Misadventures in Dating


Dating after having kids or being married is not for the faint of heart. In fact, it’s a roller coaster — the kind that makes you throw your hands in the air and wave frantically at the attendant, hoping he sees it and stops the ride before you lose your lunch. There have been some great dates with some great guys, but there have also been a handful of dates with guys that left me shaking my head and texting my friends as soon as I could!

So, let’s talk dating. Dating after kids is tough enough without having to come face to face with some of the crazy characters that show up on your doorstep! 

Dating Misadventures

The guy with mommy issues

He’s 27, really handsome, has a successful career and a great big family that he’s really close to. So close in fact that every time we went out he was looking over his shoulder constantly. After asking him a few times what the deal was (“Are you embarrassed to be seen with me or something?”), he finally admitted that he was terrified that his mom would find out he was dating an older woman. He wasn’t actually afraid that his mom would walk in, but that someone she knew would, and that they’d automatically know that I was 10 years older than him. This paranoia got to the point that we didn’t go out, but stayed in instead. At that point we decided this wasn’t going to work since we weren’t gonna just hang out in my living room forever. 

The guy who thought he was Christian Grey

Let’s just assume that you know who Christian Grey is. And if you don’t, Google it. Again, late 20’s (28 to be exact), great career, beautiful condo on the river downtown, gorgeous, fun guy. Drinks went well enough that we decided to hang out longer and watch a movie at his place. I was blown away by the gorgeous views of downtown & the river from every room in his condo, but nothing could prepare me for when he lifted his mattress (while showing me the view from his bedroom) to show me the “equipment” he likes to use. Yes, that kind of equipment, complete with cuffs for both wrists & ankles. And I won’t even get into the other things he mentioned. He said that his friends call him “Christian.” (Insert HUGE eye roll.) As if all of that wasn’t enough, the second time I went to his place, (Yes, I went back. Like I said, dating is hard.) he had a fitted sheet on the couch and told me to just “take your pants off and get comfy.” No thanks, dude. I’ll keep my pants on. I decided that was about enough of his kinky crap and I high-tailed it out of there. 


The guy who had lots of money, but not really

This whole online dating thing is strange to me — the apps, the swiping right, etc. So, I usually at least check someone out on Facebook before we go out. This guy looked pretty normal and cute in his baseball cap, so we go out. Turns out he’s not nearly as cute in person because he is suuuuuper boring. When he asks me out again, on a day when my kids are with their dad and I have nothing to do, I oblige. Might as well right? Maybe I was in a bad mood the first time or I was letting hunger cloud my judgment. This is when things got a little weird. He spent somewhere around a grand, yes one thousand dollars, on me at Nordstrom. Long story short, it turned out he basically just wanted a companion to spend money on, etc. After weeks of not going out with him again (because frankly, I was weirded out), I finally Googled him and discovered he’s got a shady past that includes things like embezzlement, stealing thousands from an ex-fiance and being disbarred. Ladies, I can’t make this stuff up. Phone number, officially blocked.

The Worst of the Worst

Tall, dark and handsome. Check. Drinks at a fun place. Check. Great conversation. Check. An invite to hang out and watch a movie, double-check. After all, everything was going well! Until he opened the door of his place. I kid you not, there was trash stacked about 4 feet high in his kitchen. No exaggerating, it was bad. The living room? Trash, and papers everywhere. Oh, and broken glass. Yes, broken glass on the floor. Nowhere to sit on the couch or the chair, because papers and clothes and crap everywhere. “It’s a mess, I know. Sorry.” (A mess? More like, you’re a freaking hoarder, dude!) I’m already questioning what the heck I’m doing there when he says “we can just sit on my bed and watch a movie.” You’d think I would have known better by now, but I gave it a shot. So, I sit and within .5 seconds he grabs my hand, moves it to his lap and tells me to call him “daddy.” I immediately jumped up and declared I’m leaving. After all, we’d had the whole “no hooking up on the first date” talk before going out. He arranged an Uber and I ran out the door and downstairs, not even saying goodbye. Luckily the Uber drive is there already and I hop in. Phew! Glad that one is over, right? Nope! Halfway from the east side to Tosa, he cancels the Uber! So my driver won’t get paid. SO gross. I text him with some not so kind words and block his number. 

And if this weren’t enough, we asked for more crazy dating stories from our team and BOY, did they deliver! 

The guy with the crazy wife

The one time I met a guy for frozen yogurt and he casually mentioned “his wife.” I stopped him right there —”your WIFE?” His response? “Well she’s crazy, in and out of psych wards, so it doesn’t really count.” Um, yes…..that counts, dude. Bye. 

The guy with the tie-dye

After being married for nearly 20 years, I didn’t know how to date. I didn’t even know how to FIND a man, let alone how to DATE one, so I did online dating. One guy definitely stands out. Heck, he would stand out in any crowd! It was the dude with a tie-dye collection. Yes, he had tie-dye shirts for every occasion. Who knew there were “formal” tie-dye shirts? I rewrote my profile after he contacted me because I couldn’t figure out what in my profile would have made him think I’d be interested in TIE-DYE?! 

The Exorcist Guy

This one is almost too crazy to believe, but it’s totally true. A guy I was seeing once tried to exorcise the devil out of me. Apparently, he felt lust when we were together, talked to his Pastor’s wife about it and she said I must be possessed by the devil. He held me down on the floor of his apartment and yelled “Fight back! I know you are in there!” The only thing I could reach was the stalk of a large corn plant. I grabbed it, thinking the pot might knock him out, but the plant came out and I ended up slugging him with the root ball. Some dirt got in his eyes and I was able to get loose and run. Needless to say, I broke up with him.

Glad to know I’m not the only one who has experienced some crazy dates! 



  1. My daughters, both in their mid-20s, have told me about the Angel Shot because I worry about meeting someone unsafe online. If you are ever at a bar and a date goes sideways, order the Angel Shot. Here’s how it works: Order an angel shot neat and a bartender will escort you to your car. Ask for it with ice and the bartender will call a taxi or Uber for you. Order it with lime and the restaurant staff will call the police. Maybe something for all ages, lol.


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