1. Submitted by kiah4c
I went for a drink with a guy I had been chatting with online. He seemed pretty normal (good job, intelligent, funny). His first question on sitting down with our drinks was whether I was up for anal. I bypassed and watched him drink his body weight in shots before he started crying about his ex-girlfriend and then threw up down my shoulder when I was trying to walk him home. This was around 18 months ago, and he still messages me from time to time with a "hey," or my favourite, "I miss you."
2. Submitted by naughtynurse99
Met a guy who seemed to be decent. We went to see a movie, and he kept talking about my feet — how "beautiful and sexy" he thought they were. I was like, "Thanks...?" Later, during the movie, he asked if he could suck on my toes. I said, "Definitely not." A few minutes later he dropped something on the floor, and while retrieving it tried to put the toes of my crossed legs in his mouth. I accidentally kicked him in the face. I was so shocked! I excused myself to go to the restroom and just walked straight out the door and left him in the theater.
3. Submitted by Danica Maxwell (Facebook)
I had an online dating app for exactly one day because the first person to message me sent me a long, detailed, emotional message asking for permission to masturbate onto my socks.
4. Submitted by Leyna Picariello (Facebook)
I met a guy on OkCupid, and we hit it off pretty well. After we hung out a few times, he came over to my place with a bottle of wine and a movie. He wasn't supposed to stay the night, but he lived 45 minutes away, it had snowed earlier, and I lived in a very rural area with a lot of hills and curves. So he decided he was going to stay that night instead of driving home. This only irritated me because he didn't really ask, he just decided. But the best part of the night was right before I went to bed (he was staying on the couch): He asked me if I should change my pad. I looked at him quizzically, and he said, "You need to change your pad before you go to bed — you could get TSS [toxic shock syndrome]." He proceeded to argue with me for a solid 10 minutes about whether or not I should change my pad. His argument was that he was an EMT and has a sister, so he "knows all about these things." My argument was that I've had a vagina for 20 years. Needless to say, he went home the next morning, and I've neither talked to or seen him since.
5. Submitted by alyssaloftus28
I once received a message from a man asking if I would give him a rim job, because I looked like the type of girl who does that.
6. Submitted by nkrjj95736
I went out with a guy from MeetMe. Things were going really well, and he eventually almost moved in with me and my family. Then I caught him looking down my 12-year-old daughter's shirt. I broke up with him and didn't blink twice. Recently found out he is awaiting a hearing for a sexual attack on a child under 12. I dodged a bullet and will never trust dating online again.
7. Submitted by Georgieroset
I met a guy on Plenty of Fish. We began messaging, and he seemed like a nice person, so we exchanged numbers. After a few days of talking on WhatsApp, our conversation fizzled out, and we stopped talking. A couple of weeks later, totally out of the blue, he sent me a picture of a random woman's boobs. Confused by this, I just sent back a question mark, and he then said, "Send more." I am not the kind of person to send pictures of myself to people, ever, so I politely declined his request. He then said, "Send me more or I'll send that picture of the boobs to everyone you know!" "Whatever, fuck off," I said, knowing he was bullshitting. He then started reeling off names of people I'm friends with on Facebook, even though I hadn't told him my last name and we weren't Facebook friends! I was incredibly freaked out and threatened to call the police, which scared him off. I blocked his number and set all my Facebook settings to private, and I've not been on POF or anything similar since.
8. Submitted by courtneyn3
This guy sent me this message on Tinder: "pizza and anal?" I sent back something about how I would definitely take the pizza but pass on the anal, and he replied with, "as long as i can suck your toes, we're golden." Barf.
9. Submitted by KattieQ
I was once talking to this guy online and after a few hours of nice, PG conversation, he did a complete 180. He asked where I worked because I looked familiar... He said I looked like a girl from an amateur porn video. I knew that was not possible. He then asked if he could jerk off while we continued our normal conversation. After he tricked me into continuing the conversion for a few more minutes, I told him good-bye. Then he barraged me with dozens of lengthy messages asking to help him orgasm by telling him what he was doing was normal. Apparently he had issues with disapproval and couldn't finish without me telling him the simple letters "OK." I never responded.
10. Submitted by katet4dbf41478
I had been chatting with a guy on Yahoo Singles for a while, and we got along fairly well. When he asked me out to dinner I figured, sure, why not? It was singularly the most awkward and uncomfortable evening I have ever spent on a date. We spent our time attempting to make disjointed conversation... At the end of the evening we just simply said good night, and I figured that was the end of it. Approximately six months later, I received a message from his Yahoo account that roughly said the following: "Hi! This is X's brother. This is going to sound really odd, but X is in prison for a few months (a big misunderstanding!) and I know he'd really like to hear from you. His address is through the ABC Correctional facility. Please write him!"
11. Submitted by estees2
I was speaking to this guy on Tinder, and after only a few minutes he asked me if I would marry him for $10,000. No joke. Apparently he was a foreigner and wanted to become an American citizen. He couldn't comprehend why I declined. He said, "Other people would do it for half the money!" I was like, "Not me, hun!"
12. Submitted by SamanthaG49
Met a guy online, and we hit it off on our first date. A couple weeks later we had gone on four dates, and he knew where I lived. That's when it started getting weird. He wouldn't return my phone calls, so after a week I stopped trying. Not long after, I glanced out the window of my house and saw him parked a couple houses down with another person in the car. I waited to see what he would do, and he drove off an hour later. A couple days later, he was back, except parked in a different location. I started to get freaked out. There was also a second person in the car that time. They left two hours later. The third time I saw his car outside, I was poised to call the cops. I didn't get a chance because there was a knock on the door. I opened it to a very pregnant girl on my front steps. She began to rant: How could I date a guy with a girlfriend, did I not have any morals, who did I think I was trying to steal her man, etc. I let her go on for a while before I interrupted her, told her I had no idea, and I asked why she was mad at me since I wasn't the one cheating on her. I found out that she forced him to drive to my house and sit outside nine different times. NINE. She wanted to see what I looked like and have him confront me and break it off, but he wouldn't go up to my door. I wish them all the best.
13. Submitted by angelag4752
My first experience with dating after my divorce, I met a guy who ended up being a sexual predator who "forgot" to put himself on the sex offender registry. He tried to get me to send him naked pics of my daughter, under the guise of being a nudist.
14. Submitted by cbarts887
I once received the following message on OkCupid:
"I came across your profile and was quite enamored by such an articulate, heavenly blessed beauty. I would be kicking myself if I didn't ask, so I was wondering if you would accept an engagement of witty banter between two intellectuals. Of course this "engagement" may start off as purely platonic, but my sensual desires will most likely guide our cohesive unity down more erotic, lascivious, and sexual paths that will include, but are not limited to, passionate make out sessions under the starlit sky, dry humping, fondling each other's naughty parts, and an abundance of new, uncharted sexual positions where I assert my pure dominance in establishing a realm of absolute sovereignty in your nether regions. Is this something you would be interested in pursuing?"
15. Submitted by Kris Woods (Facebook)
eHarmony matched me with my ex-husband...after we were divorced.