These 3 Epic Dating Fails Taught Me Priceless Lessons

My three worst dating fails can be your best protection from making the same mistakes.

Last updated on Aug 14, 2023

bored and exasperated woman toys with the straw of her drink Nicoleta Ionescu
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You're looking for love and have been putting yourself out there. Then, you happen to have a Saturday afternoon free. So you decide to go on a last minute picnic with a guy from match.com and the date turned out ... um, let's just say, "not well'.

The date was no picnic (except for the ants-in-your-sandwiches part). But don't get discouraged: Even the worst dates — the ones that have gone terribly awry — have hidden jammy sweetness in them. The trick is that the lessons to be learned may be buried deep down in the awful ant hill and require a little deep introspection on your part.

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Let me tell you about some hilarious dating fails that turned out to have a silver lining.

Three Epic Dating Fails and the Lessons They Taught Me

Dating Fail 1:

I had a date with a Playgirl model who he wasn't shy telling me all about his photo shoot... plus the fact he had no job and no car. That was the extend of his conversational skills. Needless to say, I was not impressed (although he must have had some kind of talent to get into a glossy magazine like that). I never saw his spread — nor did he see mine — but I had a very, how shall we say it politely, interesting time with him at our post-workout hot tub date. I did have the pleasure, I guess, (if you want to call it that), of watching him strut around like a peacock. Calgon, take me away. Please. Take me far far away. Now.

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Hidden lesson: Looks can be deceiving.

I need some conversational spark, and Mr. Peacock did not seem to have it with me. I was much better off knowing right from the start. Just because he looks like a model doesn't mean he's right for you. In fact, a research study has shown people, both men and women, are often more willing to lie to an attractive person in order to get a date with them.

RELATED: 8 Clever Ways To Ditch A Disastrous Date

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Dating Fail 2

There I was, on a first date with a handsome funny guy. We were having such a good time we decided to go to the movies after we shared our hot fudge and whipped cream. A movie theater isn't the best option for getting to know someone, unless you are hoping for some hanky-panky in between theater chairs with giant barriers. But, this is what we had decided, so off to the multiplex we went.

I held his arm as we walked into the theater. We marched two by two to the box office and standing right in front of us was... my ex-husband and his very pregnant new bride. Ugh.

We made awkward introductions and shuffled over to the concession stand. I felt relatively unscathed and very happy to be out of the situation. With popcorn in hand, we picked our movie and walked into a very empty theater — empty except for two people: My ex and his wife, of course.

Hidden lesson: Expect the unexpected.

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When you are dating, be prepared because you might just run into the unexpected and the uncomfortable. If you don't let it catch you too off guard, you can bounce back without missing a beat.

RELATED: 10 Worst Tinder Dates Ever (As Witnessed By Bartenders)

Dating Fail 3

I decided to meet a new man who understood the art of flirting with words. He had that whole "sensual subtlety" thing down pat in his sexy instant messages. We met in person, had great eye contact, good conversation and killer chemistry. Yet, I couldn't help but think about how I noticed his profile location had been changing from one place to another.

I mentioned this and he proceeded to tell me he was a manager of fine hotels and had to travel to different regions for his work. It made sense to me. We parted ways, but didn't kiss goodbye — he had also mentioned in our face-to-face conversation that once he kissed someone he "had" to finish with sex. (Say what!?) So not kissing on this date was a no-brainer.

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Several days later I was gave my girlfriend a ride to a not-so-nice local hotel. We were chatting as we turned into the hotel parking lot and discovered the man who I now call Mr. Clean. He was wearing not-so-sexy, long yellow rubber gloves as he pushed a cart filled with brooms, mops, disinfectants and trash bags with one hand. In the other hand, he wielded his trusty tool — a bristled toilet bowl brush.

Hidden lesson: If you tell a small lie, remember it's also a small world.

A little lie or a big lie will almost always be discovered. A good thing too, if he exaggerated his work and career, what else would he conceal or misconstrue?

Dating is sometimes like treading through shark-infested waters. The sharks may be rich, funny, sensual, handsome, chubby, rude, sexy, just plain clueless, or have bad taste. You never know until you get up close and personal. But the best part about dating is, even with dating fails, there is never a dull moment. There is always something to learn about yourself (and men) when you meet someone new.

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Every epic dating fail has a hidden lesson you can take away. You may need to have a session with your new dating coach (hello, I know a great one!) to find the golden wisdom deep within the disastrous date, because trust me, there was a lesson.

So, if you are single and confused about the fail filled world of men, dating, and love — and looking to find the right kind of man, don't be afraid to ask someone for help.

RELATED: Yikes! 5 Worst First Date Stories Of All Time

Dina Colada is an author, speaker, and dating coach who has appeared on sites like Prevention, Women’s Health, Plenty of Fish, and Zoosk. She specializes in helping single women navigate the modern world of online dating.

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