• Chiara

7 Hilarious but Super Crappy guys I dated in my 20's (and a couple in my 40's- so far)

The last post was a bit heavy, which is ok sometimes because life is sometimes heavy. Let’s lighten things up here and have a laugh at my expense: I’m going to talk about dating. Dating in your 40’s feels a lot like…

Or like



My dating experience this time around has admittedly been quite limited. It’s been just over a year since my husband and I separated, and I had to spend some time sorting my head and my heart out before I even thought of it. And perhaps when I went on my first date it was too soon (earlier this year), and then there was covid, and now things seem to be getting back to normal a bit so maybe, just maybe I’ll have some entertaining stories to regale you with again in the future.


I thought that dating in my late 20’s sucked. I had come through an 8-year relationship and it seemed like most of my friends were in serious relationships, so I didn’t have many people who could fully empathize with my experiences. And you might think that people don’t forget what it’s like to be single and hating having to go on awkward first dates and make small talk, but they do forget. It’s a lot like having a baby… you very quickly forget what it’s like to have to attend to a needy human that demands things from you, that wakes you up at ungodly hours because they need to be comforted, and you feel like you need to constantly make sure they know they are loved and cared for.


Waaaaait a minute. Are we talking about infants or most of my dating experiences? The similarities are unsettling.



When I dated in my late 20’s I was naive, and thought I was ready to take on the world. Well, the world of dating and single men, anyhow. I decided I was in it for the free meals and some funny stories, because I was hurting too much to ever allow myself to fall in love again, and I would never, GOD FORBID - NEVER put myself in a situation where I was vulnerable enough to be hurt that badly again. I did end up with some hilarious dating stories, most of which I wrote down, but of course I can’t find that file anywhere. But to summarize some of what happened (completely from memory), here is a condensed list of some of these dating experiences:

  • The guy who showed up on our first date in very short cutoff jean shorts and a tank top with Mickey Mouse’s front on the front and Mickey Mouse’s back on the back. This guy ended up on a few tv shows, including Oprah - with his wife (yeah, the dirtbag had a wife) because of how awful he was to her. Maybe I should call Oprah and be like “hey- do you want another side of the story?"

  • I spent a few days talking to a guy online and we decided to talk on the phone before we met. Within seconds of us saying “hello”, he said “you sound like you’re fat”. What in the holy moses of peaches? Who sounds fat? And what kind of a jackwagon says that?

  • The guy I dated who made amazing Valentine’s Day plans for us, which included a restaurant reserved just for us, a dessert especially chosen for me that could only be made by a place in California, and a walk by the river which ended by me being serenaded by him. And then he called me, 5 minutes before he was supposed to pick me up and said “So, my ex girlfriend is in town. So I should hang out with her tonight. Oh, and to be clear, she’s staying at my place”. And naive me says “But you only have one bedroom”, and he says “yeaaaahhhhh”.

  • The guy I dated for a month and asked me to go shopping with him. No big deal, right? Well he said he wanted to go into a jewelry store, so in we went. He told me to sit down. Sit down I did. He said “take a look at these rings, pick whichever one you want, there will be no expense spared for you”. I ran out of that place so fast I think I burned a hole in the tile.

  • The time I was set up on a date with a guy who spent the first hour getting absolutely smashed, and then the second hour telling me how stupid I was, how stupid my parents were, and how he felt sorry for anyone who had to spend time with us. Ok, I might be off with my timeline- I think I only let him talk this way for 10 minutes, max, and only that long because I was in such utter shock that I don’t think I could move. The rest of the actual hour(s) spent in the pub I was hiding in the bathroom, hoping he would leave. He didn’t. A waitress eventually took pity on me and offered to usher me out the door. I don’t think he was sober enough to notice.

  • The super sketch bar I was at (ok, I was a regular at, I do love me a sketchy bar), had a super sketch old dude wearing a leather hat and fanny pack, who was eyeing me up all night. He eventually mustered the courage to come and chat with me, and his pick up line was “You sure are purdy. You got real wide shoulders.” (Yes, I did talk to him for a little bit because I acknowledge that approaching someone of the opposite sex takes a lot of boldness.)

  • Lastly, and the piece de resistance, when I got home from a work trip and was really hungry, so I got online and decided to see who wanted to go for dinner with me. A guy from out of town was online and wanted to grab a bite to eat, so we had a nice dinner together and I figured that it was a given that the dinner was only that, dinner, and we’d part ways, having shared a nice meal together. He asked me for a ride back to his hotel, so I obliged. As I went to drop him off, he says “Oh! I have a present in my room for anyone who agreed to have dinner with me tonight. Me, naive, silly, inexperienced me, believed him. So into his room I went, and he went into the bathroom, so I stood there, awkwardly, surveying my surroundings. Cheap suit. Messy room. Gross old food in various containers strewn throughout the room. Mr “Present” opened the bathroom door and walked out - naked. I laughed and told him it wasn’t going to happen, and started walking down the hallway to his hotel room door. Something hit me in the back. I turned… to see a naked man throwing old, dried up potato skins at me. (I realized afterward this was not a smart move on my part, but put this aside, judgypants, and see it as funny because it is!)

Yes, if we don’t find humor in these events, we’ll just be stuck on the floor after drinking too much wine, sob singing to Ray Lamontagne (Speaking for a friend, because I’d never ever do this).


Let’s bring things back to the highly encouraging and promising landscape of my dating life- here I am in my 40’s, trying to navigate this scenery again. Well, maybe that’s an overly optimistic vantage point of dating right now- because it actually looks more like the Sahara or the Rocky Mountains. The weather is turbulent at best. It all looks the same, every dude has a picture of himself shirtless or holding a fish, and everyone LOVES camping. Ok people, do you actually all love camping this much? I don't. So - I'm doomed. If you live in Calgary, like I do, dating seems to be a bit like the weather here… it will change within an hour from sunny and warm to beating you and everything you love with toonie-sized hail, making you wonder why you even bother to live anywhere but a cement bunker where nothing can get damaged. But of course, you come out again because you really really believe that the sun will shine again. But then you get a sunburn.


I decided to do some research into single people, in general at first, and then I dove a bit deeper. In New York City, there are over 200,000 more single women than men. What the heck? That's the population of Saskatoon! Can you imagine only one man living in the entire city of Saskatoon? No wonder those wonderful ladies from Sex and the City (one of my favorite shows) struggled to find a quality man! And get this, according to the National Post, there is apparently “new research that reveals the acceptable ages for people you can date”, and there’s an actual formula - who knew? Here’s the formula: “half your age plus seven years” for dating someone younger than yourself, and when determining if someone is too old for you, you “subtract seven years and double that number.” I don’t know what I’m subtracting seven years from or what number I’m doubling, though, so that part has me completely lost.


According to statistics Canada (who shortened their name to “Stats Can”, like that makes them sound more hip, or something? Wait, is “hip” even a cool thing to say? Maybe I’m the uncool one), the number of available men and women seems to be quite similar for those of us aged 35-50 (women slightly edging out men), so this should be good news for me, right? And to add to my odds… this Covid business likely didn’t do a lot of favors for marriages, right? I mean- being stuck in your house with anyone as much as we have been the last few months; this is a serious test of how much you like a person. So I figure there are going to be either babies or divorces coming out of this forced time together. Imma just gonna sit right here and see how this pans out, mmkay?


Also according to the super hip Stats Can, the verdict around the location of the best ratio for me would be Petawawa (yes, I did have to look up where it is. In case you don’t know, it’s a town in Ontario) where there are 2 single men for every woman, most of this being attributed to the presence of military men. Campbellton QC is where the single men looking for a woman want to go, where the ratio is 12.1 women for every 10 men (yeah, that’s the best I could do in my search for info, sorry my dudes).


Unfortunately, I don’t think I’ll be moving any time soon. If you live in either of these places, let me know! I want to hear about your take on these stats...


As I said, my dating experience has been very limited, but let me share one particular gem with you, because it would be absolutely unbelievable if it didn’t actually happen to me:


It’s covid times, so we have a video chat call instead of a first date in person. He answers the phone in a bathrobe over a golf shirt.


He dominates almost the entire conversation. According to him, he’s smart, educated, irresistible (I clearly remember him using this word to describe himself), very well-off, turns women down constantly, and super fit (and as far as I end up concerned, nobody could ever love him as much as he does).


He starts talking about kids, and the fact that he doesn’t have any kids. He says “So tell me- do you think that I don’t have any children because I’ve never played in the rain or because I always wear a raincoat?”


He drags the conversation on and on, talking about himself, with short and interspersed very pointed comments to me like “tell me how many people you’ve dated”. When the conversation (finally) ends, he demands that I send him a text telling him what I thought about him and to itemize the different things I liked about him. He told me that if I played my cards right, I just might be "the one". It made me reminisce about the notes we used to pass in grade 6 where we asked other kids to rate us 1-10 on our looks, personality, clothes, etc.


So… I relented and sent the stupid text. I was perhaps kinder than I should have been, but I didn’t want to make a knee-jerk decision and wanted to sleep on the conversation before making any concrete decisions.


Morning arrived, and I woke even more bemused, and even annoyed at the conversation. So I sent what I thought was a pretty kind text, saying that some of what he said made me uncomfortable and I didn’t think we were a good fit, and I wished him all the best.


I am going to directly quote from his text reply to me, because I just can’t make this stuff up:


“Enduring lasting peace and security don’t require perpetual war… I’d rather strive to not force as much turnovers as touch-down. Our decision determines our destiny.”



And that is, my friends, who is left out there for me, in this Sahara Rocky Mountain landscape of dating in your 40’s.


I do have hope though, that one day a man will see me and just feel drawn to me, or vice versa, and things just click and it feels right and good and not complicated. I don’t expect it to be easy all the time, but it can’t be hard all the time.


I have learned through some reading, some conversation, and some experience, the following- and I want to share it with my dear, single friends:

  1. Just because these “good and uncomplicated” people exist, doesn’t mean they’re interested in us,

  2. Likewise, we might not be interested in them (boo-ya!).

  3. Make a list of at least 10 things that are “must haves” in a partner. You get a minimum of 10 - let’s not go all crazy and put things in there like “must bring me Reese’s peanut butter cup blizzard at least once a month” in there. (Ok wait. I might put that in my list. That would be so awesome. Take note, future whomever.)

  4. There are, unfortunately, lifeguards in the dating pool. Be the one who lets the duds find their way to the bottom of the pool. Don’t keep trying to salvage a relationship that isn’t worth your time or that drains you. You’re worth it.

  5. Trust your gut and go with your heart. If something isn’t sitting right, don’t try to make excuses for it. Those things that irk you a little now won’t go away, and they could potentially be red flags.

  6. You are enough, just as you are. You don’t need someone to complete you. Your relationship with yourself and how much you love yourself is more important than what someone else can bring to your life. Just try to find someone who makes the world a better place to wake up in.

I know that online dating is a horrible, vapid place of rejection and disappointment. People who don’t even know you who have (or more likely haven’t) read a few lines about what you think is the best way to present yourself decide in that moment whether to potentially get to know you better or throw you in the online trash bin. It’s highly demoralizing, if you allow it to be.


For example, I'm checking my email tonight, and Bumble be like:




So I'm all like "Sweet! Yes! I'm buzzworthy!" and I head over to my Bumble app. But my Bumble app be like "Dang girl, you aint got no matches. You need to 'expand your filters' to include men you'd never consider dating"...





I have a tough time stepping away from dating sites. What it does for/to me is similar to Facebook; the external recognition, acknowledgement and affirmation is hard to turn away from. Why do we seek and feel like we need this type of reassurance from people that don’t know us? Or even from those that do, in an online manner? Anyone worth having in your life will acknowledge your inherent worth, in person, just as you are. You know what, I’m going to take these words seriously and cultivate a relationship with myself, to learn my inherent worth and to know who I am, and therefore what I have to offer. I'm going to take a break from online dating (yeah I know this means less funny stories in the immediate future). Because relationships that succeed need to be more selfless than selfish, more about “what can I offer you?” than always expecting the other to meet your needs. Two people who know what they have to offer and whose goal in the relationship is ensuring the other person feels loved simply cannot fail.


Anyone who knows me well knows that I don't like chick flicks. The fact that it's just SO out of touch with reality irks me; nobody falls in love like that. But- Bridget Jones's Diary has a special place in my heart, and when Mark Darcy tells Bridget that he likes her just as she is, it makes my love-grinch heart grow 10 sizes. We deserve to be loved well, to be seen, to be heard, and to be cherished, just as we are. Not the fitter, richer, more put together, less enigmatic, more successful version that you think you need to be. Just as you are, right now, in the skin you're in, in the place you're at. I've decided I won't settle for less than a David and Patrick love (please don't ruin it for me if they break up, I am late to watching Shitt's Creek and it might break my heart!). I was telling my friend that I admire David and Patrick's relationship, and she asked why. I paused for a moment not really knowing exactly why it touched me and made me teary on a regular basis, and then it struck me: Patrick sees David, truly sees him as flawed and faulty and a bit neurotic, but believes in his inherent worthiness to be loved. Patrick doesn't love David in spite of these things, he embraces them as part of who David is and loves all of it. And it is such an amazing example of someone not even understanding why someone loves them so much, but then allowing themselves to be vulnerable and allowing themselves to be loved by someone who sees them for everything they are.


David (and Sinnead O'Connor) say it best, and this is what I know to be true of you:




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Hi! I bet you missed me. Or maybe not, but here I am again, with some of my words and musings and hopefully something that will make you smile a bit too. Because nobody thinks I'm as funny as I do. I'