Dating,  Live

My Top Five Dating Disasters

The wild ride of dating apps and all the entertaining but terribly wrong dates I have been on.

My dating journey has been interesting, to say the least. I do have a lot of guilt, somehow when you are in your twenties your friends and family could care less about who you are dating, but once you hit thirty the pressure is on, to put yourself out there and actually make an effort. And when I say effort, I mean effort. Swiping, texting for months, scheduling dates, rescheduling dates, fitting them into your schedule and then doing the whole process all over again. Dating is a full-time job and some men have no idea how to date. You have to be a detective and make sure the guys are fully single, not psychos and its an added bonus if they are gainfully employed.

One of my Hinge matches, who I have yet to meet, I’m hoping this is because it is Corona season, suggested I post about my dating experiences; so I rounded up my most entertaining dating stories to help you ride out quarantine season.

The Actor

The actor was the closest I have gotten to being catfished. He proceeded to tell me that I look better than my photos and that he was pleasantly surprised. He tried to compliment me by telling me that most people’s photos are at least ten years old or they are fatties that take close up selfies (his words not mine). I didn’t have the heart to tell him, that he was part of the earlier category, given that his hair was quite a bit longer than his photos and he was now rocking Captain Morgan’s facial hair.

He is not only an actor but an all-around artist, he is writing a screenplay, writing music, creating art and location scouting by day. He was very proud of his work and offered to show me a naked portrait of his ex-girlfriend that he had painted, I declined.

Like the gentleman that he is, he picked up the tab and as the waitress left he says to me “Your place or mine?”. Um….yeah sorry, this was not where this was going at all.

Ear Plugs

This was a total error on my part, sometimes I get super busy and I think I can just do it all and in this case, I thought I could squish in the first meeting with a friend’s birthday. It was a mixed group of us (guys and girls) hanging out at a bar, so I thought why not, the more the merrier. The guy arrived with his brother. They both seemed pretty intense. They spent the majority of the night talking about their father. He lived right next door to his dad. He went on to tell me how they go there in the morning for breakfast, then go to the gym together, then work together, and then cook dinner together. I kind of poked fun at him for it, but he wasn’t picking up on my sarcasm. I love my family too, but this seemed like a lot. I tried to diversify the conversation, but somehow it always reverted back to a father-son story.

My attention span was dwindling, so I said that my friend and I were going to get up and play some games, with the hopes that he too would take it upon himself to entertain himself. He instead, sent me text updates of where he was, from going to the bathroom to grabbing a drink to returning to our table. He then came to check on me since I hadn’t returned the multiple texts, so he thought maybe I couldn’t find him. Ok…this is a little bit rude on my part…but I just wanted to have fun. He tapped me on the back and when I turned around to speak to him, he said that he couldn’t hear what I was saying because he had to put his earplugs in because it is “way too loud here”. We were at a speakeasy bar! I politely told him that I would love if he and his brother decided to take off because I think this was more of a friends hang out and I don’t think I can continue to entertain them. Needless to say, I learned my lesson and this was definitely not my soul mate.

The InstaFamous Dog

I went on a date with a fairly normal guy. The only goal I had for the summer was to date a guy with a dog, so I was so happy to meet a man with a pup. He text me updates of the dog, obviously, because I am a crazy dog person. Send me a shirtless selfie, I could care less, but a cute dog video, I am there.

I was showing my friend my new love, the dog obviously, and she responded saying that she knows this dog…she pulled up the Instagram account which is curated by Mom and Dad. Yes, mom and dad are still together and in a long term relationship. Why are men the worst? Be smarter, don’t use your instafamous dog as bait!

The Drunk

My humor is a little bit playful and I like to poke fun at people, arriving smashed to a date, is basically asking for me to play with you a little bit. It was another case of super outdated photos, but I appreciate a winning personality, so I am going to give this guy a fair shot. He mentioned that he had been drinking by himself all day. Alright, we are off to a good start. He is currently crashing with his friend, who is a girl, and may or may not want more…not sure about that situation.

We sit down and he proceeds to tell me how he wants a housewife that he can take care of and lucky me I can be that housewife. Not a goal of mine, but I appreciate his optimism. He also suggests I put more photos of my face on my profile in order to be more successful at app dating, apparently, I am selling myself short. Not a compliment just some constructive criticism.

He proceeds to tell me that he hasn’t worked in ten years and lives off a recycling program…in my head, I am seriously hoping he is not talking about returning his empties to the bottle depot…cause that will not support the housewife lifestyle that he has been pitching me all night.

I try to have a fairly regular conversation, but all my questions put his back up, finally, he turns to me and says, “lets fast forward and have the conversations that people have on their sixth date, not their first date.”

I responded honestly and said, “It has been a long time since I have gone on a sixth date.” in my head thinking this is why!

The Blocker

It takes me a while to develop feelings. I tend to be pretty aloof and then a switch goes off in my head and I start to get invested. I actually don’t even save numbers in my phone because then I would have five Aarons, ten Bryans and three Michaels. Dating these days is fleeting, so if you are in my contact list, I have decided you are officially part of my life.

I went on a few dates with this guy, he was quite sweet but I just felt like we were on different pages. One of my biggest fears, when it comes to relationships now, is ending up with someone who doesn’t know who they are. The vibe that I was getting from this guy was that he was quite lost, so I gently told him that I wanted different things and that perhaps we are not that compatible.

Well maybe we were on the same page..but moving in opposite directions. He sent me a few shirtless Snapchats, silly me, its 2020, I just assumed he must spam his contact list to drum up some business…I was wrong. By the third shirtless photo, he messaged me asking if I don’t like what I see. I didn’t know how to respond, so I said oh sorry, I didn’t realize these were specifically directed to me.

A week later, I get a request for a new Snapchat friend. I guess he didn’t like my previous response and had deleted me in anger. Again, he sends me a shirtless photo and asks me if I want to hook up. I now have to be blunt, so I say thank you but it is just not what I am looking for right now. He then responds saying, I know it is not what you are looking for, but why don’t we have some fun in the meantime…

What’s that quote from Wayne Gretzy…

“You miss 100% of the shots you never take”

-Wayne Gretzky

They Aren’t All Bad

There are multiple times when my girlfriends and I are chatting and we are dying laughing about our dating stories. We have toyed with the idea of throwing together a podcast, but I think after a while it would get a little bit boring. Just a series about ghosting, guys that live with their parents and weird fetish stories.

To be honest, they are not all bad. Some people are lovely but there is just no connection, or there is a connection but you want different things. I do enjoy making new friends when possible and collecting these horror stories to share as cautionary tales on my future dates.

Do you have some stories of your own? Let me know in the comments below.

Vancouver based lifestyle blogger. Visit my blog and discover travel guides, fashion tips and recipes.


  • Katrina

    About a year ago I met up with a guy at a brewery and we had a great time. He was friendly, smart, easy to talk to, attentive, nice looking, and got the tab. All candidates for a real date, so I accepted when he called a few days later. He suggested we meet downtown and walk around to find a place to eat. Sounded good to me! It’s summertime and Florida, so I show up in a sundress and comfy sandals. He shows up in full jeans and a JACKET! Okay….(I had no idea what he was thinking wearing that in Florida but whatevs!) So we start walking around and I immediately notice he’s limping (and sweating!). I asked if he’s okay, if we should walk slower, and if his leg is okay and he completely dismissed it and changed the subject. Okay… so I just do my thing and he’s panting, sweating, and limping behind me as we “walk” around and find a place to eat. At dinner, he says he’s not hungry. Okay… So I order a meal and he watches me eat and only orders drinks for himself. At this point I realize we aren’t going to see each other again after tonight. I eat kinda quickly, and we start to walk/limp around town again but I walk in the direction of our cars. We were 10 mins away and he all of a sudden says “oh no! I’m so sorry! I can’t hold it!!!” then whips out his dick and pees on the sidewalk. There were people around us! It was dark and night time but we were in public!!! I kept on walking and he limped behind me and that’s the last time I saw him. Now top that one, Jaemie! 🤣

Leave a Reply

Your email address will not be published. Required fields are marked *