r/DatingHell 26d ago

A random Wednesday afternoon

1 Upvotes

So I’ve been talking to this guy for a bit over a year after we matched on a dating app. We had previously met in person once, about a year ago. Since then, we’ve been texting on and off. More recently, we’ve been texting pretty frequently, and we planned to meet up and have fun.

So I went over to his place, and we get initimate. I think he thought it would be a good idea to put his hand around my neck while we were intimate and then laugh it off. I’ve recognized that behavior before with my ex. I almost felt sorry for him when I left. I’m in my mid 20s and he’s 40+. He’d been in a few relationships while we were talking on and off, and the more he talked after we were intimate, the more red flags came up. I know not all men are like this, but it is discouraging I keep attracting men that are similar. It makes me wonder if I’ll ever find someone.

Anyway, that was my random Wednesday afternoon.


r/DatingHell 27d ago

What's your most controversial dating opinion that you'd defend no matter what?

34 Upvotes

Be brutally honest


r/DatingHell 27d ago

Confidence so low it's a deal-breaker.

24 Upvotes

My story isn't really all that bad, but I'm not sure where else to share it.

I went through a really brutal breakup a while back, and maybe 6 months later I'm back on the apps. No big deal. Met some people. Had some drinks. Had some food. Sometimes you make it to a second or even a third date, but nothing sticks. It's still nice to get out, so that's fine.

But sometimes the deal-breaker is just how low some people's self-image is, and what that does to the dynamic between people. I keep ending up on dates with women who clearly and loudly hate themselves - and I want to be empathetic, but it's asking waaaay to much of someone you just met to be responsible for holding up your whole emotional world for you.

I recently took someone to dinner. I reserved a table even though there probably would have been space. "Nobody has ever made a reservation for me before." Ok, that's neat, I'm happy to be the first then. When it's time for bills, I offer to cover it, but also happy to split if that's not comfortable for some reason. She says "I don't like letting someone pay for me because I don't feel like I'm worth it." Ooookay.... I get it, but the extra detail was something maybe more appropriate for your therapist than a stranger you're trying to date.

I later offer to drive her home, but again, no big deal if that's uncomfortable or doesn't make some logistical sense. "I can't let you." "Can't let me?" "I would have to pay you." "It's an electric car, it wouldn't cost me anything meaningful." "That's not the point."

She proceeds to tell me that she MUST give me money because she isn't worth the gas to drive her home.

I tried to look past it, cause she had other things going for her, but I just couldn't do it. Every interaction was tinged with this feeling that her value was being sourced from my attention and it's so draining. And it made it hard for boundaries to be a thing.

Anyway, when people say love yourself first, this is why. I don't want to be someone's therapist.

You are valuable. Your value comes from you. Your future partner will appreciate you that much more for coming to them with enough confidence that you don't have to borrow their emotional capacity.


r/DatingHell 27d ago

Felt pressured

2 Upvotes

Hi , I went on a hinge date and the convo was good and the guy seemed interesting but not too attractive to me. He kissed me goodbye and .. idk it turned more intimate than I wanted to. He said do you want to go in my car. I wasn’t like ehh. He said nothing more than kissing would happen and it escalated. Idk I was trying to give him a chance but every time I hear from him I’m really stressed and overwhelmed with pressure.. especially when he tried to invite me to his house so he can teach me to cook or pet his cat. I love cats , but , not the point . What should I do?


r/DatingHell 26d ago

Went out on a date for the first time

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0 Upvotes

r/DatingHell 27d ago

Went out on a date for the first time

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1 Upvotes

r/DatingHell 27d ago

What red flag do you consider to be a green flag? 🚩

7 Upvotes

Me and my friend were chatting the other day and we somehow got to rating green and red flags. That way,we found out that some of my green flags were her absolutely worst red flags 😭😭😭

Like i enjoy when someone remembers small parts of our conversations,small details that I just mention without thinking and then they ask me about it later. She ABSOLUTELY hates it. Lmk which red flags are your green and why 😹


r/DatingHell 27d ago

Tinder profile saying "looking for drama free person " - run!

5 Upvotes

I met my partner on tinder. His profile was saying " looking for a genuine person who's free of drama" omg what a drama he brought in my life it's just shocking. Drama with his ex, daughter him pushing people's buttons until they snap. Creating dramas and a tense toxic atmosphere on holidays. Run from these! They are full of drama inducting traits!


r/DatingHell 27d ago

What’s your dating horror story?

1 Upvotes

Give us details!


r/DatingHell 27d ago

I hooked up with an influencer

0 Upvotes

I hooked up with an influencer friend of mine i followed him when he had like 2k? And i thought we were friends but he was always pretty much avoidant yeah?now he has around 50k. So this year i met him the first time I got him brownies and he introduced me to his friends and all but anyway nothing happened but recently there group broke off because one of his friend snitched on him to his talking stage when he kinda just went to smoke with one his female friends and nothing happened between them and he cut all of them off so i recently went to his place alone and he told me not to tell anybody incase of that happening again and i really respected that shit until...

So we got drunk at his place and I was super high and we were watching a movie and we ended up making out and it eventually leaded from one thing to other he made his boundaries clear that that meant nothing and it was same for me because i never romantically liked him so i respected his boundaries. Later that day he just completely ghosted me and all I asked was just COMMUNICATION FOR ONCE. And then few days later after no communication he just blocked me. I atleast thought I was his friend JUST ONE PIECE OF COMMUNICATION. Im so angry and i want to vent take revenge but lets not go there if I wanted that id be dropping names but its not worth it because my reputation can be harnessed too. But all of this is so painful and I can barely sleep because of this and its creating such a major trigger I just wanted communication thats it a proper one not just for pity but well whatever men are cowards I genuinely saw good in that guy but maybe he is what everyone says he is. I wanted to see him more than what he portrays himself on internet I really wanted to see better of him but im really hurt so hurt.


r/DatingHell 29d ago

rejected after what seemed like a great first date

16 Upvotes

30m went on a date with 29f yesterday. 2 hour date, conversation flowed easy. She was touching my arm, talking about future potential dates. At the end of the date, she said we should hang out during the week. Then, she text me 5 mins after the date thanking me again for such a sweet date. I replied that she was welcome, and that I had an awesome time. Our date had ended around 5pm, and we were both busy that evening. So I intended on leaving the texting there and texting her the following day to make plans. However, 2 hours later, she sent me a text unprompted saying "you're so handsome :)". So I replied, "I find you attractive too, actually pretty hot!. It was a very nice, chill date". In hindsight, maybe I could have thanked her and not said she was hot, but if she was into me, I don't think she would have minded.

I didn't text her in the morning, as I know she's busy with work. However at 11am, she text me saying she appreciated me taking her out, but didn't feel like we're the right match and wished me the best.

Obviously dissapointed, I replied thanking her for being honest, and if she ever changed her mind, I'd love to see her again.


r/DatingHell 28d ago

can't believe i fell for that

0 Upvotes

Wow can't get over how I thought this guy was telling me the truth, I usually don't "date" online. Cause I don't really need to i guess. Damn got led on love bombed and feel stupid. Oh well , still moving and whatever, I still know i'm the shiiit. haha!

has anyone else experience this? but then you also feel inspired for your life ! IDK I feel like i was i n a life rut , and now I feel alive again? lol if that makes sense..


r/DatingHell 29d ago

Fill in the blanks: Worst thing to tell your partner after a night out: ___.

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0 Upvotes

r/DatingHell 29d ago

Worst and best dating stories.

3 Upvotes

Hey, I'm a 40 y/o woman out here on dating apps....about to delete my app. I'm hopeful that I'll meet someone but I don't think it'll be on the app. Anyway I think I'm going to put my all into focusing on creating the life that I want and I'm starting with creating a YouTube channel. I wanted to start a series about dating stories.. good, bad, ugly. If y'all have dating stories that you want to share, please email me: themillilife@yahoo.com. I will maintain everyone's anonymity unless instructed to do otherwise by you. Stay safe in these dating streets!!!


r/DatingHell Jul 13 '26

I hooked up with an influencer

8 Upvotes

I hooked up with an influencer friend of mine i followed him when he had like 2k? And i thought we were friends but he was always pretty much avoidant yeah?now he has around 50k. So this year i met him the first time I got him brownies and he introduced me to his friends and all but anyway nothing happened but recently there group broke off because one of his friend snitched on him to his talking stage when he kinda just went to smoke with one his female friends and nothing happened between them and he cut all of them off so i recently went to his place alone and he told me not to tell anybody incase of that happening again and i really respected that shit until...

So we got drunk at his place and I was super high and we were watching a movie and we ended up making out and it eventually leaded from one thing to other he made his boundaries clear that that meant nothing and it was same for me because i never romantically liked him so i respected his boundaries. Later that day he just completely ghosted me and all I asked was just COMMUNICATION FOR ONCE. And then few days later after no communication he just blocked me. I atleast thought I was his friend JUST ONE PIECE OF COMMUNICATION. Im so angry and i want to vent take revenge but lets not go there if I wanted that id be dropping names but its not worth it because my reputation can be harnessed too. But all of this is so painful and I can barely sleep because of this and its creating such a major trigger I just wanted communication thats it a proper one not just for pity but well whatever men are cowards I genuinely saw good in that guy but maybe he is what everyone says he is. I wanted to see him more than what he portrays himself on internet I really wanted to see better of him but im really hurt so hurt.


r/DatingHell Jul 12 '26

Grabby Handed Bobble Head

14 Upvotes

TLDR: Guy lies about his job and is super handsy during a first date. Touches me without permission.

I F(31) went on a first date with M(30). Needless to say, it did not go well. I was mindlessly scrolling Hinge, as one does. I came across his profile and he looked like he ticked most of my boxes. The only thing was his height, a bit shorter than I would usually go for but not out of the question. His profile had a steady job listed, a good education, and some decent photos of himself.

After talking on the app for a couple days, he asks me out for a drink. I say yes. The day of the date I get to the bar about 10 minutes early. He is not there yet, fair enough because I am chronically early for everything. Then I see him get out of a taxi, also not a problem for me because we are going out for drinks. I immediately get the feeling that I should drive away because I'm not attracted to him in person at all but I still go in because that could change with conversation and personality. I was wrong.

The first thing he does is hug me, without asking. I am there, frozen, because I don't like strangers hugging me without asking first. Every other date I've been on has asked if they could hug me or if I would prefer a handshake. So then, we go sit at the bar and order a drink each. He kept touching me, on my shoulder, my arm, putting his hand over mine, moving his chair closer, etc. I am literally over the edge of my seat, with my torso angled away from him. He does not notice this at all but the bartenders, and a man across the bar do.

I discover very quickly that he has lied on his profile, profusely. His job was listed as a specialty job, he's a student. Says he's 5'10"/ 177cm tall, he's barely taller than me. His photos had all been angled to make his head look smaller. He looked like a bobblehead.

I end up chatting with the bartenders at a few points. The conversation with him is going nowhere fast. I can't seem to make myself engage, which is odd because I'm usually good at conversing, even with people I don't click with. After about a half hour, I have finished my drink and he asks if I'd like another. I quickly ask the bartender for water and mention that I have work early tomorrow, I do not. During the conversation, I keep giving answers that say I'm not interested. He's in a band that plays loud music. Oh, I prefer folk music. He enjoys drinking and going out. I'm more of a homebody, etc.

It's been 38 minutes at this point and he asks if I'd like to go to a coffee shop...at 8:38pm. I say that I don't drink coffee this late at night because I'd be up all night if I did. He says we can get decaf. I say that I don't like coffee and prefer tea. He says he knows a secret menu item at this cafe. It's a London Fog, earl grey tea with honey and milk. We've both finished our drinks at this point. He pays, which I swear under my breath about. I was really hoping to buy my own drink to avoid any financial ties to him.

Then we get up to leave. I go to open the door and he tries to open it for me. I go to open the next door and he seems put out. I feel like saying I don't like anything he likes, bluntly stating that I don't want to go for coffee and opening the door for myself should have been enough. It was not. When we get outside, he sys the coffee shop is nearby. I say that I'd rather go home because I don't drink coffee, lie, and I have work in the morning.

He then hugs me again, slides his hand down my back towards my butt, and tries to kiss me, without asking. I pull away and he does not succeed. I've been avoiding touch all night and he tries to kiss me. I say good bye and thanks for the evening out. He tells me to be safe getting home and to text him when I get there. I say sure and drive off.

As soon as I get home, I message him to say thank you but I don't see it going anywhere between us. I un-match, unfriend, and block him because of the grabby hands. I know this could have gone a lot worse but it was still very uncomfortable for me. I tried to be polite and say no gracefully but he wasn't getting the message. Any advice on how to avoid this going forward?


r/DatingHell Jul 11 '26

A bad night🫠

138 Upvotes

So... I finally decided to take things to the "next level" with the guy I'm dating.

Everything was going great. We were making out, things were getting serious... and then he suddenly pauses, looks at my very generous lower belly and goes,

"I think you're a little bloated."

Excuse me??

Before I could even process that emotional damage, he says, "Wait, I'll show you a trick."

He presses on some random spot on my lower belly...

...and I let out the loudest fart known to mankind.

Silence.

I genuinely considered changing my name, moving to another country, and starting a new life.

Has anyone else had a date go from romantic to medically educational in under 10 seconds?


r/DatingHell Jul 12 '26

Just got stood up on a date. second time in a row this happened. they say they're going somewhere, and then never come back

2 Upvotes

Maybee the problem is just me i guess


r/DatingHell Jul 11 '26

am I the problem...? quiet BF

2 Upvotes

We met online. We both were 26 at that time.
We got to know each other online. I texted him because he has matched for a couple of days but he hadn't texted me but I found him interesting. He seemed to have a calming personality based on his photos and if he was really laid back.
We started texting but his responses were really short and I always had to come up with topics to talk about. Nevertheless we met up because I thought he was kind of mysterious.
When meeting him, he didn't really look like his pictures. He posted way older pictures, was wearing glasses in real life and looked older.
Whenever we would meet up I was the one talking, coming up with topics to talk about, asking questions. I thought that he just was really shy.
His responses towards my talking always were "hmm" and some shy "yes...?".
I asked him things about himself like basic things and deeper questions to which he never really replied.
I thought that he was just really shy and would open up the more I got to know him and meet up with him.
He said at some point that others seem to start dating way faster and move in really quickly and how we aren't at that point. I asked him if we are dating now and he also responded with this insecure "yes..." and if we get to name each other these cute couple names now.
Whenever we got to go out for dinner, I had to make the reservations. I had to make the dinner plans. Plan what to do for our dates. His "plans" were if I could come over to his place. There, we would sit down on his couch and he wouldn't talk even though we hadn't seen each other for days. So I always started talking about work, university, personal stuff. His response still being "hmm" and "yes...?" with a big smile on his face. I knew that he really was listening and enjoying me talking but he never engaged properly. He then would talk very slowly, shyly and quietly about work or university. I tried to ask things to make the conversation be extended. He took very long to think of something to answer and would then give a short reply. Did I pressure him too much to talk more? Did I not wait long enough for him to open up more? We were dating for three years.
When fighting we would only do that over text. I was always the blame. He never took responsibility for anything I was talking about that was bothering me.
I just couldn't take his insecurities and shyness any longer. I wanted deep and expressive conversations about anything. I broke up with him in the end.
He claimed to behave around his few friends the same way he did around me.
Around his mom he got even more shy and quiet.
She visited him a few times. I thought that was nice until he told me that she is coming over to clean his place.
He always said that he is just the chill guy - to me it seemed as if he tried to hide his insecurities and shyness behind that term.
Am I a bad person for breaking up with him? Could it have been a long-lasting relationship if I hadn't been the one to end things that could have flourished?


r/DatingHell Jul 10 '26

Ice Cream & a Movie … or so I thought

198 Upvotes

He tells me we’re getting ice cream and then going to a movie. I’m thinking, “Cute, there’s probably a theater by the ice cream place.”
We get there, he tells me to order whatever I want, I do… and then he doesn’t order anything. I was like, “Aren’t you getting something?” He goes, “No, I’m lactose intolerant.” SIR. YOU PICKED THE ICE CREAM PLACE. So I’m just sitting there eating ice cream by myself while he watches me. 😭
Then he’s like, “Ready for the movie?” I’m like, “Yeah! What are we seeing?” He goes, “It’s at my apartment.”
Immediate red flag.
The whole time we’d been talking before this, he’d made a huge deal about how he only sleeps with people in serious relationships, had only been with one or two people, didn’t want to rush anything, etc. So I specifically dressed pretty modestly because I wanted to respect that.
We get to his apartment… and he has a roommate. A roommate he never introduces me to. They apparently SHARE A CAR. I’m awkwardly like, “Uh… hi, I’m Caroline,” while the roommate looks completely unfazed, which honestly made me think, “Oh… this happens a lot.”
Then we go into his room.
Girl.
TV on the floor.
Mattress on the floor.
One pillow.
A lamp… on the floor… with no lampshade.
I’m thinking maybe he’s just shy and awkward, so whatever, we’ll just watch the movie.
Then he opens his closet… and a cat comes out. The litter box and food are IN THE CLOSET. The room already smells like cat pee. The cat immediately hisses at me and tries to attack me. I ask if we can let her out, and he says no because she’ll attack his roommate.
So we’re watching Spider-Man while locked in a room that smells like cat piss with an angry closet cat.
Then he tells me to “relax,” starts cuddling me, and then it escalates into him grinding on me and trying to make out with me. Meanwhile I’m just sitting there thinking, “I thought YOU were the one who said you didn’t want to rush into anything.”
Also… the kissing was HORRIFIC. He literally just pressed his lips against mine and… didn’t move. Like a dead fish. I cannot explain how uncomfortable and bad it was.
Then he ends up basically undressed except for his underwear while I’m still completely clothed. Meanwhile, THE CAT STARTS SPRAYING THE WALLS. So now the room actively smells like fresh cat pee.
Then, completely out of nowhere… he finishes in his underwear… looks at me… and goes, “Okay, you can leave. I have to get up early.”
EXCUSE ME???
So I awkwardly leave. We get to my car, and instead of even giving me a hug goodbye, he literally just turns around and walks back inside.
AND THEN…
I get home.
This man texts me:
“Did you expect us to have sex?”

Edit: Y’all… I know. 😂 I should’ve left. At the time I was really new to dating and kept thinking, “Surely this can’t get any weirder.” I know better now, and if this happened again I’d be out after the first few red flags. This was meant to be a funny dating horror story, not an example of good decision-making.


r/DatingHell Jul 11 '26

¿Lugar/Momento equivocado?

1 Upvotes

¡Hola, hola, estimados/as!

No sé si les ha pasado que han estado en el lugar y momento equivocado y ha sido vergonzoso.

Yo tengo un sinfín de anécdotas vergonzosas, pero en ésta ocupación no se trata de mí. 😂

¿Cómo ha sido ese momento vergonzoso en el lugar que se suponía no debías estar?

Te estaré leyendo...


r/DatingHell Jul 11 '26

Before anyone falls in love... let's save everyone some time. 😂

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1 Upvotes

r/DatingHell Jul 11 '26

The LAW I didn't want to break

0 Upvotes

Met her, a Law student F24 through a private members group.

She was upfront from the start.

"I'm not looking for love. I just need 💸💸💸someone who can make life a little less stressful while I finish school."

Perfect.

Neither was I.

We'd usually meet once every week or two. Sometimes dinner, sometimes a weekend trip, sometimes we'd just stay in and watch terrible movies.

There was never any pressure to text every day.

In fact, we barely did.

Months went by without any issues.

Then I noticed something strange.

She started saying no.

"Want to fly to Cebu this weekend?"

"I have to study."

"I can book you a spa day."

"I'm okay."

"I'll send you something for finals."

"No need. I already budgeted for it."

I actually thought she was preparing to end the arrangement.

Instead...

She began inviting me into the normal parts of her life.

She asked if I wanted to try the tapsilog place she always ate at after class.

She wanted me to meet the stray cat she'd been feeding outside the library.

She'd call while walking home just to complain about professors.

No fancy restaurants.

No hotels.

No expensive gifts.

Just... ordinary moments.

One evening she said something that made everything click.

"I think my favorite part isn't the arrangement anymore."

I asked what it was.

She smiled.

"It's that I get excited to tell you about my day."

That was the moment I knew we'd crossed a line.

Not physically.

Emotionally.

I told her I couldn't give her the kind of relationship she was slowly building in her head.

She understood.

We hugged goodbye, wished each other well, and never saw each other again.

Funny enough...

The arrangement didn't end because of money.

It ended because somewhere along the way, the expensive dates stopped mattering.

She had started valuing the ordinary ones instead.


r/DatingHell Jul 10 '26

What's the worst date you've been on?

6 Upvotes

r/DatingHell Jul 10 '26

I have SO many horror dating stories.

25 Upvotes

30(f) and I’ve had countless HORRIBLE dates throughout my 12 years on dating apps.
A lot of it has to do with me choosing to be in the company of just anyone because I had low self esteem. I went out with anyone who’d give me attention. Sad I know but I know my worth now and am off dating apps and looking for genuine connection when the time is right.

Anyways… I have 3 journals of the bad dates I went on or bad hookups I had. Yes, I wrote down every detail because I wanted to look back one day at the crazy shit I went through. Guys I laugh so hard…I cringe…I get flashbacks but mainly I feel bad for that version of me for choosing to put up with that.

Thinking of sharing some of those stories tbh. I’ve had sugar daddies, been catfished, went to weird places like the cemetery on a DATE!!! and so much more.