January 28, 2023 | Maria Cruz

People Share Their Biggest Online Dating Failures


Online dating can be a good way to meet someone new and spark a potential relationship. However, you never really know the person you’re chatting with until you meet them online. And sometimes, it doesn’t even take a face-to-face meeting before they change into someone else entirely. 

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#1 Lucked Out

I matched with someone on a dating website. We got to talking and he seemed like a chill dude, even though there were red flags (he insisted we were dating before we met and I wasn't allowed to talk to anyone). I agreed to meet up with him at a cafe by work. I organized with my receptionist for her to call me at an allotted time and tell me I had to come back to work, so I had an out. 

I met with the guy for coffee and it seemed good enough. Then my girl rang me, so I told him I had to get back. His response was, "I've got my work van here, do you want to jump in the back and have a quickie?" I noped out of there and went back to work. A couple of months later, he ended up coming into my work to see my boss. I made polite small talk with him. When he left, my boss called me into her office to ask how I knew him. Turned out, he was married to my boss’s niece.

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#2 Pregame Bud

I met with a girl at a pub in Philadelphia on a Friday night. It was fun and we partied, but I noticed that she was pacing much faster than me. I had around four in the time it took her to down seven glasses at $15 a pop. We were getting along well and she said that she needed to use the restroom. She took her jacket and purse to the restroom. I didn't think much of it but after an hour of sitting alone, I realized that I got used for a heavy pregame. The bartender kind of realized it. When I asked for the tab, he shrugged and said, "Bad things happen, mate. I took two drinks off your tab."

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#3 Only Offer

The first time I contacted someone (it was via The Onion personals, which were really a thing in 2005), I just made fun of a band she said she liked. I wrote something like, “My only problem is that you are into (band).” She replied (as she should have), “My only problem is that the only thing you offer is criticism.” I still cringe.

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#4 Send Pics

I was talking to this one girl who mentioned that she was into photography. Trying to show an interest, I asked her to send me some pictures. However, she thought I was asking for explicit photos, so she deleted me. I realize that I worded the question poorly, but when I went to explain myself, I found that she also blocked me. 

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#5 Just for Fun

My biggest fail was waiting too long to start. I spent nine years trying to find a girl while going to parties and the club. Turns out, I'm fairly bad at that, which probably wasn't all that good for my self-esteem either. A female friend then thought it would be fun to create an online dating profile and swipe for me during a party. 

I spent the next few days being mind-blown at getting matches. I sucked at texting but progressively got better at it. After a few months of going on a ton of dates and getting better at that as well, I finally found my current girlfriend. I developed more at flirting and understanding dating in those six months than from birth up until that point.

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#6 Not Today, Bot

I matched with a girl who looked really cool. For my first message, I complimented her hair. She responded with something along the lines of, "I'm so glad you messaged me, most of these guys just match and never message." I've seen almost exactly the same line before from bots, so I assumed she was a bot and said something snarky about it. She replied, upset, and then unmatched me.

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#7 Fewer is Better

Putting all my eggs in one basket. Once I start a conversation with one person, I just stick with that person until I know it's not going to go anywhere. I can't deal with trying to remember stuff about two+ people at the same time. I don't mind, though, if the person I'm talking to is talking to more than one person. So long as if we're on a date, they're not on the phone with them or mix us up.

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#8 Multiple Messages

I chatted briefly with one woman before telling her I was going out with friends. The next day, I checked my messages and she had sent some. It started with, "Why don't you come around to my house and get partied out with me?" It then progressed to, "Why are you ignoring me?" It then went to, "I think you're gorgeous and we will be good together.” Finally, it got to, "Don't you ignore me." I sent her a message the next day to never contact me again.

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#9 Social Cues

Voice inflection and social cues are what so many people can’t seem to grasp when I explain to them that I don’t do online dating. If they’ve never experienced what it’s like to have this happen, they just can’t understand it no matter how much I try to explain it. And to me, it’s a huge part of my attraction (or lack of) to a person.

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#10 Why Am I Doing This?

I met with this very attractive woman off an upper-middle-class online dating site. She was way hotter than me. At some point during the evening, she leaned forward on her stool, narrowed her eyes and said, "I know there was some reason I swiped right on you." Because at that point she couldn’t remember.

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#11 Pulling Pictures

I once had the misfortune of going on a date with a girl who told me that she found children very attractive. After that, I stopped mentioning that I had a child on my profile (and took down the picture of me and my daughter). I just brought it up with the girls that I felt were likely to stick around after meeting in person.

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#12 Do Your Research

I dated a guy who was in a Poli-sci Ph.D. program (confirmed) and had a law degree (confirmed) but had “left practice because he didn’t enjoy it.” Nope, that wasn’t the reason why. I looked it up and he had been arrested for a federal hate crime as part of a far-right movement. He was, therefore, ineligible to practice. Thank God for Google.

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#13 You Pick a Place

I once found a wonderful guy and then canceled the date last minute because I wasn't over my ex yet. The joke was on me, though. We rematched 10 months later, he gave me trouble about my behaviour last time and told me that because of that, I had to come up with an idea. March will mark our one-year anniversary.

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#14 Scary or Something

I had about given up on dating in general after I broke up with another loser I had met on there. But I decided to revamp my profile a little and put exactly what I was looking for. I included that I’m a professional with my own place, car, a full-time job, and a college degree. I also added that though education isn't a deal-breaker, I just want someone I can have a conversation with. It was pretty straightforward. I included that I like fun stuff too because I’m not a very serious person. I went from getting several messages a day from guys to maybe a message a week.

Since I'm a weirdo, I made a second profile. I had zero pictures of my face and only partial body pictures uploaded. I had pictures of me with boxes on my head, wearing weird masks, all kinds of things. I put how I only read the Necronomicon, I have antlers, and I glow in the dark. I got a ton of messages to that profile. 

One of them ended up being my current partner of six years. Once I sent him an actual picture of me, he said he recognized me from my other profile. I asked later why he didn't message me on that one and he said I seemed scary or something. Now I know that asking for a guy with goals is scarier than potentially being an antlered necromancer.

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#15 Too Tall

For the last five years, my biggest fail was when people would look at my profile and see that I’m Asian. They then don’t read the very first thing that I wrote, which is that I’m 5’10”. Then, they would be shocked when I show up at or above eye level. One person had the gall to tell me he, “had a great time, but I really thought you were more, you know, petite" while gesturing at my figure and then compacting it.

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#16 One-Way Street

The biggest fail was my ex. We spent five and a half years together and I was super supportive of her. I got her on her feet, covered expenses for the first two years until she stabilized, helped her find her first job, helped her through college, and helped her with her first job after college. But then the moment I started struggling with money (we moved across the country for the one she got), she kicked me out. I mean, I was struggling for about a year. A month after she kicked me out, I managed to land a job. Good times.

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#17 Swiping Too Fast

I was swiping through these online profiles so fast that I accidentally swiped left on a girl I wanted to match with. So, I used a subreddit to get her information and messaged her on Facebook. I thought she would appreciate the added effort, but she ended up thinking I was a creep instead and then blocked me.

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#18 Wait, They’re Interested

I used the free version of an online dating website to browse, then decided to sign up. I very quickly realized that it didn’t have anything to offer me, so I cancelled my subscription and got a refund. Suddenly, I then had 20 different emails about different women interested in me. It was way too coincidental.

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#19 Neglected Wife

Her husband was easily the biggest obstacle I’ve come across when online dating. You have no idea how many neglected wives are out there online and they love to omit the fact that they actually have husbands. Watch out for the attractive, older women. They’ll break your heart and her husband will break your neck.

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#20 Rinse and Repeat

When you make a profile and get zero matches. So, you give up and delete it. Then, you wait about one or two years before making another profile. Then you get no matches. So, you give up and delete it. Now that 100% of the platforms lock you out of messaging unless you've been matched first, online dating is pretty much gone to me.

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#21 Girl Friends

I usually end up befriending the women I meet instead of actually dating them. To me, a girlfriend should be a friend as well, but that doesn't work for most people. So, I just have a lot of friends now. I mean, it’s all cool until you end up developing a crush on one of them who doesn't feel the same way about you.

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#22 That Fast

I tried a dating site for a while. After a month or so, I contacted and talked with this girl. Things seemed to be going well. We had similar interests in music and movies, a similar sense of humor, etc. Eventually, we were talking about hobbies and I casually mentioned I played Magic the Gathering. She immediately unliked me. Like, she had time to receive the message, click the menu and hit unlike. It was that fast.

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#23 A Girl’s Gotta Eat

When I started on a dating site, getting used for your money was super common. I came across it a good handful of times before adding to my profile that we would be going Dutch for the first few dates. After that, my results improved in quality, even though they reduced in quantity. The really irritating part was when I came across two separate girls who just openly said they were only there for a free meal and I wasn't the type they'd ever go for. Like, wow. The stones you have to have to do that are far more massive than mine, therefore it's a no from me.

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#24 Testing the Waters

Online dating is just a way to meet more people to test out in person attraction. The most common mistake, to my view, is people getting too attached before they meet in person. Message a little to see if there's personality potential, meet quickly to see if there's actual potential. Wanting to know people in person isn't the barrier you think it is, the whole point is to meet up eventually anyway.

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#25 An Hour Late

I actually met a smart, tall blond girl on Facebook. I was super smooth and got her to go on a date with me. She was an hour late to our date, but she eventually showed up. Unfortunately, during that hour, I partied way too hard and lost consciousness. So, not only did nothing come of that, but I also lost the friend whose comment I met her on.

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#26 Uber Ride

I went on a date with a chick one time and her profile gave off no red flags. The way she messaged and texted also gave off no red flags. I got to the place and she looked a little different, but I let it slide. She began to tell me she forgot to take her bipolar medication, so she shouldn’t order too much. Then proceeded to have five Long Islands by the end of the night.

She told me she wanted to come back to my place. So, we went back and watched a little TV before her phone rang. She silenced it and I didn’t think too much of it. Then it rang again… and again. I finally asked and she said, “That’s my old man, he couldn’t hold me down.” I told her, “Okay, well I'm not one to get between people” and I offered to buy her an Uber home. 

She whined for a while but I was done with her and this date. The Uber eventually pulled up and I walked her outside. What a coincidence, there was “her old man.” The guy came at me, trying to get in my face. She started yelling at him, calling him a psycho for tracking her phone. They started arguing pretty bad and I slowly started backing away. 

Within five minutes, they were making out in the back of the Uber, which I got charged $15 for for making him wait. They didn’t even wind up using it to get home. The “old man” eventually told the Uber driver to just go because he was going to drive her home. And that was that pretty much. I went back inside and watched Rick and Morty with my cat.

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#27 Something to Talk About

I met someone through an online dating site once. We hit it off really well for a while and would actually chat with each other for a good year on the phone. Once we met each other in person, though, we seemingly had absolutely nothing to talk about. Honestly, it was probably the most awkward encounter of my life.

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#28 Orlando Bloom

I only met up with one from all the matches from all of the ones I had. He looked like Orlando Bloom. I got so nervous, although he was very nice to me. Turned out, he just wanted to take me to bed, so I left. At that time, I hadn’t been with anyone yet and was scared of losing it to someone who didn’t care about me.

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#29 Hi, Hi, Hi

A girl sent a one-word message, "Hi." Okay, it's not easy starting a conversation, so no problem. I replied with a medium-length message. I commented on some interesting hobby mentioned in her profile and asked for more details. I told her about my day and some other random stuff. Overall, a good effort. The next day, she replied with, "Hi, how are you?" She was pretty.

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#30 Three Days Later

I once told a guy (via text) that I had to go because my lunch break was over. When my shift ended, there were tons of angry messages from him asking where I was and why I left so suddenly. I told him it was because my break was over and I can't text when I am at work. He then started apologizing to me and told me he was afraid he had lost me and that I hated him. We had "known" each other for three days and never met in real life.

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#31 Self Proclamation 

A few months ago, I went on a date with a self-proclaimed communist. He said this loudly, in a Chinese restaurant. When asked what kind of communist philosophy he was drawn by, he replied, “Oh you know, normal communism. Not North Korea communism.” All I could think of was how most communist countries were totalitarian regimes who starved their people and wondered if this is what he meant by normal. He proceeded to douse the stir fry we ordered with chili oil instead of partitioning off a serving for himself and seasoning that. It stood out to me as a particularly classless cherry on top of a heaping poop sundae.

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#32 Breaking it Off

My fourth date on a dating site went horrible. I thought this girl was perfect and we actually spent the whole day together. When I got home, we still talked and I thought it was a sure thing. Two days later, she stopped messaging me altogether and told me the day after that we need to break it off. Apparently, she recently started seeing someone else and felt bad just abandoning him like that. It broke my heart but we remained friends. I asked her out again a week later and she said yes. We’ve been together a year and a half now.

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#33 I Really Can’t Stay

I was on a dating site and matched with a really pretty woman (she was in her mid-late 30’s). We met for dinner a couple of times and went back to my house. After we were finished fooling around, she told me that she couldn’t stay all night due to her husband coming home from his job. (He was an overseas trader and basically worked in the middle of the night.) She couldn’t understand why I just didn’t want to have a casual relationship with her. 

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#34 What’s in the Box?

We met online and dated for several years. We had our issues, but we always worked them out. On Christmas morning, she was in a foul mood and told me to take the presents she bought me and to leave her house. She didn't even want to open the presents I got her — including an engagement ring. It still hurts me.

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#35 Creating the Bio

I always made my bio too long. I really took the time to type it up, even after realizing no one read them. I had more fun making the bio and answering the questions than using the site for what it was for. Also, I couldn't stand one-word answers and ended up writing paragraphs. I'm really bad at talking to people through text I guess.

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#36 Ditch Her

I talked with a guy a lot over text for a long time, getting pretty close. One time, I was shopping with a friend and we decided to go see the last Star Wars movie before heading back to her place to get ready for a party. I sent him a text, asking if he'd like to join us for the movie. I didn't realize he had to catch a train. So, he came in late, smelled terribly, kept trying to talk to me during the movie (I hate that), and tried to convince my friend to leave us for the night. But, I was supposed to sleep at her place and he didn't live in the city. 

I didn't want to be left alone with him because he gave me creepy vibes. After that, I told him I didn't want to keep in touch. He kept sending me texts even after months of no contact, saying I was the love of his life. He ended up insulting me and then apologizing by making a website with a letter on it. I blocked his number.

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#37 Close Enough

Please, please post recent photos of yourself. My one friend's online picture shows him 40 pounds lighter from a few years ago. My other friend’s photos show her from 11 years ago. She thinks she looks the same. She does not. Yet, they both wonder why they’re not having any success with the online dating thing.

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#38 Dodging a Trainwreck

I once matched a woman who was nothing short of great. She kept conversations going and wasn't afraid to talk about deep or dark things, her humor was so similar to mine, and she was absolutely gorgeous. I was a few months out of a breakup and thought I was doing okay enough to try dating again. I was not. Despite being over my ex, I wasn't overusing substances to cope with the rest of my life. I smoked the morning of the date to quell the anxiety about meeting someone new for the first time in a couple of years. The exact opposite of what I wanted had happened. The date went horribly and after talking for a few more days, she admitted she wasn't attracted to me anymore. I think about that from time to time, but I don't blame her for dodging a trainwreck.

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#39 Unanswered Questions

I matched a really cool girl online. We clicked in so many ways. We like so many of the same things and were always quippy with each other in a playful way. After a month of talking, I was smitten. We set up a date and met. I was amazed at how pretty she was. I mean, drop-dead gorgeous. She… was not so enamored with me.

Something felt off the entire date. She was not as interested in anything we were doing nor with our conversations. After the date, she sent me a message saying that she didn’t want to continue talking. I asked her why and she didn’t respond. I still don’t know how I messed up, but it pains me to this day. She was a great woman any man would want to have in his life.

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#40 Too Many Texts

I’d have to say that it’s when you send too many text messages and wind up scaring potential matches away. I now know how annoying it can be. Time zone differences don’t mean you have to send a million messages at a time. They could be working, or sleeping, or just out with friends. Just let them live their life.

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#41 Going to Canada

I talked to a girl who lived in a town 25 km away. She was nice and pretty so I asked if she wanted to meet up. She said yes, so we met up at her farm. She was a terrible conversationalist, though. I couldn’t get her to talk about anything and when I talked about myself, she seemed really bored. I was halfway through a sentence before she interrupted me to suggest going to a shop in town.

We went there, still having a terrible conversation. I then decided to talk about my trip to London and that actually got her interested. She talked for five minutes about how she always wanted to go to Canada as a little kid and that the next year she was finally going…  to get married. I honestly thought she was joking but later realized she was serious about it. 

The rest of the date went pretty poorly too. We didn’t watch a movie like we planned, we watched the rest of the movie she had started watching the night before. She took a bite of her burger and threw up in the toilet for 10 minutes because it was too greasy or something. She then suddenly remembered she had to go pick something up from a friend’s house 70 km away and I needed to leave immediately. So, I did. I obviously had no interest in dating her after that.

The next day, I decided to actually send her a text message and ask how she was doing. I thought I would check in because she mentioned going through some depression recently. I didn’t feel right just ignoring her after that. It’s been almost two years since that date with her and I'm still waiting on the reply.

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#42 Buy Me Taco Bell

One time, a girl online posted, "Buy me Taco Bell" on her about me. Being the guy that I am, I messaged her that I'd take a taco and slap it across her butt (for my own intrinsic giggles). Weeks later, I deleted my profile. Years later at some art show, there was a girl sharing a book she published about the disgusting things men have said to her via online dating. 

I opened the book and in fine print read the words "I'd take a taco and slap it across your butt." I looked the author in the eyes and told her men are disgusting. I also told her that whoever said that is a piece of trash. That night, right before I fell asleep, my brain connected the dots as to who that piece of trash was.

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#43 Facebook Friends

I saw a cute girl with some things we had in common. I sent her a few messages, we chatted a bit, things went well and we became Facebook friends. Her first post the next day was something like, “Well, can’t move back in with my parents, don’t want to be homeless, so guess me and the kids are moving back in with my hurtful ex!” 

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#44 First Impressions

I picked her up and got mauled by her dog while she and her roommate just watched. On the way to dinner, we were in my car and she said she was a strong anti-vaxxer. I should have just stopped the car or dropped her and said this wasn't going to work out. I could have saved myself the cost of an entire dinner.

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#45 Same Results

Spending over a thousand dollars on gold memberships and boosts in the belief it might help me meet someone. Over a year of trying and all that money, I’ve only managed to get a handful of matches and not a single first date. I took a break from it, but I’m giving it another try at the moment and have the same results so far.

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#46 Taking Out the Fun

I read through every profile that had a long bio and matched my interests. I have to say that, although it was cool to know so much right before the get-go, it takes a lot of the fun of experiencing the shared interests and opinions together. Also, as a victim of needing to write long paragraphs, some people, including me, are way better off just talking naturally instead of talking through text.

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#47 In Prague

I have so many online dating horror stories. I think one of the worst ones was meeting this guy who appeared to be nice. We were both interested in dating, so we kept seeing each other. But unfortunately, he worked as a teacher in Prague. So, every term he'd leave for work. When he got to Prague, he told me it was over as he met someone else. 

When he got back to England in December, he was insistent that he didn't meet someone else and he loved me and wanted me back. I'd met my current boyfriend then so I said no. A year later, he messaged me out of the blue telling me he was engaged. Turns out, he had a girlfriend in Prague who he's been with for four years and I was the girl he was with on the side. 

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#48 Part of It

My biggest fail is honestly just still using them. It's never a different outcome no matter how many times I download, delete, and re-download whatever site. There are tons of matches and conversations, I meet a few new people in person, but nothing ever sticks. I feel like everyone on there is just a serial dater who likes to think they want something real, but can't settle because if they just keep searching, they might find something even better. It's a viciously perpetual cycle, it's shallow, and I'll be the first to admit I'm part of it.

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#49 Major Blow

I once tried to sign up for a site. It was hard because I really felt like I was scraping the bottom of the barrel by resorting to online dating, but I was an abysmal failure in real life. I spent a half-hour filling out their questionnaire only to be told that they would not be able to match me with anyone and they basically denied me for membership. That was a major hit to my self-esteem.

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#50 Friend List

I was talking to this girl and after 48 hours of doing so, she went insane by sending me screenshots of my friends list. There are close to five thousand people on that account. She called me crying and accused me of sleeping with every single person on my list. She even took screenshots of someone's profile because it said she was a tattoo model. It was insane, but hilarious because she was acting like we had been together for years. We hadn't even met in person.

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