goal was listed as, “I luv me some white girls. Not that I don’t like other women. But I jus respect how white women get after it and go for it when they see something they want.” Seriously? He proceeded to explain on his profile that he’s convinced that “Insecure women don’t like smart confident guys. Listen if you’re a loser, get the fuck outta my way. I’m a winner. I don’t got time to lick and rub on swollen ego’s.” Again, seriously? Has this approach been working for this guy?

But wait, there’s more. The cherry on top –

“There’s a lot of these ‘alpha chick’ independent bossy types on this app. Just as bitter and jaded as ever. If that’s you. Jus know that the same things ya love about me you’ll hate about me”

After seeing these prompt responses I was speechless. I still have no words. Someone, please help. 

#5: The most spontaneous thing bachelor #5 has done was, “asking a GUY out on a date *insert laughing face emoji* (EVEN-THOUGH I’M NOT GAY) *insert eyes emoji* ….. It was more of a Bro-mance type of thing Lol..’ Hey bro, let’s watch sports!’ *insert a bunch of sports emojis*”

So, if I got this right, the most spontaneous thing he’s ever done was hang out with a guy and watch sports? BUT it wasn’t a gay thing…as if that would’ve been bad. Again, I am left speechless. 

#6: I was told to leave a comment if, “you’re actually looking for a nice guy.” Does this man not understand we are only out here looking for the mean ones?

#7: Another man said, “don’t hate me if I’m still in love with my ex.” No, I don’t hate you, but I would suggest some therapy. He also shared that one of his green flags was “big foreheads.” …Nice. 

#8: One guy shared that he’s looking for monogamy because “I’m a loyalist. I do not want other pussy except a lady that I love.” A modern-day Shakespeare. 

#9: This man said we will get along if “you let me bully you.” He gets it, #6, take some notes.  

And finally, 

#10: This guy wants the world to know that he prefers “a cute dork over a hot ig model.” Honestly, I’m not sure if I should feel offended because there’s nothing wrong with being a hot Instagram model, or because he doesn’t think I could be one. 

Now for some unbelievable encounters that I hope no one can relate to.

The French One

I matched with this guy and after a few conversations, he seemed nice, thoughtful, intuitive, and emotionally intelligent. He shared that he had just moved from France and was still getting used to everything in the States. We decided to meet for dinner at one of my favorite vegan restaurants in the area. 

Other than the typical nerves you get before meeting someone new, I typically don’t get too nervous or anxious for first dates anymore (thank you therapy). However, the entire time I was getting ready for this date, including the drive over and waiting at the restaurant for him, my anxiety was through the roof. At first, I blamed this on the nerves of thinking there could be a language barrier, or that I could make some sort of faux pas without knowing, and first date jitters. Unfortunately, my anxiety only continued to increase throughout the date, and for good reasons. 

I usually take the first date to feel things out, see if there’s a connection, and determine if we get along and have common interests. I understand other people may have different expectations or goals for first dates, but this guy began quizzing me on what I was looking for in a partner. He pulled out his phone and opened his notes app to begin writing down all my “requirements.” I laughed because I thought he was joking, but he most definitely was not. I tried letting him know that made me a little uncomfortable and that I don’t have a long list of “things” I look for, but he kept pushing for me to think of personality/character traits to write down. When he finally put his phone away he told me he wanted to apply for the position of my boyfriend. I laughed because I was uncomfortable and explained to him that I just wanted to see how tonight went and if we got along. 

We started talking about dreams and their meanings, and then he told me he was a man straight from my nightmares. I laughed and said, “you mean straight from my dreams?” He said no, straight from my nightmares. I paused and told him that he may not understand what that means. He began to inform me that he knew exactly what nightmares are and that he was from them. I laughed nervously. 

He then said, “are you scared of me now?” On the inside I became terrified, but there was no way I was going to tell him that. I told him, “no, why would I be scared.” He laughed and told me that I had no idea who he was or what he could do. When I didn’t say anything, he just continued to laugh. I was ready to leave.  

Then he came over and sat next to me in the booth. I was now trapped between a restaurant window and this man who was apparently straight from my nightmares.

He tried telling me all the reasons why we should be together and tried forcing me to tell him when we could see each other again. I tried being vague but then realized he was not going to let up until I gave him a time and place. After that, he tried asking me to go for a walk with him (no way in hell that was happening). I told him I had to leave because of waking up early for work the next day. When we finally got to our cars, I noticed that when he had pulled out of his spot, instead of going in the correct direction, he had pulled out and gone against traffic so that he could be behind me when I pulled out of my parking spot. There was no way I was letting this guy follow me out. When I did back out of my parking spot, I pulled out facing him, going in the correct direction of traffic. Thankfully this forced him to turn around and I followed him out. After that we parted ways, I blocked him on everything, and thankfully I have never seen him again. 

This Only Happens in the Movies

I’ll make this a long story short. After I had come home from yet another terrible date, I got into my comfy pajamas, made myself a strong margarita, and sat down on the couch with some Cheeze-Its and M&M’s (great combination if you’ve never tried it) and began scrolling through Bumble.

That’s when I saw him.

The crazy part is, if my acquaintance had never shown me a photo of her husband or told me about a trip they were planning, I would have never known that I had stumbled upon another woman’s husband. But, unfortunately, I had Bumbled upon his profile. 

I then reached out to a mutual friend who knows me and this other woman to ask for advice. Do I just screen-record the profile and send it to her? Do I ignore it? Could it be some other person using her husband’s photos to catfish? Should I say something to this woman? What if they are in an open relationship, should I ask her? What do you do in this situation?

As of right now, I have the receipts on this guy, and it has been confirmed that he is the husband of my acquaintance. Not sure how else to proceed in a situation like this. Again, someone, please help.

Holding Out Hope

Contrary to what it may seem, not all my experiences on these dating apps have been bad. I have met some fun, interesting, and respectful guys but for whatever reasons it never turned into anything serious.

Everyone from my manager to my therapist tells me that it only takes one and he’s out there…I’m a hopeless romantic so I’m still holding on to this notion, patiently waiting for all the stars to align. 

But while I wait, I just have a few questions for you. First, where do the good guys hang out? Second, let’s share in the agony of modern-day dating. I’d love to know what some of your date fails have been or what gives you the ick!? We don’t have to go through this alone!

“Alexa, play Blank Space by Taylor Swift”

Florida born and raised. Jordy began her professional career as an officer in the Coast Guard but has recently transitioned into the civilian world. When she is not obsessing over her fur babies, you can find her at the beach reading or staying up late to embroider while watching the latest true crime docuseries.


  1. I gave up. Not very romantic, but I discovered the guys I did meet had stratospherically high opinions of themselves but seemed completely unaware of this. I kept asking for reasonably fit, and often got dumpy heavy drinkers. Did they think they were so charming I wouldn’t notice? I think the alcohol they kept encouraging me to drink fitted them with permanent rose-colored contact lenses – at least toward themselves. Like I said, after 5 different tries on 4 different apps, over several years, I have come to enjoy my freedom. I wish you all the luck I didn’t have…

    1. Jordy Macbeth

      I haven’t given up just yet, but the single life is looking better and better each day! In addition to the men I have found having inflated egos, they lack basic emotional intelligence and it’s such a turn-off.

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