Giving online dating a shot takes some serious guts and these folks had some high hopes after connecting with people via chat. Unfortunately, their dates turned out to be completely different in person and made them have the most awful time. From being catfished to stolen from, these people have seen it all! These stories just might make you second-guess online dating. This content has been edited for clarity.
The Wandering Hand
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“I’ve only had one negative experience through online dating. I was contacted by a young blonde who seemed to be right up my alley. We sent a few messages back and forth and finally set something up. I worked at a mall so we were going to meet for coffee followed by a movie after my shift.
I didn’t notice her walking up to me because she looked nothing like her photos. She was much shorter and had a ton of eye makeup caked on. Her nose looked like it may have been broken and poorly set. Really, I just had zero attraction to her. She immediately gave me an overly familiar hug and said,
‘You are so HOT.’
I basically spent the entire time at the coffee shop attempting to conceal my disappointment, but I’ve been on some lackluster dates before. Just put your head down, get through it, and move on. Afterward, in the movie theater, she started the wandering hand routine and I was giving her no positive signs whatsoever. She just kept trying and eventually started moving her hand from my knee to my inner thigh until I finally rebuked her.
When the movie ended, she asked for us to go to dinner. I claimed to be short on cash to get out of it but she said she’d pay since I had paid for everything earlier. I was tired from a long shift and trying to stay awake through the movie so I couldn’t come up with anything else. We grabbed a burger and had small talk, mostly about her cat, which she had been talking about all night.
When the check came, she grabbed it, took a glance, and slid it back to me. At that point, I just wanted to wrap it up and go. So I paid the check and drove her back to her car. I pulled in and give her the awkward hug and said,
‘Well, see you later.’
‘Hold on, I was going to ask if you wanted to come back to my place,’ she replied.
‘I don’t think that’s a good idea,’ I said.
Boom. Waterworks. She basically sat in my passenger seat, bawled her eyes out, and sobbed in broken incoherent sentences for the next half hour about how into me she was and about how no guys ever wanted her. I ended up convincing her I would totally call her, pinky swore, and she got out. I took off and never spoke to her again.”
Lesson Learned
“I was new to the online dating scene and tried out a dating app. This one guy messaged me asking very probing questions about the state of my teeth and specifically how I took care of them. He said he was a dental student and asked things like,
‘How many cavities do you have?’ and ‘Please specify the location of each cavity.’
I answered him because I was bored with nothing else to do. He then asked to talk to me on the phone instead as he hated texting and typing. He said he liked to call daily and talk for at least an hour. The guy had a bad vibe about him. His profile had no picture or age but I was very oblivious to the worst outcome if I agreed to meet up with him.
He was very persistent about meeting up and I agreed because I give in easily to peer pressure, so we went to get pizza in the city. When I walked out of my car, an older man greeted me. He had to be in his 40s, wore baggy clothes, and was bald with a baseball cap. My intention on the dating site was just to make friends because I was new to it all and wanted to go slow.
The man started talking about how we’d have a great time in bed and how wild he was. He said we’d do it daily multiple times a day. I asked him why he wore a hat and when he removed it, there was a huge lump on top of his head. He said it was a cyst and he was too scared to get it removed, but it looked like a horn. While eating, he would not stop talking about what he was going to do to me and it creeped me out so much.
After dinner, he had to drive me back to my car because I hadn’t known where to park. He wanted to inspect my teeth before I left. I said no thanks but he firmly insisted in a way I couldn’t refuse. He put on some purple gloves, and a headband lamp, and took a belt of tools out of his glove box. I thought that was when I was going to die. He used all the tools and took pictures of my teeth so he could ‘use them as an example in class.’
Before I left for real, he asked if we could make out. I lied and said I had a boyfriend but he said our relationship would be much better since he was experienced. I just ran to my car and dashed away as fast as I could. He was full of himself and was 42 while I was a timid 20-year-old. From now on, I demand a face picture before talking and I’m cautious.”
“I Know What You Are”
“While recovering from a nasty breakup, I decided to give online dating a try. A couple of weeks after signing up, I received a message from a guy named Justin. He was cute and just my type so we set up a date. We got along really well in person and ended up going on a couple more dates. It seemed like everything was going well.
Justin lived a ways away and it was my turn to drive to him for a date. We headed over to Dave & Busters and had a great time playing air hockey and Dance Dance Revolution. Then we decided to head back to his place to watch a movie. We’d kissed a couple of times and Justin was an excellent kisser. I was looking forward to cuddling and more kissing.
Before getting to his place, we decided to make a stop at Seven-Eleven for some snacks. We gathered up a couple of sodas and some candy and took them up to the register.
‘That’ll be six dollars and sixty-six cents,’ said the cashier as I pulled out my wallet to pay.
Justin gasped loudly and exclaimed, ‘We can’t possibly leave the total at six sixty-six! That’s the mark of the devil!’
I just laughed.
Justin got a very serious look on his face and said ‘If we leave the total like that we’re gonna get in a car accident on the way home and die!’
At that point, I felt he was being ridiculous.
‘Fine, grab something else if it bothers you that much,’ I said.
He threw a York Peppermint Patty on the counter and was satisfied when the total changed.
We picked out a movie when we got back to his place, we grabbed our bag of snacks and plopped down on his bed. I proceeded to take off my shoes and get comfortable.
Justin gasped again, ‘Oh. My. God. Are those the socks with separate toes? Those really freak me out!’
I looked down at my striped toe socks. How could anyone be freaked out by something so goofy?
‘Seriously,’ he said, ‘I can’t handle those socks. They really, really bother me.’
I just looked at him and leaned back on the bed. I was already over it. Little did I know, Justin was just getting started.
‘Oh my god,’ he exclaimed.
I could see a light had just gone off inside his head.
‘I get it now,’ he said. You’re a witch! It all makes sense!’
‘Come again?’ I asked.
‘It all makes sense: your black cat, your love of bats, your stripey witch socks, and you weren’t even bothered by the gas station total. Are you a witch?’
‘Get real,’ I said. ‘I’m not a witch.’
But I could see he was serious.
‘Well, I think you’re a witch,’ he said. ‘And can you please take off your socks? They’re really bothering me!’
‘I’m not taking off my socks,’ I replied. ‘You’re being silly.’
‘I can’t help it. Those socks really freak me out. I’ll do anything for you to take them off. I’ll pay you to take them off. Any amount.’
‘You’ll pay me?’ I asked.
‘Yes,’ came his reply.
‘Fine. Pay me six dollars and sixty-six cents’
He glared at me as I packed up my stuff and left. That was the last I ever saw of Justin.”
First Date Nerves
“The receptionist of one of my clients begged me to meet her best friend who just moved to LA from Phoenix. She swore up and down we were perfect for each other. I checked out her dating profile, chatted back and forth for a few days, then talked to her on the phone. We decided to meet for dinner and drinks at a local bar and grill after her shift on Tuesday night. We met and she was adorable: petite with dirty blond hair, glasses, and freckles. Totally my type.
I could tell she was a bit nervous while we sat down and ordered drinks. She downed her drink in less than five minutes, ordered another, and apologized, stating she wanted to loosen up a bit as she was nervous since her friend ‘talked me up’ so much. I thought that was odd since I don’t even know her friend well at all. Fast forward a bit and she ended up finishing two drinks before the appetizers came, two more in between appetizers, three more during dinner, and one right before the check came.
Total drinks had by a 5’3″ petite girl in a three-hour period: seven. Surprisingly, the conversation during that period did quite well. The trouble came as we were about to leave and she decided to use the restroom before we hit the road. She fell twice on the way and once on the way back. Since she was clearly hammered, I offered to drive her home and give her some cash for a cab in the morning to pick her car up. She agreed but declined the cash. Mind you, it was nearing midnight and I had to get up at 5:30 am for work.
As we were driving toward her apartment, it became apparent that, combined with her inebriated state and the fact she’d lived in the valley less than two weeks, she forgot her address AND how to get herself home. We drove around North Hollywood and Studio City for an hour trying to remember her street or any local landmarks. That failed and I was getting tired and frustrated.
I offered to let her stay at my place and said she could crash on my bed and I’d take the couch. She was okay with that. On the way back to my place, she attempted to throw up out of the car window but didn’t realize the window was never open in the first place. There was vomit everywhere and she was crying and apologizing like crazy. I got her to my apartment, carried her up three flights of stairs, and tossed her on my bed. She was out cold.
I went downstairs and spent 40 minutes cleaning out my car and finally got to sleep on my couch around 2 am. Around 4:30 am, I woke up from a shrill scream coming from my bedroom. I ran in wearing just my boxers and flipped the light on. The girl paused for a second, started screaming more, backed into a corner, and threw my nightstand lamp at me while yelling,
‘Who are you?!’
It took a minute for me to calm her down, explain the situation, and remind her of our night. It eventually all came back to her. She started crying and apologizing. After I calmed her down some more, I gave her a ride home.
During our ride home, the awkward silence is only broken by her apologizing while sobbing, telling me how to get to her place, and then asking if we hooked up. I told her we didn’t because I’m not the creepy type to take advantage of girls in her condition. She replied with something along the lines of,
‘Oh. Okay. I’m not typically a lush and I’m definitely not a tramp. I was just super nervous and didn’t know my limit last night. You seem great and I hope we can see each other again.’
I ended up saying ‘sure’ just to avoid any more awkwardness, gave her an in-car hug, and said goodnight. The next day, while slothing around work in a meeting, she called. It went to voicemail. Immediately she called two more times and finally left a voicemail. Said voicemail went something like this,
‘So I was thinking about what I asked you on our way home last night in regard to us hooking up. I’m kind of curious as to why you didn’t try anything with me. Is it because you think you’re too good for me, huh? Mr. Big shot LA guy? Well, whatever. I’m not a tramp and don’t sleep around but you missed a shot at an awesome hookup last night.’
About half an hour later while I’m still in the meeting, she called and left another voicemail, this time crying,
‘I’m sorry about what I said earlier. I’m just having trouble adjusting to a new place. I’m homesick. You seem really great. Please call me back and please don’t ignore me. Please. I’m sorry.’
Needless to say, I didn’t call her back. Her friend, the receptionist, apologized profusely the next time I saw her. We didn’t talk much about it after that.”
Eight Drinks
“I online date quite a bit as I don’t have the time or desire to go to a pub to meet women. It’s also a great tool for weeding out the crazies. I met a girl on one of the sites and we hit it off via email pretty well. There were a few small ‘warning signs’ but at the time they seemed like general inquisitiveness. Signs like ‘What is your job?’ and ‘Does that pay well?’ She also had a constant drive for acceptance, compliments, status, and her devout materialism.
Being less cynical than I am now, we set up a date and agreed on a moderately fancy place in downtown Seattle. We set our date for seven pm and I made the reservation. When I arrived five minutes early, she was already at the table and had three empty drink glasses before her, and was nursing her fourth. I could tell her photos online weren’t up to date but they still represented her well enough. She dressed to impress but in my mind’s eye, I recalled something not being right about it all.
Throughout the date, she kept trying to impress me with things she owned, places she had been, and by name-dropping famous people she claimed to have known. Her continued emphasis on equating her worth to material things and her continued inquires about my worth such as ‘Do you rent or do you own?’ were rapidly rising from a warning to alarming.
When it came time to order, she chose the most expensive thing on the menu, surf and turf with lobster, and ordered not one, but two more drinks. She plowed through both drinks during dinner while only touching one or two bites of her entire meal. I kept my chit-chat small, enjoyed my meal, and let her continue her self-aggrandizement.
For dessert, she ordered a 50-dollar chocolate truffle mouse and two more drinks while I had coffee. I was beginning to grow concerned not just for my wallet but how she might actually be a hardcore drinker.
She had two bites of her dessert throughout the hour we talked and sent it off, like her meal, not requesting a box. As she siphoned off the last two drinks bringing her to eight drinks total in two and a half hours, I realized there was something absolutely wrong with her at a fundamental level, and getting any more involved with her would probably be a very very bad idea.
When the waiter appeared after the dessert, I asked him for the checks with an emphasis on the ‘S.’ On queue, she excused herself to the ladies’ room. The waiter got my subtlety and promptly returned with two bill books, placed one on her setting, and I gave him my card. She remained in the bathroom until the waiter returned with my card and the receipt.
As she came to the table complaining loudly about the bathroom, I bid her good evening and told her I really wasn’t interested in pursuing a relationship with her, but that I wished her the best of luck, and turned to walk to the door. About the time I got to the door, I heard her scream,
‘FOUR HUNDRED DOLLARS! I AM NOT PAYING THIS!’ and I walked out.
I never heard from her again but I hope she got the help she needs.”
“I Love Glasses”
“I talked to this guy online for a couple of days when we realized we had the same favorite bar so he invited me out for a drink. He was late and I started to get annoyed until he showed up and I learned his photos did not do him justice. He was so incredibly hot. I immediately felt like an ugly little troll, an ugly troll that just wanted to take his pants off. He bought me a drink and we started talking, both of us had admitted to being shy but we had a great conversation anyway.
After a few drinks, he offered to walk me home, so I knew where it was going and I was okay with it. I brought him to my room and he sat on my bed. I sat next to him and it was awkward and quiet. He noticed my glasses on the nightstand and put them on my face. He stared at me for a second, then climbed on top of me and kissed me. It was really weird kissing, then he said,
‘Do you think it’s weird I wouldn’t touch you until you had your glasses on? I love glasses.’
He then kept making really fake seductive faces while we got undressed, and right when I decided it was too weird and I should make him leave, he finished prematurely. He freaked out and I told him it was okay and we got dressed. He got under the covers and got really quiet and serious. I didn’t know what to do, I didn’t want him there. He started telling me how much he hated his life and that he was just using me.
I tried to talk to him so he’d feel better and hopefully leave, but he kept saying things that upset me. Finally, I told him to go and walked him to the door. He kissed me on the forehead and walked backward down my hallway staring at me until he got to the stairs.”
Wrong Number
“I created a dating profile and some random girl messaged me. She was pretty, pretty strange, and pretty open about being pretty strange. Most people on their first few dates show the best side of themselves. Not her. The fun stories she told included gems such as how she lost her v-card at 15 to a hobo who would hop trains in her town, and how said hobo was smuggled into her basement to live there off and on until her father finally found out.
Apparently, her dad wasn’t around much or didn’t use the basement. The other stories were also weird. I didn’t really feel like what she was sharing was any of my business, but I didn’t want to be impolite. At the end of the date, she wanted to hook up but I needed her to know we couldn’t be exclusive. The conversation ran itself: I’d never suggested we sleep together, asked to be exclusive, or indicated I was interested in hooking up with her to begin with. She just wasn’t my type and I wanted to end it with a hug.
When I said something like, ‘Hey, it was great to get to know you, but I don’t want to sleep with you,’ she started talking about how that was okay, but she was only doing other things if I reciprocated. Getting her to understand, in gentle terms, I wasn’t interested in anything with her besides a hug took a good ten minutes. I said we weren’t a good match, wished her the best in the dating world, and moved on.
Next week I had a 10-hour hike I had to take for my field biology class I’d put off until the last weekend of the semester. I called my lab partner after and said,
‘Hey, what’s up? Sorry I didn’t call sooner, I was on this ridiculous hike!’
I talked for about five minutes about the details of what I’d seen but our connection wasn’t very good. At some point, she asked,
‘Uh, what do you want?’
‘Duh, to talk with you, why else would I be calling?’ I said.
The conversation went on for about ten minutes before I realized I’d dialed the wrong Amanda. I was talking with last week’s date rather than my lab buddy. It was so awkward I can’t really put it into words. When I finally realized what I’d done, I asked her a few questions, played it off, wished her the best again, and hung up.”
Shrek And The Navy Boy
“I went on a date with a Navy boy who seemed smart and sweet online. He picked me up in this incredibly ostentatious yellow Camaro, which I had the sneaking suspicion he borrowed as it was a stick, and he was having a helluva time driving it. We decided to go walk on the boardwalk for a while so he pulled into a parking garage. In his attempt to park the car, he completely sideswipes the car next to us leaving yellow paint all across their car. He didn’t even act like anything happened, so I said,
‘Umm, I think you may have hit the car next to us.’
He got out, looked at it, then climbed back in and said, ‘I guess we should park somewhere else,’ and peeled out before I could even say anything.
Fast forward, the date was going poorly and it was miserably hot out so we decided to see a movie. It happened to be Shrek The Final Chapter, a kid’s movie. He had his feet on the seats in front of us which was no big deal until a dad holding his toddler daughter came in and the only seats still open were the ones in front of us. The dad went to sit down and the Navy boy didn’t move his feet. In fact, he moved his feet forward a bit so he hit the dad in the head. The dad looked back at us so the Navy boy sighed heavily, took his feet down, looked at me, and said,
‘My feet were there first.’
After the movie, he asked if I wanted to go to dinner, I said no so he dropped me off and asked when he could see me again as he had a great time.
We’ve been married five years now!
Just kidding, I took mental note of his license plates and called the parking garage. I did not see him again.”
Hissy Fit
“I had been talking to this guy from an online dating site. He seemed pretty lovely and kind of cute despite being a massive hipster with clear, giant glasses and all. He lived about two hours from me and decided to take a trip to meet me. I wasn’t opposed to it.
When he got to my place, he looked nothing like his photos. He was 5’3″ when his profile said 5’7″. He also had super crooked teeth and was just rather unattractive. Either way, I was still willing to give him a chance. I’m not that shallow. He brought a bottle of Reisling but I don’t really drink much. We went out to lunch which was nice enough and then went to hang out at my apartment.
I had maybe half a glass of Reisling while he finished the entire rest of the bottle even though it was well before four pm. The next thing I knew, he was begging me to make out with him. I gave it a go for a minute before becoming really turned off and stopping. I just wasn’t feeling it.
He then started complaining about how he was tired and inebriated and wanted to sleep. I told him that he was welcome to crash on my couch for the evening. He asked if he could sleep in my bed and I said that would be okay and I’d sleep on the couch. I guess he just really wanted to sleep with me because he started yelling and throwing a total hissy fit. He stormed out of my apartment to drive back to where he came from even though he wasn’t sober. Apparently, he got home safe. I never talked to him again.”
Moment Of Clarity
“At the time this happened, I was 26 and living with my parents. My father had lost his job, my mother broke her leg, and my grandmother was fighting cancer, so the whole family came together to help each other out. I moved home from the town I was taking college classes, took a full-time job in a pharmacy, and turned into a workhorse with 60-hour weeks. I had just gotten out of a bad relationship and was extremely lonely and cooped up in my parent’s house around all the depressing stuff. After a few months of this, I decided to get online and see if I could find someone to have a little happiness with.
I met a girl who looked gorgeous in all her pictures. We sent some messages back and forth and I found her to be pretty interesting. We agreed to meet so I got cleaned up, picked up some drinks, and headed to her place. It ended up being a three-hour trip because I didn’t realize how far away she lived. I was sketched out when I pulled up to her place because two teenage kids were hitting a cat with a jump rope in the parking lot. Somewhere in the distance, I heard god and my ex-girlfriend laughing together.
She came outside to greet me. She looked a bit different from her photos but she had a nice face and I had come a long way. I remembered our playful, interesting talks and gave her my best smile because I had already invested so much time and energy into being there.
We had a few drinks and watched a show on her couch while talking a bit. I learned she was jobless, did not graduate high school, and lived on government assistance. The worst part for me was she had no desire or plan to do anything. She was happy. I broke out the Jose Cuervo and we started taking pulls on the bottle. The sun was going down but not quickly enough. I was sinking faster than it was. We went out on her balcony and the Jose Cuervo came with.
Eventually, I started to kiss her. After a few minutes of kissing she went in to put some music on. Not but a moment passed before I heard the dulcet tones of ICP (Insane Clown Posse) drifting in the wind and I considered leaping from the balcony.
It turned out the girl didn’t have a bed. As she drank more, she began to share more about herself, and I’ll spare the details, but was apparent she was a very damaged person. My head was spinning from drinking, but I had a sudden moment of clarity. This girl was inebriated. Although she was of legal age to fool around, she was mentally not older than a high schooler and I knew I was never going to call her or see her after. I thought about what that might do to a damaged girl with issues.
I excused myself to use her bathroom and started drinking water from the tap to sober up. I remembered staring at myself in the mirror and thinking of how thankful I was for everything I had in my life. When I came out, she was passed out on her couch. I gathered my shoes, wallet, and keys. Money was missing from my wallet, but not much, and the girl didn’t even have a bed. I just shook my head and left.”
