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My Craziest Online Dating Stories

Updated on May 13, 2016
Surprisingly, this was not the movie we watched that night in the theater. It should have been, though.
Surprisingly, this was not the movie we watched that night in the theater. It should have been, though.
Also somehow seems appropriate.
Also somehow seems appropriate.

1. "Forgot-My-Keys-in-the-Valet-Box" Boy

One of my craziest experiences with online dating involved doing some risky things I'm not particularly proud of. Ladies: don't try this at home!

I met up with a guy I'd been talking to online for awhile. I'll just say his name was Nick (not his real name). So Nick and I met up one evening at a rather upscale Italian restaurant in L.A. Although he was a little shorter than his online profile claimed (supposedly he was supposed to be 5'5", but when I met him he was at eye level with me, and I'm 5'3"), we nevertheless had a good dinner and found that we had a few common interests to talk about.

So after dinner, not wanting to end the date just yet, we walked over to a nearby Coffee Bean and Tea Leaf and got a couple of caffeinated beverages. After a bit of conversation, we decided to walk across the street to the movie theater and see what was playing. Even though it was already around 10pm by this time, we decided to see a movie. It was a somewhat ho-hum rom/com featuring Katherine Heighl and Josh Duhamel.

By the time the film was over, it was midnight, and it was time for the date to end. Though I wouldn't exactly say sparks were flying, we both had had a decent time and enjoyed ourselves.... that is until....

Nick suddenly realized that the restaurant we had dined at was very closed, and the keys to his car had been locked in the valet box. His car was parked who knows where, and his keys were being held prisoner. I watched as he desperately tried to jimmy open the valet box to retrieve his keys, to no avail.

Thankfully, I had parked in a lot where you pay a small fee (I think it was $3.00) to park. My car keys were safely stowed in my purse and I was ready to go. But I felt bad leaving my date without his car or a way to get home. He also explained that he had to work in the morning and lamented that his house key was on his key ring with his car keys.

So, thus began a series of poor decisions that I'm thankful did not result in me getting hurt in any way... this is the part I definitely don't recommend.

First, I gave Nick a ride in my car. Never let a virtual stranger into the car with you like this (or get in the car with them). Secondly, I drove him to a couple of local hotels, to see if he could stay for the night. Unfortunately for him, there were no vacancies at either hotel that we tried.

Next, I finally offered to just drive him all the way back to his house (which ended up taking over an hour due to traffic from construction on the road. Yes, they love to do construction late at night, which is usually a good thing for most drivers, but not in this case).

Nick had remembered that he had left his back kitchen window ajar, and would be able to shimmy it open with some assistance. Once we reached his house, my next foolhardy (although, granted, it was in an attempt to be courteous) decision was to hoist him up (while wearing a dress and heels, mind you) to his kitchen window so that he could pry it open enough to get inside.

After such a crazy, unexpected (and admittedly, unwise) adventure, I finally got on the road home and my head hit the pillow wayyyy later than planned. Nick had a good laugh with a few of his co-workers the next morning, and was able to get his car back. After one more date, we parted ways, since like I said, the sparks weren't exactly flying.

Moral of the story: don't trust strangers, even if it's someone you think you *somewhat* know because you've been talking for a while. And whatever you do, don't put yourself in dangerous situations just to help someone out or be courteous. When it comes to protecting yourself, you have to do what it takes, even if that means appearing rude in the moment. Looking back on this night, I know I should have just said, "Sorry about that" and drove away. Nick was a grown man. He could have gotten a cab. Still, I'm thankful nothing bad happened and that this story has gotten a few laughs over the years.


2. "Stubby" (Otherwise Known as "Night Sweats") Guy

This guy, I met on the website He seemed like a sweet Christian guy, and was fairly handsome looking. We met up at a run-of-the-mill chain restaurant (I think it was someplace like Applebees, but I don't remember the exact name).

Before we even met up in person, though, there was one odd thing that stood out to me about him. He kept mentioning in our online conversations that he suffered from night sweats. Without knowing what to say, I just kept advising him to see a doctor (while laughing to myself because I couldn't help but find his admission a little bit funny).

When we met at the restaurant, he extended his hand for me to shake. Pretty typical. We sat down and placed our orders, and the conversation began to pick up. Suddenly, I saw a flash of something. He had brought his hand up from under the table momentarily, and it looked as though his fingers were missing from his knuckles and up on one hand. Although I was fairly certain of what I'd just seen, he quickly hid his hand underneath the table again, preventing me from knowing for sure. He spent the rest of the date hiding his hand, although I did not mention anything about it and tried to act as though I hadn't noticed. After all, I didn't want to be rude about it. What if he had been born like that? What if it happened in some tragic accident? The only thing I found odd was that instead of just addressing it right away, he attempted to hide it from me and not talk about it.

Also, one again, he brought up the night sweats in conversation, only this time we were face-to-face. "Have you seen a doctor about it?" I asked, feeling like I was playing nurse to him somehow. "No," he replied, and as he elaborated it seemed as though he was resistant to talking to an actual healthcare professional about it. For some reason, he just wanted to tell me all about it! "So, you feel feverish and sweaty, but its only at night, not ever during the day?" I probed. "Yes, exactly," he admitted. My goodness, this man needed to just see a doctor and get this issue resolved! It was obviously bothering him.

After finishing up our dinner, we walked around the shopping center and chatted. All the while, I made sure not to bring up his hand, even though the issue hung in the air as we walked (or so I thought). Finally, we concluded our date with a hug and went our separate ways. After a couple of brief online conversations, we stopped contact, but not until I stalked all his pictures with my roommate, scouring each one for the evidence of the mysterious hand. Sure enough, I could definitely see that my eyes had not betrayed me earlier at the restaurant. In a way, although my friends teased me and nicknamed him "stubby", I thought it was kind of sad. Not because he had a deformity, but because he felt like he couldn't discuss it and felt he had to hide it from a potential mate. If he had been the right one, I would not have minded in the least that his hand was a little different. Now the night sweats..... that might have been another story!

This is not what his actual car looked like, but it gives you an idea.
This is not what his actual car looked like, but it gives you an idea. | Source

3. The "Messy Doctor"

I met this guy on as well. We ended up dating for a month or two. For our first date, we met up at a restaurant. At some point, I ended up going to the house he lived in and meeting his roommates. He lived with a couple and their baby, along with another young man. They were all in the same program, training to become doctors. I thought it was really ambitious of this young man that he wanted to become a doctor. Things were going pretty well, until....

He invited me into his bedroom to watch a movie. His roommates jokingly warned me about his room, saying it was basically a pigsty. When I walked in, it was just that, plus it smelled to high heavens of body odor. Yuck!

Likewise, once when we were going to see a movie, I rode with him in his car, which was filthy on the outside. He explained that he had been very busy lately with his residency program (which I could understand). However, while driving around, he chastised me for even *looking* over my shoulder into his backseat... which was absolutely horrendous. Dirty clothes covered the seats, along with an empty pizza box, empty soda cans, and a whole assortment of trash... I was fairly horrified. I've been known to keep a few water bottles and trash in my car, but this was ridiculous! I even offered to wash his car for him, which he declined... The relationship fizzled out shortly afterward.

He didn't look anything like this. Except the cowboy hat.
He didn't look anything like this. Except the cowboy hat. | Source

4. The "Clammy-Handed Cowboy"

After meeting on an online dating website and talking for a while, this gentleman and I met up in the L.A. area. When I first met him in person, I was seated, and he walked toward me and extended his hand to say hello and shake mine. As soon as I stood up, it became clear to me that this young man had exaggerated his height on his profile (as so many people seem to do). We were virtually the same height, although his profile had advertised that he was taller. He was also wearing a cowboy hat and cowboy boots, although we were not really in the right venue for it (it's not like we were going line dancing that night or anything!) Still, despite not getting the whole cowboy-themed memo, I proceeded with the date.

Through the course of the evening, I realized pretty quickly that I wasn't really into this young man romantically. However, I felt bad, because he seemed like a nice person. So when he asked me if he could hold my hand, I said yes, for some odd reason... even though everything in me was screaming "no!" We ended up going and getting frozen yogurt, and then walking to a fancy bowling alley and just sitting there watching other people bowl (I don't know what that was about). While chatting we held hands, and it was very uncomfortable and awkward for me because his hands were really clammy... yet still I proceeded on, telling myself it was only one date.

Later that week, I received a phone call from him, and I tried to let him down gently and explain that I wasn't interested in him romantically. He proceeded to tell me that girls like me don't know what they want, that I would never find the guy I thought I was looking for, and that although I had no idea, he was exactly the guy I was looking for. Wow. Way to try and win me back by telling me I don't know what I want in a mate! Needless to say, we never spoke again after that conversation. Poor cowboy.


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