Dating Horror Stories

Dating Horror Stories

I’m interested in hearing people’s online dating horror stories. With a website called “Dating Online”, I certainly don’t want to scare people off from internet dating. At the same time, I don’t want people to think I’m some shill for the online dating industry, either.

Given all the “how to date online” and “dangers of dating” posts I make, readers probably aren’t surprised I’d introduce “dating horror stories” subject anyway. I think we might pick out a pattern in what to watch out for and what to avoid when dating online.

Bad Online Dating Stories

To get things started, let me relate several short online dating stories that I’ve learned either from friends or from reading about the internet dating scene. I’ve never had the really crazy personal online date or online relationship, but that’s probably because I practice all the dating tips I preach and therefore have kind of weeded out most of the real crazies from my online dating life.

Still, online dating is like practicing safe sex: you can do everything right and it’s not going to work 100% of the time. So with that rather graphic image in your mind, let’s move on to the online dating horror stories.

Online Dating Horror Story #1 – The Felonious Girlfriend

I knew a guy (Kevin) who met a girl online who actually lived within 40 minutes of him. They started chatting online and really hit it off. Within a couple of weeks, they had their first date and seemed to have romantic chemistry. The sex was great and they both seemed really into one another.

Against my advice, Kevin moved in with the girl within six weeks of their first meeting online. Rooming with your love partner is an amazing temptation, especially in a bad economy. Of course, he didn’t have the time to really get to know her, so he was setting himself up for a whole bag of surprises. That’s exactly what he got.

First off, Kevin found out she had a criminal record. Sure, that was supposedly in the past, but her family wasn’t in the past. Just like the girlfriend, her entire family lived in the area. She had two suspicious brothers and a sister who was always butting in.

This might have been understandable if this was just concern about their sister meeting some stranger and moving in with him immediately. But it turns out the family had huge interpersonal conflicts and loved to argue with one another, feud with one another and generally make each others’ life a complete disaster. These were the kinds of people who drive someone into a life of crime.

Even that might have been workable, except the girlfriend turned out to be the jealous, controlling type. In other words, she tried to drag my friend into her crazy, melodramatic world. The poor guy nearly lost his mind in the six months they lived together. Like he told me at the time, “The sex is great. Everything else is a nightmare.”

Dating Lesson: Don’t move in with someone too quick, especially if you didn’t know them before you started dating. It always amazes me that people hate blind dates, but they don’t mind blind relationships. That is, they’ll just move in with whoever they’re dating at the moment with no regard to what that is going to do to the relationship. Instead of getting to know one another a bit at a time, you’re in one another’s face 24/7. Bad idea.

Online Dating Horror Story #2 – The Narcissistic Boyfriend

Just to show that it’s not all about bagging on the women in our lives, let me tell you about me friend Jamie. Jamie is a sweet girl, but she seems drawn to the wrong type of guy sometimes. In this last case, she ended up dating a narcissist.

I’ve often mentioned that women like confident men, which can be a real shame, when they meet up with a narcissist. Jamie met this guy who was brash and confident and would tell anyone about his success and his life.

Jamie assumed he was just a guy who wanted to impress, so she gave him a chance. They had several of the same interests (dancing, water sports, blogging), so she thought he was worth a date.

Unfortunately, the Narcissist was simply constitutionally incapable of talking about anyone but himself. He would drone on and on about his jet ski, his blogs, all his “hot” ex-girlfriends. On the date, he simply would not ask Jamie about her life and her interests, as if she was only there to listen to how great he was.

In fact, when she interjected to take subject off the Narcissist, he would look bored, then raise his voice louder and louder, drawing attention to himself. It was obvious this guy wanted attention, no matter how he got the attention.

Well, it was obvious to those Jamie told about this date, but not necessarily Jamie. I mean, dinner conversation sucked, but he can’t talk over the dance track or a jet ski (well, kinda the jet ski, when you’re riding two-on). But there was enough slack time and enough activity that Jamie, knowing that she didn’t want any part of this guy, decided to give him a second date.

This one was more traditional, and more disastrous. She found that he wasn’t trying to impress her – that’s just the way he was. On his second date, he was even worse. Once or twice, he compared Jamie unfavorably to one of his recent ex-girlfriends. Jamie knew this would be the end, or at least she thought it would be.

Wait a month or two, and suddenly the Narcissist calls her one night – drunk. He’s ranting about some new ex-girlfriend, then asks Jamie out again. This happened several times over the next few months, because a narcissist can’t imagine a women doesn’t want him around.

Dating Lesson: If a guy seems full of himself, he is. If a guy isn’t interested in asking you questions about yourself, he’s not really into you. The same goes for guys dating a girl. When they don’t seem interested in learning about you, that person has some motive besides establishing a real relationship with you. It’s as simple as that.

Internet Dating Horror Story Submissions

Anyway, there are two online dating horror stories. Looking back, the first story is actually more horrific than the second.

Kevin actually ended up living with a psycho. Jamie just wasted a few nights of her life with an out-of-control egomaniac. It’s not illegal to be a narcissist, and she did get some water sport and a little bit of dancing in, so it wasn’t a complete horrific mess.

But I’m sure there have to be a million dating horror tales to tell. So let’s hear them.


  1. renee harmon says:

    I was looking to meet and date only one man. I was ignorant about online dating. I thought that if I opened a profile, I’d meet a guy that was nice, normal and healthy. After spending an hour looking over profiles on the first evening I found one guy that seemed to fit everything that I had wanted in a relationship.
    On the first night we talked for about two hours. He said he felt he had known me all of his life. Common response I suppose when you feel that you have non-stop conversation. We agreed to meet at a local Starbucks the next evening. When I arrived his eyes opened wide. He would later comment,”I hadn’t imagined you would look this good being on a dating website.”
    Fast foward a week later. We were spending every moment together. We took many local trips, had so much in common and lived five mins. apart. He showered me with compliments and I was so happy to meet a man who was into me as I was into him. This elation created blindness. I was so happy to meet this guy I didnt’ consider his phone going off all evening to be other women calling him.
    I would learn after five months of dating him he would make subtle confessions like,”I gave up my freedom for you,” ” do you think that all those calls were from my guy friends,” to “I just want to concentrate on school.” I also learned from a family member who really had grown to like me that I was the first girlfriend that he had ever brought to family functions and that he met girls on dirty websites that give a one night hookups.
    After looking back it all made sense to me. He wasn’t new to online dating as he had claimed when I had met him that first night. He was addicted to what I call “gross misconduct” in a relationship. He had the wrong motive, in other words he thought he was ready for a committed relationship but the years of addicted dating to one night stands had given him the idea that when you don’t like something about someone you throw them away. He didn’t have a realistic grasp about what real relationships required. Instead in his one night romps he had mistakenly adopted the view that the diversity, ordering online sex by the click of a button, and instant romance was something that wouldn’t haunt him when he thought he was ready to retire his destructive ways and settle down with a decent woman.
    While we were dating he could only look at how much freedom he had lost by trading them for me. In the end, I was devastated to learn that he didn’t want me; he wanted variety. It’s still difficult to comprehend, especially when I was a very devoted, sensual, and a good-looking woman. I guess it goes to prove that when a man has spent years of irresponsible dating, he is very irresponsible in a relationship. He won’t change, until he changes the root of the problem. This was a lesson learned a bit too late.

    • Renee

      I hate to hear about your heartbreak. People have to want to change. People that don’t change, prefer being the way they are. That’s harsh to say, but true.

      Don’t give up, though. One example does not make the race. “Single guys who date online” are not all like this one man you dated. In my experience, there are a lot of good guys out there who want nothing more than to find a nice woman and settle down.

  2. I went on an internet date to a nicer restaurant and within the first few minutes this lady was very bold in stating that the only reason she was doing this was to get married and she needed a shot of Tequila.
    Down the road I went. WOW, at least she was honest.

    • Joe

      You just wonder why she thinks that’s going to attract a man. You’re right, though; I guess you can’t fault her honesty.

  3. Paul D. says:

    For over 3 years I knew this woman online that had become a close friend. For the sake of this reply I will simply call her . I thought of like a sister and whenever either of us had news to share, whether good or bad, we would always be sure to include each other. We were friends during particularly tough times in each others lives.

    At one point introduced me to a good friend of hers, who I will call here. was a much younger woman (I was 48 and she was 22) but seemed very together and mature. She was also a vibrant person that made every conversation a pleasure. I was surprised and reluctant to get involved when indicated that was interested in me, but managed to calm my anxieties. It was the first time I ever considered a lady that much younger but it was like was made for me in personality.

    The online relationship lasted for 9 months. In the first 3 or 4 months I couldn’t travel to due to personal and professional issues. Once those issues were resolved, could not travel as she was caring for a terminally ill friend. Even though the emotions and the relationship grew quickly, we never got to meet. talked with me about not just getting together but starting a life together and I was all to receptive to the idea.

    After the holidays, the other shoe dropped. sent an e-mail telling me that and her terminally ill friend were in a terrible car crash. He was killed instantly and was in a coma. would not tell me where and would not let me come to visit as had never told her family about me.

    I respected ‘s wishes in the matter and did not go there, but as time went on information started to come less and less frequently. Remember that was someone that had professed a committed exclusive relationship with me and wanted to move into a more mainstream ‘in the flesh’ life together. I had taken at her word and this situation was hell for me.

    I finally realized something was very, very wrong when I tried to get to see how I felt by asking what if it were her husband & she couldn’t see him. went absolutely ballistic on me. Her reply was quite cruel and agressive and ***finally*** I realized that I was being manipulated, not informed.

    I went online and researched everything I knew about the accident and found nothing. An accident that size should have had some kind of report online. It involved a drunk driver, an airlift rescue, a serious injury, and a fatality. Next I checked the information I had on and . Considering the length of time I knew them and what I thought were deep relationships, it was a complete surprise that nothing about them checked out.

    At that point I made a decision that I hope I *never* have to again. I hired a PI in their area to verify the situation and see if was alright. It was a tough choice, but I needed to know the truth so I could move on. I provided the PI with everything I had including all the pictures that and had provided. It took months, but the PI finally found .

    As it turned out, wanted an online fling and this is how she went about it. used pictures from God knows where to be the face of , but from the volume of them she had to know the woman. When had her fill, she made up this soap opera fiction. I am more at a loss for why end it in the eternal hell of a coma that just keeps lingering. If she had told me died I would have at least eventually found some peace in it and moved on.

    I realize now just how gullable and stupid I was for simply accepting every excuse without question. All and all I am lucky something worse did not happen. Beside learning that trust is something that needs to be *repeatedly* earned on the net, I did learn that the heart is far too valuable a resource to be given foolishly.

  4. Paul D.,
    Thanks for your honesty in feelings on your post. I can see how much sadness this could create and its a hard lesson earned indeed. I think that the lesson is, as you alluded to, is that though the web is a useful tool, it also adds a sense of superficiality that can be easily disguised. I think it is hard to trust the person without seeing the face with its expression and clues that could be your guide.
    I am in my 40’s and personally would have been suspicious in the makings of a relationship with an early 20’s woman. There is too much uncertainty and unpredictability at that age for a long distance commitment. Im sorry that you led your heart into it, and I suppose that years of confidentiality shared over 3 years via email formed that bond.

  5. noconsent says:

    Some women are addicted to online attention

    Seems like the internet destroys morals in some women an example is the last girlfriend i had.
    i met her at a free online social network which she calls it and always made me laugh. social and dating is two different things but since the invent of ” the social network” dating is not dating its making friends that want sex , times sure have changed .Back to my story, she was a great gal we meet had dinner and drinks i thought i hit the lottery then the other shoe dropped. She started talking about her “married friend” she met at same “social network” . then on my first visit to her home her live in brother who is a 40 year old ex con that dont work , she pays his cell phone , he dont pay her anything to live there . She cooks and cleans for him and buys food already scary huh?. Well he shows me his new tattoo which says pray across his wrist then goes over some married womens house he has been screwing when her husband leaves. That night her and i have sex but she has to keave the bedroom door open which kind of creeped me out since her brother was back and upstairs , the stairs ending at her bedroom. The next morning i have to listen to his brother making jokes about hearing his sister and me talk about awkward.
    Now both shoes fall a week later she shows me another web site she is on married date link her name friskyfeline. Holy cow first her brother then her both screwing around with married people. She told me about the great people she met there and her friends all married guys of course lol. I told her that will cause some major trust issues so after about 4 months she said she understood and stopped going there but forgot to tell me she moved her married date link friends to her facebook YIKES!
    Now its over but fater a lot of breakups and getting back together with every breakup a new guy from her either married or single on the internet.
    My advice to anyone doing online dating to get serious and if you do check the computer out odds are there are other guys she is talking to

  6. I’ve had two life changingly bad experiences with online dating. I didn’t seem to learn after the first mistake.
    I went on a dating site for people with a certain mental handicap. I won’t say what, but think along the lines of ADHD. Now, I don’t have said handicap but I tend to connect with others who have that issue – I seem to relate to them the most. Well, I had been talking casually to a decent sounding guy, fairly attractive, and just out of the marines. He liked taking psychedelics, reading about math, studying Physics, ect. I enjoyed chatting with him until he became annoying and started sounding just bizarre. I had no intention of meeting him until I found out he was going to college in my state.
    I was 17 and knew it was stupid to meet with someone online before you are an adult. So, right before my 18th birthday he tells me he is in Wisconsin. I reluctantly agree to go on a date with him. We met the night of my birthday. I thought it was cute that we had the same quirks, such as, arranging the silverware in perfect angles at the restaurant and the fact that we were both shy. The attraction didn’t go farther then that and since I have a hard time saying “No” I agreed to continue meeting him – I mean, why not? I found out that he was living in his car in the city. He wasn’t enrolled in any college. He managed to use people and a disability check to move into the basement of a public building where I spent many nights listening to him scream. He would scream extremely loud and randomly. He would talk about these “dark images” he had in his head and we would take drugs I’d never heard of. It was “fun” and all until he began speaking violently about things like torturing women and killing dogs. My favorite quote by him is “I don’t get an erection while watching porn but if I see a mangled dead woman I get a huge hard-on” There was a time where he was violent during sex. He was stronger then me and held me down, hurting me, and listening to me scream in pain. I had dark bruises all over my body after that.
    He bought a huge knife. I was literally frightened of breaking up with him because he’d talked about being together forever and I went through 5 months of hell being scared of him, but unable to leave because I thought he would harm me. When I broke up with him he cried and cried. I walked to a friend’s house and got a ride home. To this day he still sends me emails about wanting to skin me and leave me alive. He has MAJOR issues and it’s left me sleepless knowing that he knows where I lived…

    Anyway, this next guy ruined my life to this day, in a nut shell. I was just turning 19 and met this really sweet, attractive guy online. He was 50. The age difference never bothered me because he was a sweetheart – very shy and talented. I promise you, I was not looking for a Sugar Daddy and he was not looking for a “replacement daughter” – We just had alot in common and were attracted to each other. The date was perfect and we had good conversations. It was like I’d met the perfect guy and he’d said I was his perfect girl. I was in a relationship at the time, but broke up with him because I thought this new guy was something special. That night we did end up having sex. He told me he “loved me” that same night which I kinda just rolled my eyes at. Lust is a powerful thing. Early on in the relationship he would talk about going to Europe and getting married to me, his soul mate. Within a few weeks I was convinced he was my soul mate – All the signs pointed to it and I musta been delusional! I moved in with him WAY TOO early, thus, ending my Father’s trust in me. Because he lived farther away from my job, I had to quit so he wasn’t getting up early to drive me around. He wanted me to drop out of college to start my own art business and I did (the business never went anywhere). We lived together happily for about a month and a half. Then one day he was getting ready to go out and just said he wanted to end it. I had dropped everything in my life for him. My family, my boyfriend, my job, even my art. I begged him to stay with me – I had nowhere to go. well, we went on “happily” except, he never took me out anymore. He rarely wanted sex. He never kissed me. He seemed annoyed by little things. I did everything I could to be charming and pleasant for him. I found out the reason he broke up with me was because his friends and sister was ragging on him about the age difference. If we were “soul mates” then age wouldn’t have been an issue! I feel cheated a bit, because the beginning of the relationship was promising and he didn’t doubt us as a couple at all. Long story short, he recently kicked me out. …. Now I am still unemployed and have nowhere is stay except with my father, and I don’t think he’s too fond of me. Anyway when I said I gave up everything for this guy, I meant it. It was half his fault for leading me on and half mine for being stupid enough to fall for him.

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