25 Wild Dating Red Flags That Made People Run The Other Way

First dates can be a mix of excitement, nerves, and unexpected surprises. While some turn into love stories, others take a nosedive straight into disaster. Reddit users recently shared their biggest “Nah, I’m out” moments from dates, and some of these experiences are downright shocking.

#1

Image source: CaffeinatedRob_8, pressfoto / freepik

Attempted to rekindle a relationship because we bumped into each other at a happy hour, and had a fun conversation—and thought perhaps things ended prematurely.

She was game for grabbing dinner, and even suggested a good Italian place that she had been wanting to try.

Done! Reservation booked. Time set.

The day of our date arrived. We were supposed to meet there separately but mid morning she texted asking if she could get picked up.

Sure! No problem.

She texted again. This time asking if we could change the reservation time to an hour later in the evening.

Ok, I’ll see what I can do. Done.

Another text. This time asking about possibly going to a different restaurant because one of her girlfriends suggested a “better” spot.

I actually reserved a table at said “better” spot at the later time and everything.

Oh. But then I found out that she didn’t want the later time at the “better” spot. She wanted to go back to the original time.

I forget exactly what my text message said at this point but it was something along the line of “I’m sorry to do this but I’m just not hungry anymore.”.

#2

Image source: ned23943, Drazen Zigic / freepik

When this first date of ours turned out to be an Amway recruitment meeting.

#3

Image source: fartsypooper, lookstudio / freepik

He kept telling me how much I reminded him of his daughter while he kept trying to grab my face to try to go for a kiss. When he went to the bathroom I ran out.

#4

Image source: jennsnotscary, freepik

He said he was a bartender. We went to his apartment, he said he’d make me a drink. Then he put my drink in a different style glass than his. I asked to add something to it, i took a single sip, noticed he was watching me very intensely, I told him “try this its so good!” He didnt swallow.

I left.

#5

Image source: AdFresh8123, zinkevych / freepik

It was a blind date. Surprise! Two of her friends “just happened” to show up. She invited them to join us without even asking me.

They pretty much ignored me and ordered the most expensive items on the menu, including drinks. Every time I tried to join in the conversation, I was rudely dismissed.

I realized pretty fast that I was being scammed. They barely paid attention when I finished my meal and excused myself to go to the restroom.

I went to the bar and had the bartender call my server over. I was a regular there, so they knew me. I told her what was up, and I wanted to pay my share of the check. I tipped her generously since I knew my “date” was probably going to screw her over.

I warned my server that they might try to run out on the bill when they figured out I wasn’t a sucker. I left and met some friends at a bar I knew they would be at. We had a good laugh about it.

A few days later, I stopped back in the restaurant for lunch. The bartender told me I was right. He said it took them a while to catch on that I’d left. They did try to dine and dash and got caught.

The manager threatened to call the cops. They ran up a huge tab because they had several drinks each as well. One of the girls had to have her dad come down and pay the bill.

#6

Image source: RelationshipIll9576, freepik

I’m a gay guy. Had a date with a guy that seemed okay until the end of the night when he told me he had just come out to his family – during his sister’s wedding that caused a bunch of drama.

No thanks. If you aren’t mature enough to realize that this is your sister’s special day and that you made it all about you, then this ain’t gonna work.

#7

Image source: Psychotic_Parakeet, freepik

I have two nightmare dating stories, but this one takes the cake.

About 17 years ago, I dated a guy that I met off of Match. We had a good connection via messaging, phone calls, and we went on four dates. After the fourth date, there was a sudden change. He would take days to answer back, so I figured he was just busy and I just left him alone. After a while, he finally contacted me to go out on a fifth date, and said let’s go to Venice Beach, as I have never been there before.

When I was in the car with him, he never said a single word. He drove us out to Venice Beach, never made eye contact with me, and we were just in this weird awkward silence the whole time. I would ask him what is wrong, what is on his mind, and if needs me to call for help. No answer. I knew something was bad. Of course, in my mind, I was running various scenarios in my head what my next move was. We went back to his car, and he was taking me back home.

Before we got close to my place, he let out a deep sigh and says, “I have something to tell you.” Of course, my insides were screaming at this point. He says, “I… I don’t deserve you. You have a lot to offer someone to make them happy, and I am not that person….” He pauses, sighs again, and then says, “You know why I was not responding early on? Because I was in mandatory anger management counseling, and was having trouble coping with life.” My eyes grew wide, and I asked what happened. He said his last girlfriend got on his nerves over something they argued about, and in turn, it frustrated him so much that he nearly choked her to death. Because of what occurred, he was in court-ordered counseling for the next few years and had to check-in with someone three times a week. He felt he was ready to date again because he felt he mentally moved onto becoming a better person.

By the time he pulled up to my house, he finished everything he was saying. He asks, “What do you think I should do? What advice do you have for me?” I told him calmly, “I admire your courage to tell me the truth. I think the best move from this point is to remove your dating profile, finish your healing, rebuild yourself, and maybe try again when you feel ready.” I said bye to him, went back in the house, and I literally just sat in my bed just in a weird stupor because I could not believe what happened, and thanking my stars that nothing happened to me. Strange but true, he actually did write me a final email thanking me for everything, and he did take down his profile a day later.

#8

Image source: ThatOne1983, freepik

He asked me how much the bill was for his portion on our first date. I scan the bill and say just put in $15 and it’s fine, I’ll get the rest. He grabbed the bill out of my hand and proceeded to explain to me the exact amount he owed for about five minutes like I didn’t understand basic math.

Oh and I’ll throw in a bonus here. Another guy, first date. We met online so it was our very first time meeting. Met at the restaurant, parked close so our initial meeting was in the parking lot. He says hi, asks how the drive was and then told me that if I didn’t agree to f**k him after dinner he wasn’t going to bother with the meal. I got right back in my car and left.

#9

Image source: InfamousClown, fxquadro / freepik

She drove through a red light going 50 mph and totaled 2 cars. Almost k**led me.

#10

Image source: Skeets2680, standret / freepik

When he wouldn’t get out of my truck until I kissed him. I threatened to drive to the police station to get him out of my f*****g truck. Spoiler alert: there wasn’t a 2nd date.

#11

Image source: CaptainFartHole, freepik

It was the first date.
He brought his mom. .

#12

Image source: maximum-nothing-4106, romankosolapov / freepik

Prior to the date he told me he had a son. During the date he casually mentioned he actually has three children but two don’t count because “their mom is a b***h”.

ETA: some of yall are doing some mental gymnastics to excuse this man 😂 he meant what he said. I asked him to elaborate and he doubled down.

#13

Image source: ktsb, freepik

We went to a movie and as we got up she threw the popcorn on the floor. Flipped the bag and gave it a good shake. I said that wasn’t nice and she said they have people to clean up. I wish i had said something else but i sorta just went on auto pilot until i dropped her off. .

#14

Image source: OK_weird1229, Racool_studio / Freepik

She showed me two pictures of exes and asked where I would rank myself with them.

#15

Image source: Puree_Butterflies, user18526052 / freepik

So this is embarrassing in retrospect. Back in my second year of college, I was pulling an all-nighter at the same time as this very cute girl who I was friends with. We weren’t in the same place, but we kept messaging over facebook or hangouts or what have you the entire night. It was really nice just talking with her. I had been single for about two months, and was just getting over the break up. When dawn hit and our papers were finally done, she asked me out for celebratory breakfast.

I went looking kinda gross. I absolutely looked like I had just finished an all-nighter. She looked radiant and had clearly put more work into this meeting than I did. As our breakfast went on, we’re talking, laughing, and the caffeine is mixing with the satisfaction of completing my work for the semester, and I just feel like I’m in a really good place and I tell her as much. The sun is starting to fill the windows of the restaurant we’re in, and there’s this warm light everywhere. She smiles, looks coy, and asks me if I’m over my ex. I smile back, say that I am, and tell her that I’m already thinking of the person who I’d like to ask out next. She smiles even broader and asks me if she knows who it is, while touching me on the hand…

Still smiling I say, “I don’t think so, her name is Rebecca and she was in one of my history classes”. Distinctly, this was not the girl I was out to breakfast with.

The girl I was with, looked absolutely devastated. And I had no idea why. I think I said something like “I’m sad the semester’s ending soon, but I’ll see you in the spring!”. And thus ended what I would later learn was the first date with the woman who would later become my wife.

#16

Image source: JetPlane_88, cookie_studio / freepik

It was our fourth date.

*She* brought up the exes conversation (how many relationships have you been in, why didn’t they work out, etc.)

Without skipping a beat she told me she’d probably still be with her last partner but he left because she lied about taking birth control.

#17

Image source: _Justag1rl_, wayhomestudio / freepik

He asked me how many other guys I was talking to, and when I said no one else, he said “fine lie to me if you want, I’m talking to 7 other girls. It’s kind of a slow week for me because it’s usually like 15-20” LOL. I laughed because I thought he was joking, and that pissed him off even more. He told me he could have anyone he wanted, and he left.

#18

Image source: Kindly-Question-7357, gpointstudio / freepik

When he told me I reminded him of his sister and then wouldn’t stop talking about her.

#19

Image source: Cat_tophat365247, freepik

Went on a dinner date at a guys house. He surprised me and had invited his parents over and that was awkward enough. Then, in the middle of dinner, he got down on one knee and proposed…..it was our FIRST date. I just got up and walked out. Thank God I had driven there. At that point, I would have walked home if I had to, though.

#20

Image source: GingerSnaps94, freepik

First date. Starbucks was closing and he asked me if I wanted to continue the conversation in his truck. I happily agreed- as soon as we got in, he turned the truck on and took off down the highway. He said he’d take me back when I proved to him what my mouth could do while whipping out his p*nis.

Basically got kidnapped on the first date. Oh yeah, and he was a middle school resource officer 🙃.

#21

Image source: FriendOfSelf, peoplecreations / freepik

I was on a first date with a young Mormon lady, we were in our mid-twenties. She was telling me a little bit about her beliefs, about the seven stages of heaven and how most people can get to at least the first level of heaven. Then she started talking about sin, and how you can see deeper sins in the color of people’s skin. That darker skinned people have more inherent sin, so cannot go to heaven. But, if they repent their sins, their skin will become pure and white, and then they can at least enter.

As she was explaining this to me, her speech got slower…and slower…you see, I’m Latino. Needless to say, we didn’t make it to the first base of heaving.

#22

She littered fast food wrappers out my car window. I made a u turn and took her home instead of the movie we were supposed to go see.

Image source: truffleddumbass

#23

She showed up wearing a (dirty) white crop top and started playing with her exposed belly button in the middle of our dinner date and then proceeded to say out loud with people surrounding us “Ew What the hell is that in my bellybutton?!”.

Image source: poetadin

#24

Image source: kikihippiex, katemangostar / freepik

When he said he traveled to Africa often for work. I lived in Africa for a bit and initially loved this…it was something we had in common. Until he said he doesn’t think people in rural villages in Africa should have access to clean water or electricity because “someone has to pay for it”. After back and forth for a bit I got up and left.

#25

Image source: itso-complicated, zinkevych / freepik

He asked me to go to a movie, then pulled up in crocs and pjs. Said we were gonna go to his house instead of the movie theatre. Then proceeded to tell me he doesn’t actually have his drivers licence.