The other night was something I never expected and it was almost like being transported back to when I was 22 and everything was new and exciting. A beautiful woman (39 years old) matched with me (36 M) on Hinge and we chatted for a bit. Initially she declined going out when I told her I have a young kid, but then just a few minutes later, she changed her mind and asked what I was up to that night.

Initially it was supposed to just be a standard date type of deal — we met at a local spot near me for a couple of drinks and just chatted. Then we ended up going to one more spot around the corner and kept going. She was messaging with a friend who was planning a big night out and asked if she could meet with them and bring a date. So the next thing I know, we’re in my car driving downtown around 10:30 or so to meet with some people I’ve never met.

Anyways, fast forward a bit, we’re at her friend’s place and then eventually everyone is corralled and then we head to this night club — which is not my scene at all. We’re waiting to get in and it’s just super tense because a couple of people in our group weren’t dressed according to code. At this point, my rational mind was telling me I needed to get out of there and that I couldn’t afford to screw up this project at work that’s been on my plate. Suddenly, her friends start going in and she asked me to stay for just one drink.

That “one drink” turned into us dancing and kissing and laughing for the next couple of hours. After the crazy weird club, her friends wanted to go to some other bar, and at this point, I’ve already decided that there’s just no way I’m going to be able to work the next day. Mind you, this is a Tuesday night. We get to the next place, I order her friends a drink, get her a drink and it just keeps going. Everyone is pretty wasted, but I somehow had my wits about me (enough) to get us back home afterwards.

We ended up staying over at my place (nothing bad happened) and then woke up the next day and decided to just make a day of it. I called in sick and my boss didn’t give me any grief, which was a relief. She suggested going to a farmers market and I mentioned the beach. We ended up laying in the bed for a while, listening to music, and just being present, then took my dog for a walk and got coffee. After that, we ended up heading out to the beach for a while. We talked about life and whatever we were experiencing — she was still pretty sad about the breakup she was going through.

Anyways, we both started finally feeling like crap and she asked for a ride home. At this point, it’s about midday the next day after our date night. We drive back to her place (which was a bit of a hike) and I dropped her off. As she was grabbing her things and after we kissed goodbye, she said “Well, see you around,” which seemed like a bad sign to me, but I tried not to read into it too much. She checked in with me a bit later to see if I made it home alright, and we kept messaging from there.

I tried to call her later in the evening to just check in and I guess talk about what a crazy experience everything was. She didn’t answer and said she was on the phone with a friend. Eventually, a couple of hours later, she texted me, “Can I be honest?” which I immediately knew was not a good sign. She said that she had a ton of fun and was glad I got to meet her friends, but she didn’t really feel a romantic connection but she wanted to stay in touch and have me in her life in some way. Obviously, that’s not what I wanted to hear — especially after calling in sick to work and more or less being irresponsible and dropping my obligations to spend time with her.

I called her and she answered and we just talked about the previous night and her takeaway. I told her I was attracted to her and was hoping to keep going out as romantic prospects and that I wasn’t sure if “being friends” was going to be easy or work for me. We really are different though, and I think we both sensed that almost immediately — she’s a downtown girl, grew up with privilege and dates wealthy, successful men, and I’m just like an aging hipster young dad. I was hoping to see her just one more time. Maybe we still will one day… All I know is that those 16 hours that we spent together was definitely a roller coaster and I imagine if I kept seeing her, it’d continue to be a crazy ride (good and bad) with a lot of unexpected twists and turns.

edit: After our call last night, she sent me a text saying “Now I feel super guilty and bad.” I didn’t respond right away, but I was definitely frustrated by it. You’re the one rejecting me but you feel bad and now I also have to manage your hurt feelings in addition to my own? That’s not fair. At first I thought maybe I just don’t say anything or not respond and see if she reaches out in a week or two. I had realized that she had hidden her Instagram stories from me when we first started following each other the other day, but she had unhidden it from me, which was also kind of another weird thing. Anyways, I did send her a message a bit ago effectively saying, “I don’t want you to feel bad but I’m the one being rejected here so I need to protect my peace and not be made responsible for managing yours.” She responded within like 10 seconds with, “I completely understand. Take care :)” and at that point, I realized that there was no interest in “friends” or staying in touch or whatever — it was like she just totally dropped the facade. It just seems so fake and selfish. Anyways, at that point, I unmatched from the dating app, removed her from my Instagram and blocked her number. Yeah, it’s a little extreme, but I’ve already been put through a lot of emotional ups and downs with this one over the last few days. I need to get off the ride and focus on moving myself forward. She also took one of my favorite shirts the other day and I guess now I’ll never get it back. FFS.

11 comments
  1. Damn, sorry it didn’t work out the way you wanted. I think you handled everything the best that you could by being up front with her and letting her know that you were interested more than just being friends. Good luck on your next date

  2. Best bet now is to just distance yourself and see if that attracts her back when you stop showing interest. Either way you probably can’t take her serious anymore

  3. I’ve been this girl.
    She was confused and hurt from her ex and maybe wanted a relationship/just wanted to try. I would say that she didn’t maliciously try to hurt you, they wasn’t her intention. Sounds like she was just really confused.

    Sorry mate. But keep working on yourself. Take the experience for gratitude!! You know you are attractive <3

  4. Just an update… I’ve also edited and added to the original post…

    After our call last night, she sent me a text saying “Now I feel super guilty and bad.” I didn’t respond right away, but I was definitely frustrated by it. You’re the one rejecting me but you feel bad and now I also have to manage your hurt feelings in addition to my own? That’s not fair. At first I thought maybe I just don’t say anything or not respond and see if she reaches out in a week or two. I had realized that she had hidden her Instagram stories from me when we first started following each other the other day, but she had unhidden it from me, which was also kind of another weird thing. Anyways, I did send her a message a bit ago effectively saying, “I don’t want you to feel bad but I’m the one being rejected here so I need to protect my peace and not be made responsible for also managing yours.” She responded within like 10 seconds with, “I completely understand. Take care :)” and at that point, I realized that there was no interest in “friends” or staying in touch or whatever — it was like she just totally dropped the facade. It just seems so fake and selfish. Anyways, at that point, I unmatched from the dating app, removed her from my Instagram and blocked her number. Yeah, it’s a little extreme, but I’ve already been put through a lot of emotional ups and downs with this one over the last few days. I need to get off the ride and focus on moving myself forward. She also took one of my favorite shirts the other day and I guess now I’ll never get it back. FFS.

  5. I was fine until I read that last sentence. Shit happens, but dude, get that shirt back. You didn’t do anything wrong and there’s no need to hold back.

  6. I’m confused. You said nothing bad happened at your place. Did you two not have sex?

    I don’t have all the facts here… but I think it was a bad move to meet up with her friends. You two are on a date, who cares what her friend is doing? The momentum you two built up getting to know each other one-on-one changed when you hung out with a group.

  7. I mean it sounds like from the beginning she wasn’t really interested in dating because of your child and was just looking for a hookup/possible fwb. Is it crappy she didn’t just communicate that? Absolutely. But you didn’t either. You just assumed she changed her mind and was fine to have a relationship.

    I can understand the frustration of thinking things went well and hoping for the future and then getting let down. That’s absolutely valid, and unfortunately happens a lot in dating. But I really think next time it would be best for you to talk about boundaries. Explain what you are looking for, make clear where you are at, and clarify where she is at and what she wants. This woman doesn’t seem to really be in a stable place emotionally and isn’t looking for longterm compatability and that’s a bummer.

  8. Yeah people suck and dating is hard. I think you handled it super well ! And even if it didn’t work out sounds like it was a fun night. Just keep meeting people but maybe next time go with your gut if you’re not feeling it’s your kind of thing

  9. I’m annoyed on your behalf about the shirt. I mean, she shouldn’t take your stuff with no intention of returning it, like a souvenir.

  10. It’s definitely annoying as hell to be rejected while simultaneously feeling expected to make her feel less bad about rejecting YOU. I feel that one. But I don’t think she’s expecting you to manage her feelings, just trying to sugarcoat the rejection in the best way she knows how – which isn’t a very good way – but there really isn’t a good way.

    If she doesn’t say she feels bad then it’s just a really cold rejection which would make you feel like shit too. It’s like she’s trying to sugarcoat the sting cause she actually does feel bad somewhat but she’s twisting the knife unintentionally.

    Then I think she sensed you being pissed at her and just took an exit with that “take care :)” cause once you go there (being pissed), it’s over with most women you just meet. I understand your frustration completely, but she also doesn’t have a great option for not looking like an asshole once she rejects you so that’s where I think that came from.

    At least you had fun that night, and if it were me I would’ve taken the chance and called in sick at work too cause you never know what it might turn into. Maybe next time will be with the girl who sticks around, y’know?

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