1.
“I met a guy at work with whom I became friends. He asked me to his house in the country to grill some steaks and hang out. When we got to the house, it became a bad dream. While grilling the steaks, he peed out of his back door. I got busy baking the potatoes, and upon opening the oven, I discovered moldy food. Then, his ex-wife showed up wanting child support. Wait…it gets worse. The steaks came off the grill rare — very rare. I like mine medium-well. He did throw my steak back on the grill but proceeded to eat without me. After dinner, we would drink a beer and watch a movie. He excused himself and came back carrying what I thought was some kind of smoking device. It looked like a bong at first. To my surprise, he proceeded to tell me it was a penis pump. I left skid marks in his driveway!”
—Anonymous
2.
“I met a guy online, but we had a mutual friend who vouched for him, so I agreed to a date. He was rude and arrogant and said batshit things. I think the final straw was when he came back from the bathroom, put his wet hands on my face, and said it was pee. I left. The next day, he messaged me demanding I pay my half of the bill, even though I left before anything arrived. I sent his friend the money to transfer to him. I wanted nothing to do with the guy. I ran into him a few years later, and he was like, ‘Are you still mad?’ I said no, and he said, ‘Okay, cool. I know one of your friends and she’s smoking hot. Can you hook us up?’ Yeah, no.”
—Anonymous
3.
“While we were driving home from our first date, he said he felt bad about cheating. I told him I didn’t know he was married. He said no, he felt bad about cheating on his mistress.”
—Anonymous
4.
“I once had a huge crush on a man who often came to work with us from another agency. We talked, but I didn’t flirt because it seemed awkward. After a few months, he asked me on a dinner date. We went to a really nice restaurant near his home. It didn’t make sense for him to drive out to pick me up and then double back to the restaurant, so I offered to meet him there. As it was a nice place, I wore a dress, put on a little makeup, and did my hair. When I arrived, he was waiting, and we were seated. While waiting for the server, he said, ‘You look pretty tonight. I haven’t seen you wear makeup before. You wear it well. I thanked him. Then, he said, ‘In my experience, the only women who wear makeup well are models and whores. You aren’t pretty enough to be a model.'”
“There was a moment of stunned silence while I processed, and then I responded, ‘Thank you for the interesting evening.’ I got up from the table, pushed in my chair, and left. Thankfully, we hadn’t ordered yet, and I had driven myself. Maybe not the strangest date, but certainly in my top five.”
—Anonymous
5.
“When I was in my very early 20s, I went on a date with this Marine who turned out to be sooo immature. First, we went out to eat, and right after we sat down, he shot his straw wrapper right in my eye. He laughed but apologized. I didn’t think too much about it because it was an accident. Then, we went to see Saw II in theaters. I am not a horror movie fan, but he really wanted to see it. He laughed maniacally and was incredibly creepy during the most grotesque parts of the movie. It was both bizarre and embarrassing. Then, after we left the theater, he begged me to walk on the pier with him. I finally agreed, and as we were walking towards the pier, I saw two other Marines walking towards us, and I realized they were giving each other a thumbs up.”
“Turns out he had two of his friends wait on the pier for us so they could give me a thumbs up or thumbs down. I said I needed to head home, and he tried to kiss me. I said no, and got in my car and left. He called me within 20 seconds of driving away, asking if I could give him and his friends a ride to a nearby bar. I didn’t answer, so he left that message on my voicemail. He called me four more times in 15 minutes, so I finally answered and told him never to contact me again, and luckily, he listened.”
—Anonymous
6.
“I met a guy on Match who, in his emails and phone calls, was very fun. We agreed to meet up for dinner. When I got to the restaurant, he was drinking a beer at the bar. We got a table, and he added the bar tab to our dinner. Halfway through the meal, he said he had forgotten his wallet at home. WHAT?? I paid for the meal, even though I should have gone to the bathroom and left the restaurant. We walked out to the parking lot, and he asked me which car was mine. At that time, I drove a Dodge Nitro. I loved it. He said it was the ugliest car he had ever seen. So, I asked him what he drove, and he pointed to a rusty, bench-seat pickup truck. That’s fine, but why insult my car? The next day, he texted me to ask if I wanted to meet for coffee. I asked him who was paying. I never saw or talked to him again.”
—Anonymous
7.
“After a mediocre and short first date, he went in for a hug and promptly reached down the back of my pants and asked me, ‘Are you wearing granny panties?'”
—Anonymous
8.
“I was on a first date making chit-chat and having drinks. We went for a walk, and I tried to hold his hand. He FREAKED out because it was the hand his watch was on, and I could’ve accidentally scratched it. Nope. Big nope. I finished the date, said goodbye, and never talked to him again.”
—Anonymous
9.
“A man, who’d been a casual friend for years, asked me out. I declined, as he didn’t interest me that way. Well, he got all huffy and said that at my age (40), I stood a better chance of being ‘hijacked by a terrorist’ than getting married. What? I lost it. Through laughter, I choked out, ‘Well, I guess I’ll just have to hold out for that terrorist, now won’t I?’ There never was a date. We don’t speak. I’m now married.”
—Anonymous
10.
“This guy took me to golf and lunch at the pub beside the golf driving range. At lunch, he ordered one basket of spicy chicken strips (he didn’t ask me what I wanted) and two beers. He talked about his mom the whole time, ate the chicken strips without sharing them, then picked up my napkin and blew his nose into it at the table. Then, he looked at me and said, ‘You’re an acceptable date. Want to go on another one?’ I burst out laughing and said, ‘No, this one was enough. Thank you.'”
—Anonymous
11.
“I’d been through a contentious divorce trying to keep the property I had purchased before getting married. My ex was determined I would have to sell it, but we eventually reached a settlement in which I had to re-mortgage and pay him half the property’s value. I was working three jobs to pay that mortgage off when I got set up on a blind date with a guy who came highly recommended by friends. We went out a couple of times, and I found him unattractive and a braggart. He loved to put on airs about having money and connections, which raised some red flags for me. My friends kept asking me to give him a chance because he was ‘a really nice guy,’ so I kept things very casual and only saw him at group social events. He dropped by my place one day, stood beside me surveying the property from the lawn, placed his arm around my waist, and said, ‘Just think: Someday this could all be mine.'”
“My instincts were correct. After I rejected him, he found another divorcée who had her own place and moved in within weeks. I researched and found he was a complete fraud regarding his job, education, and financial status. Bullet dodged.”
—Anonymous
12.
“When I was living in LA, I met a rather attractive gentleman at a bar on NYE. I had just recently relocated, so I was super excited about it. We went on a few dates, and by the third date, he invited me to dinner with a couple of friends. Thinking it was going super well, I went out and purchased a new outfit and got all dolled up. While getting ready, I received a text message saying he didn’t want me to go to dinner because I’d simply have nothing to talk about and couldn’t possibly keep up with the conversation. You see, he had an EMBA from Wharton, and these would be other graduate friends. Basically, because I wasn’t as educated as him, I wouldn’t fit in. Such a pompous jerk. It’s gratifying to know I’m more successful than he is eight years on.”
—Anonymous
13.
“I went on a date with someone who had two beers and was judgmental towards me for not drinking on the date. I explained it was a personal boundary of mine. As we took a walk, he insisted on holding hands. Later, he slapped my ass. I immediately told him that wasn’t okay at all, and he ‘didn’t see anything wrong with it.’ WOW!! I had to ask: ‘What the hell makes you think that is even remotely okay or acceptable?’ He didn’t have a good answer. The date ended very shortly after, and there was no second date. Bullet dodged!”
—Anonymous
14.
“I had a guy I was chatting with who somehow tracked me down in a bar I hadn’t told him I would be at. I decided to be nice, as the bartender and bouncers were my friends, and I knew they were watching. It was an outside bar and summertime in Florida. He asked me why I wasn’t showing more of my body (specifically my stomach). I told him a few years back, I had emergency lifesaving surgery, which resulted in some huge scars. He said, ‘Oh, I don’t like scars. Can you get rid of them?’ I said, ‘Too bad! And no, they are a part of who I am.’ Not even five minutes later, he started trying to feel me up and then asked if I wanted to have sex in his car! I promptly said no, got up, and walked away.”
“He attempted to follow and grabbed my shoulder. The bartender and bouncer got to him before I turned around, and he was promptly and painfully escorted to his car. They also escorted me to my car later that night, checked my car for air tags, and then followed me home. I’m thankful for friends!”
—Anonymous
15.
“We were having a great conversation and started getting vulnerable and discussing our past traumas. I told him about a sexual assault. Shortly after that, he went to the washroom…and sent me a dick pic!! When he came back, I had no words. He asked if I liked what I saw, and I just stared at him. I said, ‘I just told you about an assault, and your response was to show me your penis?!’ He said, ‘Oh, you’re one of THOSE girls who always has to play the victim.’ I told him this was a great opportunity to see we had different communication styles, and I suggested this whole thing should end now. He pulled the ‘Well, you’re a fat, ugly bitch, and I didn’t want to date you anyway!’ card. Cool story, bro.”
—Anonymous
16.
“We met at a happy hour. He was very self-involved and already seemed a little tipsy. At the end of our ‘date,’ he asked for separate checks. I had one drink. It was $1.00. True story.”
—Anonymous
17.
“Blind date set up by my best friend. Over lunch, he told me I shouldn’t have bangs because they cover my face, and I’d be so much more attractive if I’d replace my glasses with contacts. I laughed so hard that I couldn’t eat. He was clueless. I told my friend, ‘Thanks, but no thanks,’ when she asked how it went.”
—Anonymous
18.
“I went on a date with a guy I met online during COVID when you had to show proof of vaccine. We met in the parking lot of a restaurant, and he asked if we could hang out in his car for a few minutes. It was filled with trash, and I felt weird, so I invited him to mine. We talked briefly, but he would stall whenever I asked if he was ready to go inside. After about an hour of egotistical, ‘I know better than everyone’ kind of conversation, he confessed he didn’t have proof of vaccine and didn’t even bring his wallet. He hoped I could order takeout and get it for him instead. I asked him to get out of my car, and I drove away.”
—Anonymous
19.
“I went on a date with a guy who claimed to be an actor. I found him on IMDB with one credit for a quick cameo in Trailer Park Boys. He didn’t even have any lines, just a glance. I guess that was enough for him to take on the title. Anyway, he spent the entire date telling me all the ‘insider secrets’ of the movie industry. I played along; the conversation was kind of fun. Then he kissed me and broke down crying. He said I kissed like his ex and then spent the next two hours crying over her and asking me for advice on how to get her back. Not my worst date (which is kind of sad), but I definitely didn’t sign up to be his therapist either.”
—Anonymous
20.
“I dated someone around Christmas time. I helped him win a prize for the best decorated door. Anyway, he once asked, ‘Would you change anything about me?’ I said no, and he proceeded to tell me everything I needed to change about myself. I laughed and never spoke to him again.”
—Anonymous
21.
“I was at a church ice cream social for singles. I’m a non-working widow. One of the guys approached me and asked, ‘Where do you get your money?’ I was so shocked that my only comment was, ‘At the bank, like everyone else.’ As I walked away, I heard several guys yelling at him. How rude!!”
—Anonymous
22.
“On a first date, I met a guy at a nice bar that was nearly empty. We sat at the bar and ordered drinks. He asked if I liked oysters. I said no, and he replied, ‘Offering you oysters is like throwing pearls to a swine.’ I fought the urge to punch him in his face and left. Lasted all of 10 minutes. WTH?”
—Anonymous
23.
“We matched online and met in the middle. He arrived half an hour late and ordered food he knew I was allergic to. He told me I was wrong in identifying the song the live band was singing because he had ‘perfect pitch,’ and I clearly didn’t. At that point, I went to the washroom to regroup. When I returned, I told him I just didn’t see a future between us. He told me I was delusional. I paid my portion of the bill and walked out, blocking him on everything.”
—Anonymous
24.
And: “I went on a date with a guy to a restaurant, and after about an hour of superficial chat, he got up and asked me to have sex. I told him that I had no intention of having sex with him as of yet. He reacted angrily and said: ‘So I just lost the food I bought for you!’ The guy was a professional, educated person, but a troglodyte regarding women.”
—Anonymous
UGHHHH, I could just scream. Dating sucks. Women, if you have a story you’d like to add to the mix, feel free to submit to this anonymous form.
Note: Submissions have been edited for length and/or clarity.
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