online dating stories

Let me be the first to tell you that online dating works. It gives you a fantastic way to meet new people that you likely would have never met otherwise. When I was on the prowl I found it difficult to meet new and interesting individuals. It seemed I would only meet people at a bar or club, and let’s face it, that is probably not the best place to meet someone if you are looking for a serious partner. I’m not saying it’s impossible, it just wasn’t for me. I met a lot of genuinely interesting and nice guys along the way while online dating, so please don’t let this article give you the idea that everyone you meet is a complete bozo. On a separate note, be prepared because you will encounter some bottom of the barrel people. I don’t think I have met anyone who emerged scot-free, not even my husband who I met online.

I found out quickly that among my circle of friends and coworkers, I was the girl with the fun and exciting online dating stories and everyone always loved to hear them, especially if they were horrendous. If you run into an extremely awkward situation, at least know you will be left with a story to tell. I’m going to share with you my top 5 craziest online dating stories in sequential order.

Fetishist in disguise

When I finally made the plunge to start an online dating profile I was excited and nervous at the same time. Did I choose the right platform? Do I sound interesting enough? What the heck are my hobbies? Does this picture still look like the current ‘me’?  I spent a bunch of time making sure that my profile depicted the true me, or at least the me I thought I was. There was one guy from the first set of inquirers that I found interesting.  After a series of messages, we exchanged phone numbers to begin texting.

We held a text conversation for a day or two. I looked him up on social media to see what he was about. This was it, my first online date! I was particularly nervous. You hear all the horror stories and I had no idea what to expect or what the norm was, or where to even suggest going or when. I decided to plan to my comfort and suggested a lunch date. My thought process was, I would let my coworkers know where I was going and why so that if I didn’t return they knew the details and could contact the authorities. Yes, I am a bit paranoid when it comes to that sort of thing. Better safe than sorry, right? Well, I meet this guy for lunch. He seemed nice enough. He owned a small construction business, fished and hunted. You know… the typical alpha male hobbies. We maintained an interesting flow of conversation for the duration of lunch and parted ways. I returned to work and filled in my coworkers on the details of the date. Overall, he was nice, non-threatening, and steadfast on paying for the meal. I’d say my first online date was a success!

Later that evening, we continued texting and things took a very steep turn. I don’t know what prompted this turn, but oh my goodness, turn it did! He went from a nice guy to a sex obsessed, hormonal, teenage boy. We went from talking about fishing stories to him telling me he has a fetish for panty hose and lingerie. I tried to side skirt the conversation and bring it back to a more appealing topic for having just met him, but my attempts were useless. I remember thinking to myself, “I guess this guy wants to lay his cards out on the table so he doesn’t waste any time”. I just stopped replying, put my phone on silent and went to bed.

When I woke up there was a slew of messages from this guy. They continued with all his sexual desires. Please let me remind you, I did not ask, nor did I want to know any of this. I just met this guy! Following all that I saw that he sent some pictures. Oh dear the pictures. I can honestly say in my entire time dating this was the only time my eyes were scarred quite like this. They were pictures of him. In all of them he was wearing panty hose and women’s lingerie. Yup. Not kidding. To make things even more disturbing, in 90% of these pictures, he also had items in and around different orifices. As if that wasn’t enough, following these pictures were really mean messages. I guess his ego got hurt that I didn’t immediately reply with enthusiasm. There were messages about how I was a c*** because I was so closed minded, followed by I could never sleep with you anyway because you are way too fat, followed by you can delete my number. Delete his number I surely did! Keep in mind; this was my first ever online date! Yeiks!

RELATED:  11 Pitfalls of Dating a Younger Man

The 40 year old virgin

I don’t think of myself as being superficial but I have a thing with height. I am fairly tall and I feel uncomfortable with men who are the same height or shorter than me. Well, I matched with this guy who was a bit under my height standards but seemed pretty nice on paper. We exchanged numbers and decided to go out for a drink. The first meeting went alright, but goodness he was so nervous the entire time! His nervousness was just radiating off of him. We had a lot of similar interests so the conversation was pretty good, but as I knew I would be, I was a bit uncomfortable standing next to him because of the height thing. We parted ways but continued texting on and off for a week or two. I then decided to give him a second try. I was thinking maybe he wouldn’t be so darn nervous on the second date.

We met up for dinner and once again Nervous Nancy was sitting across the table from me. I didn’t know what to do to try to make him feel more at ease. Following dinner he walked me to my car which I thought was a nice gesture. What I didn’t know is his sights were set on a goodnight kiss. We arrive at my car and I am fumbling in my purse for my keys and he leans in to give me what I thought was going to be a hug. Well, I turned my body to return the hug and to my surprise he proceeds to make an attempt to kiss me. Let me tell you, there were no warning signs this was about to transpire. It was a stun, better yet a strike. His head rapidly moved toward mine but there was a major problem. The problem had nothing to do with me wanting or not wanting to return the kiss, heck I had no time to decide that at all because it was so abrupt. The problem was that he was coming at me full speed, with an open mouth. What the heck? Who does that? So here I am standing next to my car expecting a hug and instead this dude is throwing a speedball kiss my way and when his lips land, they landed on the outside of my mouth. You know the lip skin below your nose and above your chin? Yeah that’s where his open mouth landed because my lips were sealed. He dwelled there for a second with his eyes closed and I was just wide eyed thinking what the heck is even happening right now. When he pulled back there was saliva on the outside of my mouth that I had to wipe off. At that point, I knew I just experienced the most awkward kiss in the history of my life and I wanted to get the heck out of there. I said goodnight to him and hopped in my car to head home.

On my way home I received a text from him saying he really enjoyed the date and can’t wait to see me again. I obviously had very different feelings about the night’s events. Later that evening he decided to send me some pictures of the Lego sets he was working on. That’s when I knew. The nervousness, the viper kiss, the Legos…. He was the 40 year old virgin.

The enthusiastic loud talker

This date was a far-fetched one from the start. We arranged to meet at a restaurant between our two homes. We did this because he lived so far away. In hindsight, how that would have worked, I don’t know. I arrive and meet him just inside the restaurant, and immediately I realise I am extremely underdressed. I was not aware this was a white tablecloth type establishment, and here I am wearing jeans! Thank goodness I was wearing heels and a nice blouse to make up for it a little bit.

RELATED:  10 Powerful Tips For Creating Your Online Dating Profile

My date was very polite and extremely friendly which was refreshing. We were seated at our table. This restaurant was very nice. The menu was amazing with French cuisine and delicious and uncommon ingredients. We decided to split a bottle of wine. I could already tell this guy liked the finer things. This life would be new to me. I am about as frugal as they come. Rather than foie gras, words like reuse, recycle, coupon and save are more commonly used in my vocabulary. Nonetheless, I tried to thoroughly enjoy myself. My company was great minus one major thing. He was so loud. I mean like the entire restaurant could hear our conversation. Every joke, every life story, every aspiration and dream told, the entire restaurant knew about it. I was extremely embarrassed at first. People who are truly trying to enjoy a fine dining experience are turning a staring at our table with snarls and I was genuinely mortified. Thank goodness my jeans were mostly hidden beneath the white table cloth, or that would just be icing on the cake! I proceed to drink my wine at a very unattractive rate to try to ease the feeling of the judgmental glares we were receiving from the entire restaurant. I thought to myself over and over, why is it that they couldn’t have seated us in the very back of the restaurant. At least then the front of the restaurant could almost enjoy their meal without this guy’s loud mouth disturbing them. He was at least genuinely funny. He had me laughing my head off. Even with that, he laughed at his own jokes and his laugh was more of a roar probably heard outside the restaurant walls. Needless to say, I was more than happy to get out of there.

Wannabe Aziz cop

I went on a date with a cop, and boy did it change my opinion of the type of people in law enforcement. If only there could be some sort of character check or something. Sure I know not everyone can fall in the same category, but it definitely makes me leery. A title does not equal trust. Let that be a lesson for all of you out there as well.

I go on this date and it starts slow. It was like digging for conversation at first. It felt as if he was almost uninterested in the date, which is an awkward feeling. I have to admit, at this point I had very low expectations of the men I was going out to meet. I had talked to and been on quite a few dates where I had my hopes up and they ended up being big fat no’s. I learned quickly it’s better to have low expectations and be surprised. After all, part of the adventure is having new experiences and meeting new people. Not everyone is going to check all your boxes. After he had a drink in him, he lightened up and became more talkative. He began telling me some stories about his daughter, some goals and aspirations he has, and some stories about being on the job. This is when I started to question his character. He told me several stories where he blatantly abused his position as a police officer. I don’t know if he thought that was cool or made him look like a rebel or something but in my eyes it was not cool, it was not attractive, and it was downright alarming.

It came time to leave the restaurant and walk back to our cars. His car came before mine on our walk so I figured I would just say goodbye at that point and walk to my car alone. We went in for a hug, but he was giving off all the signs that he wanted a smooch, and honestly I don’t know why but I allowed it. I guess in my head I was thinking, what harm would a little goodnight kiss be?  He proceeds to kiss me, but then it turned very quickly to him grabbing my hips and pushing me against his car. Just because I gave my consent for a harmless kiss did not mean I signed up for that! I very clearly made moves to break out of the situation, but he did not stop. Instead he proceeded to try to put his hands up my shirt while rubbing his blood engorged nether regions on my leg. I started feeling nervous. No. Actually I felt scared. I mean this guy is a cop. He just got finished telling me stories where he blatantly broke the law and got away with it because he is an officer. He was the law, and I guess in his eyes that meant he was somehow above the law. All this happened in a matter of seconds. It’s like he planned on this from the start, or literally couldn’t stop himself. He certainly was not reading my body language and most importantly was not even considering if I was a willing party. I had to writhe my body and push away from him with all my strength to get him to stop! I mentioned that I had been on many dates and not one of the others did anything like that! Heck I didn’t even think the date went very well. When I finally was not between him and the car I wiped my mouth with a scowl on my face and said, “We are done here.” I hastily walked to my car while keeping my sights on my periphery and digging in my purse for my pepper spray. As soon as I got in my car I locked the doors and waited for him to leave the parking lot. There was no chance in hell I was going to risk him following me. I even looked up where the closest police department was just in case he did follow me.

RELATED:  Why Keep Dating Mr. Wrong When You Know It Isn't Right?

Going back to my original sentiment, a title does not equal trust. Don’t let your guard down.

I forgot my wallet guy

I made plans with a guy to meet up for dinner. As time grew near, he sent me a text sounding very apologetic. He said his car was in the shop and he either wouldn’t be able to make it tonight or if I didn’t mind, could I pick him up. Well, that was a very strange request, but I also know sometimes things happen that are out of your control. I bit and said I would pick him up. I asked where to pick him up. I’m thinking it’s going to be at his apartment or maybe his job, but no. He asked me to pick him up at the mall. Weird, I thought. Anyway, I go to pick him up and when I see him I roll down my window and asked, “Where ya headed? You’re not going to show me any leg?” I thought treating him like a hitch hiker would be a fun ice breaker. It was. It took a little bit of the awkwardness away.

We went to the restaurant and had a good time talking. Had a couple of drinks. Overall it wasn’t a bad date. I found out a bit more about him. He was a chief in the navy and had seen many places around the world. He had lots of fun stories to tell. Right before the check came he tells me that he forgot his wallet. I’m like, really? That’s an odd thing to forget when you know you are going on a date at a restaurant. I am not the type that expects anyone to buy me a meal simply because I am a girl. I prefer to be treated as an equal. I always offer to pay or at least pay for my half, but this was just off-putting. The bill comes, I pay for my meal and my one drink along with his meal and his four drinks. Hmmm… Seems very odd to be willing to rack up such a bill knowing you don’t have your money with you. I paid. I wasn’t sure what else to do honestly. I thought about leaving him at the restaurant and letting him figure out how to get home, but I am too nice of a person. I decided I would drive him home. He gave me directions as we drove, and when we arrived at the final destination, it was a bank. It was not an apartment or a house. It was a bank.

At the end of this evening I was left wondering, did I just pay for a homeless guys dinner and drive him around town? What in the world?  Was he even in the military? Is my entire life a lie? Is the earth even round? No but really, what a weird date that was!

Amanda is a mechanical engineer, wife and soon to be mom from Virginia. She enjoys a good laugh, DIY projects, and new experiences. She is the writer of the blog An Inspired Mama.

Subscribe To Our Newsletter

Be the first to get the latest updates and exclusive content straight in your inbox!