Real Women Share Dating Horror Stories:What Was I Thinking?

A look back at the mistakes we have made
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happy couple

My friend Alex is a professional chef, and just got married two months ago. She opens the conversation when she tells us, “If you’re dating someone who lives at the Salvation Army, run.” At first, we think she’s kidding, but she’s not.

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A few years back, Alex started dating the hottest, sweetest man she thought she had ever met, until after a few dates into it, she began to wonder why they always went back to her place. Alex explains, “He was really kind and nice, and head over heels in love with me, but he lived at the Salvation Army, and then of course, I let him move in with me because well, he needed a place to live. After a few months, I woke up to what I was doing and broke up with him. We really weren’t on the same path. A week later, he hooked up with one of my friends, and ended up marrying her. Bullet dodged.”

Mimi, on the other hand, found herself with Mr. Homeless’s opposite: “I was in high school, and Jason looked just like Leonardo DiCaprio, from Basketball Diaries, not Titanic. He was loaded, had a hot car – the perfect prom date. I dated him for nine months, and he cheated on me with my best friend since I was five years old, then with his ex-girlfriend, and then another girl who he swore was just a “friend,” and I still went out with him. What can I say? I wanted that prom date, and in the pictures, it still looks like I went with Leonardo. Sadly, that was just the beginning of a long line of mistakes.”

Janelle has her own horror story – straight from the Internet. She explains how when she first started Internet dating, she met this really nice guy. She continues, “I didn’t tell him where I lived because I was actually pretty wary about that. The next day, he called me and asked if I wanted to go out again. I liked him, and I was like, ‘Sure. Where do you want to go?’ and then he tells me, ‘Well, I’m standing outside your building right now so wherever you want to go is fine.’ I realized that my first Internet date was a stalker. In a way, I guess that was a mistake I didn’t make because we never had that second date.”

The conversation turns to me, what was my worst, “What was I thinking?” moment. Was it the porn addict? Was it blowing it with the prince? Or was it the many times I rejected the nice guy for the creep? I am getting measured in my underwear by Mimi, when I realize, my biggest mistake would be giving up on the relationship I am in now. I recently read Women, Food and God: An Unexpected Path to Almost Everything by Geneen Roth. In it, Geneen writes about wishing her husband would die. She fantasizes about this for two reasons: one, she would be free of him, and two, she could get the pain of his leaving over with.

She is not alone. I often imagine looking at my sweet, wonderful boyfriend over a dinner of Trader Joe’s chicken lasagna, inhaling painfully, and saying, “I don’t want to do this anymore, and I want you to leave.” Sometimes I hear the words so loud in my head, I almost say them. The funny part is that I, much like Geneen, am madly in love with the person I am with, but then he refuses to turn off the Clippers game (the Clippers?!), or he won’t stop talking about politics, or he’ll forget to put the milk away, all I want to do is run. It appears that after years spent making mistakes, I am scared to really sit in a relationship and learn from them.

For every homeless dude and Leonardo DiCaprio look alike, the biggest mistakes weren’t the bad guys we dated, but the good guys we rejected for them. I know if I shocked my boyfriend with a mid-dinner breakup, saying things I didn’t mean, and breaking both our hearts for speaking them, it wouldn’t take me long to say, “What was I thinking?”

After the fitting, the four of us head to lunch, and on the way, we find ourselves standing at a stoplight with a homeless man. Welcome to downtown Los Angeles. He starts telling us how pretty we are, and asks if we’re married. Alex says she is, Janelle says she’s engaged, and even though Mimi and I break into an impromptu rendition of “Single Ladies,” Janelle tells the homeless man that we both have boyfriends — boyfriends who don’t cheat on us, or stalk us, or live at the Salvation Army, as our homeless suitor most likely does. He laughs, “I figured you ladies were all taken.”

And after decades of dating mistakes, we finally are. As I look around at my friends, I realize we’re all also taken by really good, honest, and loyal guys. But that doesn’t mean there won’t be days where they do something really annoying, and we go, “What am I thinking?” The real challenge is realizing that we’ve stopped making those old mistakes, and it’s up to us not to start again.

Kristen McGuiness is author of 51/50: The Magical Adventure of a Single Life. She lives in Los Angeles.


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0 thoughts on “Real Women Share Dating Horror Stories:What Was I Thinking?

  1. danyelz24 says:

    LOL Try being in your mid 40′s and having to get back into the dating scene!

  2. need2no says:

    There now..back into the dating world and it sucks….not too sure about current boyfriend, seems a bit shady!

  3. NYSurferChick says:

    They’re ALL shady… lol

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