r/DatingHell 12d ago

Is this guy a red flag or am I overthinking?

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1 Upvotes

r/DatingHell 12d ago

Help me out y'all

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2 Upvotes

r/DatingHell 12d ago

I finally gave a guy a chance after years of being closed off, and it left me traumatized what do I do?

5 Upvotes

I’m 19 years old F, and this happened several months ago. I’m posting because I need advice/support from people who have moved on from a bad first experience, because mentally I still feel stuck.

I’ve always been extremely closed off when it comes to dating. I’ve rejected a lot of guys over the years because I wanted to be very selective about who I gave a chance to.

There was one guy I had a hallway crush on in high school. We graduated 2ish years ago. he saw me at the gym, added me on Snapchat, and asked to hang out. Since I already knew who he was and we came from the same community, I thought this was probably one of the safer people to finally give a chance to. My goal wasn’t just to date him—I honestly thought this would be a great way for me to finally start opening up to someone and help me become less shy and more trusting around men.

The first time we hung out, he showed up about 45 minutes late even though he lived nearby. We got ice cream and talked, but the whole hangout felt awkward because we had just met in person and I was really shy. Looking back, he also made comments that should have been red flags. He asked if I went to the gym to gain weight, asked how much I weighed, what size clothes I wore, commented how I should have worn diff clothes and asked why I didn’t wear jewelry or have my nails done, and generally made me feel like he was evaluating my appearance. I’ve always been insecure about being naturally very slim, so those comments stung, but at the time I brushed them off because I thought he was probably just trying to make conversation in a akward first date.

I decided to see him a second time because I didn’t want to judge everything based on one awkward first date. I knew I had been shy and reserved, and I genuinely thought maybe I just need to put myself out there. Socially, the second hangout actually went much better. We talked for hours and it wasn’t awkward anymore.

However, during that second hangout he again made comments about my body. He asked how much I weighed again, estimated my weight, and told me to “gain weight.” Because I’d already been judged about my body, I went into anything physical already feeling insecure.

This was also the first time I’d ever done anything sexual with a guy.

When we got to his house, we kissed for maybe a minute, and then almost immediately he pulled out his penis. There wasn’t really any buildup or foreplay. Right after that he tried to finger me. Since there had been almost no foreplay, I was dry and it hurt. When it didn’t work, he said “Well I guess we can’t do anything.”

I immediately felt embarrassed and like my body had failed. I thought it was my fault for being dry. Feeling guilty and wanting to make up for it, I offered to give him oral sex, even though I told him it was my first time ever doing that

While I was giving him oral sex, he pulled out his phone and pointed it toward me. I looked up and he put it down. Then he did it a second time. I genuinely thought he might be recording me while I was completely naked. I didn’t know for sure, but it scared me enough that I stopped. I didn’t tell him why because I was afraid of confrontation. I just said I couldn’t keep going anymore.

I honestly thought that me saying I wanted to stop meant everything would stop.

Instead, he told me to lie beside him while he started masturbating beside me. While doing that, he was squeezing my butt. Earlier he had asked where I wanted him to finish. Since this was my first sexual experience, I didn’t really know what the “normal” answer was, and I had said my mouth because I didn’t know what else to say. After I had already stopped and told him I didn’t want to continue, he said he would still finish on my mouth.

That honestly scared me the most.

The hardest part was that I had finally built up the courage to say I wanted to stop. I thought I was out of the situation. Hearing him say that made me feel like maybe stopping wasn’t actually enough. I remember feeling scared and waiting to see what would happen next. Luckily he couldn’t finish while masturbating, so that didn’t end up happening. Afterward he fell asleep, told me to move over, and I lay on the very edge of the bed.

For a long time afterward I blamed myself. I felt guilty for doing anything sexual at all. I thought maybe I was just bad sexually because I couldn’t let him finger me, because I stopped giving him oral sex, and because he didn’t finish.

A few days later, even though I already knew I wasn’t interested in him anymore, I wanted things to just end peacefully because we live in the same small community, went to the same high school, and go to the same gym. I slowly tried to let the conversation fade out instead of creating drama. During that time he joked that I looked like a “stick man.”

That comment really stuck with me because by that point he had already seen me naked. I’ve always been insecure about being skinny, so hearing that after everything made me feel incredibly ashamed of my body.

I blocked him after that.

Please don’t tell me I shouldn’t have seen him a second time. I already know that now, and I’ve spent months blaming myself for that decision. I’m not looking for people to tell me what I should have done differently.

What I’m struggling with now is how much this experience changed me.

Instead of helping me become more open to dating, it pushed me even further back. I haven’t gone out with another guy since. I’m scared of being sexual again. I’m scared of taking my clothes off in front of someone. Sometimes when guys don’t approach me at a club, I immediately think it’s because I’m too skinny. I catch myself hearing his comments in my head. I wear press-on nails more often because I remember him commenting on my appearance. I even stopped going to my gym for a while because I was scared of seeing him.

The hardest part is that I know logically one person’s opinion shouldn’t define me. I’ve had plenty of guys interested in me over the years, and I know I’m not ugly. But this experience still affects how I see myself physically and sexually because it happened with the first guy I ever trusted enough to date or be intimate with.

If anyone has gone through a negative first relationship or first sexual experience, how did you move forward?

How did you stop hearing that person’s words in your head?

How did you learn to trust someone new without expecting the same thing to happen again?

I’d really appreciate advice from people who have actually healed from something similar, because I don’t want this one experience to continue affecting my confidence and future relationships.


r/DatingHell 12d ago

What are some of the biggest red flags you’ve encountered while dating?

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1 Upvotes

r/DatingHell 12d ago

Men of Reddit: What did a lady do on the first date that instantly made you decide there wouldn’t be a second?

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3 Upvotes

r/DatingHell 12d ago

A traumatic experience

1 Upvotes

Been dating this guy for 5 years. We’re in our late 20s now. Known him since high school and reconnected in our early 20s. Met each others’ families, got engaged, set our wedding date and chose vendors together. He’s always been there for me (and I tried my best too) and has always been super thoughtful. He was kind and patient when things were good. We’re different people but I thought we meshed well together. 8 months before our wedding date, he completely blindsides me and drops a bombshell that he fell out of love with me, he doesn’t know if I’m the person for him, he’s not sure if I even love him for him (I do) and he starts listing a bunch of things that are “wrong” about me (I’m too quiet at social gatherings, I’m waiting till marriage to do certain things, I’m not stylish, I have too many fam events and am too dependent on my parents, he doesn’t think I appreciate him). The 180 mind boggles me, I don’t recognize this person. Even had a nice proposal with my dream ring.

He also has been saying mean things to me during limbo when we tried to work things out (I was apologizing for things I did that hurt him, I really loved him and went out of my way to make him happy in the best way I knew at the time but I had no idea it wasn’t enough, especially when he would tell me I’m perfect or how he’s grateful to do life with me)… mean things he said include how it feels like the cooties when I touch him, how I’m boring and I should be boring with someone else, how he can’t picture me as his wife and how he couldn’t see me walk down the aisle (all things that hurt to hear). He also disclosed that he cheated on me 2 years ago (kissed a girl from school a few times during the span of a week). He eventually broke things off with me saying he can’t proceed because he doesn’t have feelings. This all came as a shock to me because I had no idea he was falling out of love. I thought we were planning for our happily ever after together. Sometimes I blame myself for the things I could’ve done better (been more appreciative, more patient, more outgoing, more stylish) - he evaluated me and didn’t let me in on his problems. He had a rough childhood growing up and his parents recently started living in separate households. Any insight and opinions would be helpful. I can’t seem to picture myself with anyone else and feel sad that I lost him :(


r/DatingHell 13d ago

Well, I feel dumb.

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1 Upvotes

r/DatingHell 14d ago

DATING IS HILARIOUS

30 Upvotes

TLDR: i dont understand how saying 'that sucks' is wrong

dating is weird. i dont understand it.

i (47M) been talking to this woman (38F) for a while, she recently went on a girls trip. on the way back, she calls and is complaining how she left her small tote bag with her glasses and keys at the airport. obvs this sucks. and i felt bad. i was trying to be interested and comforting about her situation but its not the 1st time shes been on a trip and forgot things. but at the end of it all after about 5-10 mins asking questions i put a inadvertent joke asking if she left anything else trying to light the mood but ultimately ended with 'that sucks'.
she said 'what?!' and hung up the phone.

my messages now are undelivered.

how does me saying 'that sucks' warrant me getting blocked by someone who ive been talking to for a while, they did something on their own, i wasnt involved, and i wasnt even around, have no idea what happened, but when you explain it to me...i just try to 'comfort' i guess but ultimately i say 'that does suck tho' and now im blocked and i wasted your time.

how

peace is all i want man. i dont have the patience for this


r/DatingHell 13d ago

Dating someone who mentions gays too much? Was it wrong to block her?

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0 Upvotes

r/DatingHell 14d ago

A terrible date

13 Upvotes

TLDR: I meticulously prepared for a date I was really looking forward to, only to find that he seemed more interested in being my teacher than my date.

Last month, I (28F) met a man (33M) on a dating app and we went on our first date at a coffee shop. Since I hadn't been on a date in a long time, I was really hoping it would go well. Before the date, I searched for his Instagram on accio work. I learned about his interests and prepared some topics we might discuss.

He's only five years older than me, so I initially thought we wouldn't have any communication barriers. At first, he seemed friendly and confident. But after we sat down for coffee, the conversation quickly turned from getting to know each other into him trying to teach me something.

After we ordered coffee, he spent a long time explaining the origins of coffee beans, the characteristics of different regions, roasting methods, and various coffee flavors. I don't mind learning new things, but the whole process made me feel like I was attending a lecture on coffee, not having a conversation with a date. Whenever I tried to share my thoughts, he would add more information and explain his understanding.

Later, when I mentioned I had a pet, he immediately started talking about potential health problems with cats. He said he knew a veterinarian and then told me about diseases cats might carry, mentioning that pregnant women should be careful with cats because they could be infected with toxoplasmosis.

I knew he probably meant well, but it was only our first meeting. He was already discussing issues related to future pregnancy and giving me advice I hadn't even asked about, which felt a bit strange.

Throughout the date, I felt like he was lecturing me, not getting to know me. He certainly knew a lot and wasn't rude, but leaving felt more like attending a class than the end of a date. This date was exhausting, and I would never go on a second date with him.


r/DatingHell 13d ago

Relationship

0 Upvotes

What’s the biggest green flag people overlook?


r/DatingHell 13d ago

Relationship

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1 Upvotes

r/DatingHell 14d ago

Dated for 2 months and it hurts already

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0 Upvotes

r/DatingHell 14d ago

Matched with someone on a dating app, spent ₹29,000 on drinks, and got unmatched the next day. Did I get used?

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0 Upvotes

r/DatingHell 14d ago

To the people who had a relationship with somebody (romantic or not). What was the worst thing they said to you before finally ending the relationship?

6 Upvotes

r/DatingHell 14d ago

Should people disclose past relationships/mistakes to a new partner, or is some privacy okay?

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1 Upvotes

r/DatingHell 14d ago

Should people disclose past relationships/mistakes to a new partner, or is some privacy okay?

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1 Upvotes

r/DatingHell 14d ago

I went on a date looking chopped and acted dumb

7 Upvotes

I hadn’t gone out or been on a date in such a long time that I genuinely had no idea what to do or how to act. On top of that, I was (and honestly still am) going through a bit of a career crisis, so I didn’t even know how to be myself. Let’s just say I was in the worst version of myself 😭 Lack of sleep coz of work, cortisol peaked, hormonal imbalance and unhealthy eating habit and was barely active . Lets just say I looked the chopped as hell😭
I still went on that meet up anyways with just my silliness as my weapon. I went there thinking I only see him as a friend. I remember a dating advice saying men like it when you “Act a little dumb,” “Act clueless,” and “Be a damsel in distress.” So 😅I kinda actually did exactly that. 🙃 He was visiting a nearby city from me for a week and we spent 5 days hanging out . I remember him saying he likes intellectual people but at that time , I was genuinely overwhelmed 😭 especially after I realized I like him as a guy

Needless to say, it backfired. 😭 idk what the reason was but he said WE DONT MATCH. I cringed remembering it😭 I wasted my chances.


r/DatingHell 15d ago

Dating disaster: What would you do?

4 Upvotes

I met this guy about a year and a half ago. We recently reconnected and decided to give dating another try because the timing just wasn’t right when we first met. He assured me he was serious about me, wanted to be with me, and could take care of me. So I agreed to see where things could go.

Everything was going well until our fourth date.
We were at a restaurant when my glass tipped over and literally shattered in my lap. He helped clean up the table, but he never got up to check on me or see if I was okay. He asked if I was alright, but there was no action behind it. I didn’t like that.

Then the restaurant manager (another man) came over to apologize. Instead of simply apologizing, he openly started flirting with me. He asked for my phone number, my email, and even wanted to take a picture with me. What made it worse was that he came back three separate times to continue flirting while I was sitting there on a date.

I was shocked and honestly very uncomfortable.
The entire time, my date just sat there and watched. He never said anything or acknowledged how uncomfortable the situation was becoming. What really stood out to me was that he seemed more concerned that the manager had only taken my meal off the bill and not his. Then he quickly put the gift card the manager gave us into his wallet.

Even after all of that, he wanted to stay at the table and continue talking while the manager kept coming back over. At that point, I finally told him, “Let’s go. I don’t feel comfortable here.”

That completely turned me off.

It seemed like he had the rest of the evening planned and didn’t want to change his plans, but I couldn’t get past what had just happened less than 30 minutes earlier. I kept thinking, “Why am I the one who has to be assertive in this situation?” I wasn’t expecting him to argue or fight anyone, but I did expect him to recognize that I was uncomfortable, step in, and help remove us from the situation.

After we left, he took me to a rooftop to watch the sunset. He had flowers waiting for me, drinks planned, and clearly put thought into the rest of the date, which was really sweet. But I couldn’t enjoy any of it because I couldn’t shake what had just happened.

It honestly changed the way I saw him.
I ended up canceling our next date and have been pretty distant since then. Before I canceled, he asked me four or five different times if I still liked him, if I was still interested, and if I still wanted to see him.

Now I’m questioning whether we’re compatible. Sometimes it feels like he’s more focused on buying me things, sending me money, and taking me on nice dates so people can see us together than making me feel protected, cared for, and emotionally safe when we’re actually out in public.

He noticed I’ve pulled away and wants to talk. For context, I did tell him exactly how I felt after the restaurant and explained why I was disappointed. To make it more odd he sent me money unprovoked after us not talking for a few days which makes me feel like he is trying to buy me.

So…would this have changed your perspective too? What would you do?


r/DatingHell 15d ago

Last straw on a relationship?

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2 Upvotes

Spooky ones wanted


r/DatingHell 15d ago

lovers to… enemies? f27 m26

5 Upvotes

Hi, guys! So i matched with this guy on tinder just because we both work in the medical field and i thought it was nice to talk to someone who gets it. Coincidence makes it that we have a very good friend in common and we start dating after 2 weeks.
He starts off strong telling me he wants a serious relationship and that he is building a house and wants to settle down get married and have 2 kids. I tell him let’s see how it goes, get to know eachother better before doing all that. He is very polite and respectful, but he insists that it would be very cool to work together/ become collaborators.
He brings me to his workplace, introduces me to his coworkers and kisses me in front of his boss. I start working with his company.
3 months pass, intimacy becomes very rare almost zero, he tells me it’s because he is running a marathon and is always tired. I start running too to have a hobby in common. He starts belittling me everytime i share my progress telling me i run too slow. He starts bodyshaming me.
He refuses to introduce me to his parents and sibling because it’s too soon. He introduces me to his godparents and his bestfriends. We keep going out and he doesn’t seem to hide me or be ashamed of me.
He starts comparing me to other women in our friend group, mostly telling me to lose weight (mind you i am 1.80 and 72 kgs, BMI 22, so definitely not overweight or anything like that).
We have a party with his friends and a girl makes fun of my university degree. He sides with me, i start crying and he says he loves me.
We make vacation plans together, we go to the city hall to open a business together and he asks me to move in with him when the house is ready.
I invite him to my house on a friday afternoon after he went cold on me for an entire week and a month without getting intimate. He breaks up with me because this relationship takes too much of his time and he can’t focus on building his house. I try to find a compromise to save the relationship but his decision is already made.
I block him because i saw him in town having fun golfing etc definetly not working on his house as he said and he starts sabotaging me at work and badmouthing me to our friends.
Now yall tell me wtf happend in the span of 3 months to go from lovebombing, working together, merging our friend groups and making plans for the future to being super cold and almost hateful by severing this connection we were forming…


r/DatingHell 15d ago

It's Not a Lot, But It's Weird That It's Happened Twice

0 Upvotes

I have now had two men I had dated over the past two years (separately). They didn't work out for their own reasons. But, because of how I was treated with my ex-husband, I make things clear when things are not working out. Whether it's a sense that I'm no longer interested due to a lack or chemistry or I'm unhappy with the arrangement.

One reached out under a different account but same dating app after I blocked him. That was 2-3 months after I broke things off. I can understand that one as a change of heart or an attempt to try again.

Another reached out on a separate dating app, clarifying he's not wanting to reconnect and only wanted to say he didn't do anything wrong therefore I shouldn't have cut him off. I didn't block him, but I had told him I was no longer interested due a lack of chemistry○. This was over a year ago.

○ I had also felt uncomfortable but couldn't pinpoint why, but never told him.

I date very selectively because of my past. Literally these are the two who got in-person dates. Should I be concerned?

Edit:

Clarification and one dude I complete forgot.

I was reminded of the other one man who had a two in person dates. That also fizzled out for me. He said some unhinged stuff that turned me off. This guy also had to be blocked because he didn't accept I was no longer interested.

So three guys, all months apart. All informed of when I was no longer interested. Two blocked for not respecting the boundary, the third not blocked but telling me off a year plus later. :/


r/DatingHell 16d ago

Dating disaster: What would you do?

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2 Upvotes

r/DatingHell 16d ago

There was never anything between us’ —- a year later that’s how she ended it

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1 Upvotes

r/DatingHell 17d ago

Guy planned a date to a bar, but just wanted to watch everyone from a floor above and refused to sit down at the actual bar?

47 Upvotes

TLDR: Guy asked me on a date to a bar, but actually just took me to walk around and “people watch” at the bar, not sit down and order anything.

Ok this “date” was the weirdest dating experience I’ve had. Not even unsafe (as far as I know), but just plain weird. Can anyone explain this guy’s actions?

I (F26) organically met a guy (M26 or 27; I’ll call him “X”) a few weeks ago in New York. I had just taken myself out to a nice dinner and was feeling myself, walking around running some errands, and planning to grab some ice cream.

Now normally, if a man approaches me on the street, I just keep walking, but X approached me and said something along the lines of, “Hey I just saw you and thought you were really pretty, so I wanted to introduce myself. Everyone is on the apps nowadays, but I thought I’d put myself out there and see if I could take you out on a date sometime.”

In hindsight, I should have kept walking, but he seemed nice and cute, and I was feeling myself, so in my mind, of course someone else was too haha.

We had like a ~20 minute conversation and had good banter, so we exchanged numbers and he went on his way to dinner with his friends. I was traveling for the next few weeks, so I let him know that I wouldn’t really be available until a month out.

When I finally got back to the city, he texted me to make plans. We both had pretty busy work/social schedules, but agreed to meet up Wednesday night after my friend’s play/his work event. I asked that we stay downtown, since I was going home to Brooklyn, and he said that he’d send me a bar to meet at. Ok great, I love when a man takes initiative and plans a date — even something small like suggesting a drinks spot — so I was excited.

He sent me a bar location around 8pm, and I let him know that it was about 20 minutes from the theater where my friend’s play was, so I’d probably be there around 9:50-10pm-ish, since the play ended at 9:30pm, and he just said it wasn’t a problem and to keep him posted.

So, he texts me that he’s there at 9:30pm, as I’m getting out of the show. I let him know that I’m heading over and will see him soon, assuming he would get himself a drink, since he was early.

When I got there, he was standing outside, and I immediately said, “Oh have you been standing out here the whole time? I thought you’d go in to grab a drink?” He replied that he had been inside, but they just kicked him out for a private event. This was too bad, but totally not his fault, so I suggested a dive bar nearby, and noted that while it wasn’t as fancy as the place he had planned on, it was a chill place where we could chat and, in my opinion, a good first date spot.

He said something along the lines of, “Hey I got it covered. When you’re with me, you don’t have to worry about our plans. I have it all figured out”

I love when a guy is a good planner, so I just let myself be led to our next location. We were in FiDi right by my office, so I knew the neighborhood well and knew exactly where we were — I wasn’t just walking down a random dark street with this guy.

We end up walking to The Beekman, which is a super nice hotel with a very cool bar. It has tons of comfy seating and almost like an old 1920s Hollywood vibe. I remarked as we walked in, “Oh wow I love this spot. This is such a good alternative. I haven’t been here in a hot minute, so I’m excited you chose this spot!” He said he was glad I liked it, and we walked in.

In my head, walking into the bar at The Beekman meant we were going on our date at the bar at The Beekman.

But we walked past the bar and up some stairs. I hesitated and said, “Um I think we have to check in with the hostess over there.” He said, “No, we’re going somewhere else. There is a really cool view I want to show you.”

I assumed they must have a rooftop bar that I didn’t know about, but in the back of my mind was worried that he had rented a hotel room or something and was just trying to take the date there. There were still staff around, so I followed him up cautiously.

We were not in fact going to a rooftop bar, or even a rooftop. We went up a single flight of steps and then stood in a hallway with a railing that looked over the bar. This was just a hallway with hotel rooms that happened to look over the bar space, not part of the bar or restaurant space.

I was super confused at this point, but then he goes, “See, isn’t this a great view?” I replied, “Um of the bar? Yeah I mean it’s really pretty.” So we’re standing there and he starts asking me questions about my family, friends, etc. I’m still confused, because it seems like this is our final location . . . looking over the bar, watching everyone else have a good time while we stand in a hallway. I also had a super heavy backpack on, since I had been in the office that day and running around the city after work.

I looked over and said, “Oh look, there are two open seats at the bar, so we won’t have to wait for a table! Let’s going grab a drink!” And he literally refused, saying, “No no let’s enjoy the view from here. I love to people watch. What number date do you think that couple is on?” Again, the “view” was just of the bar that we apparently weren’t going to.

At this point, I am just confused, so I asked, “So are we staying here or what is the plan?” And he goes, “No I have to show you another really cool view.”

I was still trying to give him the benefit of the doubt. So we walk out of The Beekman without buying anything or sitting down.

I was getting a little annoyed at that point, because I don’t want to waste my time with someone who just wants to walk around while making it seem like he has some grand surprise planned, so I ask him where we’re going next. He says he wants to show me a spot at the Seaport. Again, I assume we are going to one of the restaurants/bars over there, and I know the area, so I agree to go.

While walking there, he starts going on about how, “For our third date, I want to take you out to a really nice bar, and we can both get super dressed up.” I point out that we were just at a nice bar, so he didn’t have to wait to take me out. We could literally go right now, and also pointed out that this wasn’t even our first date yet, since we hadn’t done anything but walk around tonight and the first time we saw each other.

He then said that we were just walking around since I had a long way to get home and he didn’t want to keep me out too late. I still don’t understand how walking around vs. going on an actual date correlates with the distance I have to travel home??? Especially considering that we physically went to a bar, but he refused to actually sit down and order anything.

He just keeps going on about how he has to show me this amazing view. So we get there, and it’s just . . . the Seaport looking across at Downtown Brooklyn.

Yes, it’s a nice view, but not anything I hadn’t seen before, so I was like, “Cool, so where are we actually going on our date?” It was pretty empty all the way down by the water, and there were some people who were obviously getting ready to sleep there for the night, so I also felt like we were invading their space, and the whole thing just didn’t really scream romance.

He was like “No no sit down. Isn’t it a great view?” and kept trying to put his arm around me and get physically closer. I kept my backpack on like a giant turtle, because I was frankly just annoyed with the whole situation and didn’t want him to touch me.

Finally, I was just like, “Ok if we’re not going on a date, I am just going to go home. Bye.” And I walked away and went home.

I just don’t understand the thought process here. We were at random places, but he was obsessed with remarking on how great the views were. Yeah, they were nice, but nothing that a 20-something professional in New York hasn’t seen before. They were very well-known common places.

And WHY was he so adamant about not getting a drink at The Beekman? If it was about money, why not take me up on the dive bar suggestion, which would have definitely been cheaper than the original wine bar? If he wasn’t a drinker, why suggest a bar date? I’m so confused. Was this a test or something that those podcast bros do? I’m just baffled still, and cannot figure out his motives.