r/datingoverthirty

This is the place to put shower thoughts, your vents/rants about dating, requests for quick advice, serious (and sometimes not) questions and anything else that might not warrant a post of its own.

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I am really struggling to make sense of what happened with a guy friend, and whether I ultimately handled things in a way that ruined not only the romantic aspect, but also the friendship, which meant a lot to me, so I can avoid repeating this situation in the future. 

So, about two years ago, I went on a handful of dates with a guy. Things didn’t work out romantically, but we got on really well and became platonic friends, something that I initially was completely fine with. 

About a year into the friendship, last summer, his behaviour started shifting from purely platonic. He’d pay for outings though I offered, flirt, initiated more physical touch, texted after every hangout to tell me what a wonderful time he had, offered to help me with mundane tasks, etc. As this behaviour continued, I slowly developed feelings for him again. I didn’t say anything for months because I didn’t want to be presumptuous and, irrespective of my feelings, I really valued our friendship and feared losing it.

Eventually, though, the dynamic became too confusing, so a few months ago, earlier this year, I brought it all up. He apologised for his behaviour and admitted that he’d had feelings for me too again at some point, but felt remaining friends was the right choice for him. He said he understood if I needed distance, but hoped we could stay friends and reconnect whenever I was ready because he really valued me. I accepted his decision, thanked him for being honest, but didn’t respond about staying friends because I needed some distance. 

After that neither of us reached out until I wished him a happy birthday a few weeks ago. I genuinely missed our friendship and thought enough time had passed that we could reconnect as friends. He seemed really happy to hear from me initially and engaged normally in the conversation. Then, after a few messages, he stopped responding. I’m now struggling to reconcile the fact that he was the one who said he hoped we could reconnect as friends, only to eventually fade. I know you can’t force a friendship, though…

In any case, I’d really value some perspectives on whether I handled all this badly, like whether me bringing everything up caused this outcome, and how his behaviour played a role in this too. Was this simply an emotionally complicated situation that I couldn’t have handled much differently, even if I’d spoken up sooner? 

This is the place to put shower thoughts, your vents/rants about dating, requests for quick advice, serious (and sometimes not) questions and anything else that might not warrant a post of its own.

This post will be moderated, so if you see something breaking the rules, please report it.

This is the place to put shower thoughts, your vents/rants about dating, requests for quick advice, serious (and sometimes not) questions and anything else that might not warrant a post of its own.

This post will be moderated, so if you see something breaking the rules, please report it.

A few months ago I posted asking for advice when someone (37f) broke things off with me (35m) after 3 months, without any prior red flags. Her reasoning was that the chemistry wasn't going to work for her - got some good advice and just pretty much tried to move on.

Anyhoo, there's a bit more to the story now, which I'm trying to get my head around.

3/4 months passed, and I just decided to reach out to her. Everything was civil, we just asked how we were, what we've been up to, and I just decided to ask her out for a drink. She said it was unexpected, but wouldn't want to meet as friends as she didn't want to blur any lines, so I explained I was asking her out as a date - she said ok.

We met up, everything felt normal, natural, no awkwardness, it was like we never broke up. It was just really nice to catch up.

Eventually we started talking about the relationship - she mentioned she's never been in something long term, and after years of bad relationships, the relationship between me and her felt jarring, something that she wasn't used to. She always stated how safe and calm she felt around me. I agreed, I felt the same way around here. We had the same values, no boundaries were crossed, and we always had a good time together. Nothing was mentioned about the chemistry issue.

She even said she dated someone for a couple of weeks after me, and their values didn't match up, and boundaries were crossed (he would still talk to ex-hookups while they were together), so she ended that. She mentioned she had done some unlearning/growth in terms of what she wanted, and basically noticed the pattern of what she would usually attract never working out, and that us ending was bitter sweet. She never reached out again to me as she thought I hated her (which I don't).

I explained my side, that I also felt very safe and calm around her, we both did small gestures, remembered the small things, consistent, making time for each other. And I just felt like it was a rarity from my side. There was obviously attraction there, she was very touchy feely when we met again. So we rekindled.

From what she was saying, and the fact that the chemistry issue from before wasn't bought up, it really felt like she alluding to that she was confused about the chemistry with me, and that it was unfamiliar, and it didn't feel like the chemistry that she used to have with previous partners (that never ended well) - anyone else see this? I personally see this as more of a common problem than people like to admit (just from various stories).

2 days later, we met again (she was keen to see me quite soon, and I was too). Everything again felt great, same conversations were had about the relationship, and it just felt good, there was hope!

2 days later, she texts, and ends the relationship again, now stating we have too similar disposition, and its not going to work for her. She may have just realised this, but the stark contrast from meeting up the first time and what she was telling me, to this, was just a bit baffling. I also don't think having similar dispositions is a bad thing - I feel like its a rarity sometimes, especially if everything else fits. I guess also, since she had this chemistry issue from before, what did she expect to change this time round as we're still the same people?!

I really do think deep down, she may still be feeling confused about it all, and what she actually wanted, because it always felt that it was this, but may have been scared of it. What do we think? Am I overthinking it? I also feel bad that she was almost there to understand something about herself and relationships, and that she's never had a good relationship, and she may just go through that vicious circle again (only she can learn this of course)

I guess I may have been a bit naive (words over actions etc)? And I definitely want to avoid this type of situation in the future - seems like a common problem for me in the last few years - they match my energy, they're always complimentary about my character and the relationships seems like what they're looking for, and then there's a sudden drop off out of no where.

I'll obviously take accountability for reaching out again, and putting myself in that situation, I just genuinely felt like something was there, and took the risk.

I am 34M, am going to go to couple of singles mixers in the city. The problem is I am a bit socially awkward and do not possess great conversational skill. I can maintain conversation. The thing is after like the basics - job, hobbies, interests, I don't know what else to talk about. I do see people talk continuously and often wonder, what do they talk about? What is it that makes women interested in talking with them like what holds it interesting.

This is the place to put shower thoughts, your vents/rants about dating, requests for quick advice, serious (and sometimes not) questions and anything else that might not warrant a post of its own.

This post will be moderated, so if you see something breaking the rules, please report it.

This is the place to put shower thoughts, your vents/rants about dating, requests for quick advice, serious (and sometimes not) questions and anything else that might not warrant a post of its own.

This post will be moderated, so if you see something breaking the rules, please report it.

This is the place to put shower thoughts, your vents/rants about dating, requests for quick advice, serious (and sometimes not) questions and anything else that might not warrant a post of its own.

This post will be moderated, so if you see something breaking the rules, please report it.

This is the place to put shower thoughts, your vents/rants about dating, requests for quick advice, serious (and sometimes not) questions and anything else that might not warrant a post of its own.

This post will be moderated, so if you see something breaking the rules, please report it.

This is the place to put shower thoughts, your vents/rants about dating, requests for quick advice, serious (and sometimes not) questions and anything else that might not warrant a post of its own.

This post will be moderated, so if you see something breaking the rules, please report it.

This is the place to put shower thoughts, your vents/rants about dating, requests for quick advice, serious (and sometimes not) questions and anything else that might not warrant a post of its own.

This post will be moderated, so if you see something breaking the rules, please report it.

This is the place to put shower thoughts, your vents/rants about dating, requests for quick advice, serious (and sometimes not) questions and anything else that might not warrant a post of its own.

This post will be moderated, so if you see something breaking the rules, please report it.

tl;dr finally processing one-sided breakup. I tend to be self-negative and think I need to protect people from myself, so I'm scared that I'm both going to start dating again too early, and that I could also just wait forever. I'm looking for some kind of benchmark for "healthy enough to date again".

*edit: I'm trying to figure out how to distinguish between "I need someone to fill the void left by my ex" (bad) and "I'm normal amounts of lonely/wanting a partner, and my ex is the only frame of reference I have for what it would feel like"*

My ex cut things off about 5 months ago after 2.5 years and talks of marriage. She wasn't the best at saying or even knowing what she wanted, and finally did in an ultimatum with a few days to figure my shit out. I actually did figure a lot of it out, and then she just cut things off hard. I tried reaching out once a few weeks ago and she's not interested in reconnecting.

I'm working on letting go but it's slow going. I had an awful last year and let that change me, and our last conversation was while I was coming off a really awful work trip with bad sleep. I've spent the last 5 months doing my damnedest to learn from that, for myself and my loved ones, but with a bit of hope that I could earn her trust/hope back. Obviously that's not going to be a thing and I'm focusing on trusting her judgement.

So now I'm working on acknowledging her part in things, rather than trying to hold the love, and figure out what I want apart from her.

She was very good to me and I need to integrate how she treated me (some of it) into how I treat myself and others. I hope some of how I treated her was helpful long-term.

But also I have a horde of pictures and gifts from this person I still want to respect, but that I assume I can't bring into a new relationship in a healthy way. I'm not sure how to respect those incredibly personal items while getting them out of my life. The best suggestion I've heard so far is "put them in a box and give them to someone you trust until you don't care anymore, especially if you had a kid together so they can see that stuff" (we didn't, but I thought I'd include it).

I'm kind of isolated and how I feel about dating again is generally "yeah let's go" when I've been with friends recently, and "oh no, I'm going to get rejected for not having my shit together/crying/oversharing" when I'm by myself for a bit.

I'm in a loop of downloading, peeking at, then uninstalling Hinge as some kind of hope-boost (not my best idea).

I'm finding people I'm interested in, but a lot want kids, which I'm down for, but with more time to figure my head out and get to know eachother first, and I feel like I'm running out of years for that.

I’ve been friends with a guy for a little over two years. We used to live in the same apartment complex like right next to each other, and I recently moved just a few buildings down same street. We live in a close-knit neighborhood, have mutual friends, and still run into each other regularly.

I’d had a small crush on him in the past but talked myself out of it because I valued the friendship and didn’t want to make things awkward. He’d always been genuinely kind to me, and after two years of friendship I trusted him quite a bit.

After he found out I was moving, he asked me out. We kissed, and he told me he’d wanted to kiss me for a long time but hadn’t because he didn’t want to make things weird while we were neighbors. After that he started inviting me to movies, neighborhood events, and little one-on-one hangouts. From my perspective, it felt like we were intentionally exploring whether there was something between us.

We ended up sleeping together a few times over about a month.

The morning after the last time, we were cuddling in bed when he said he wanted to be honest because he didn’t want to hurt me or give me the wrong impression. He told me he wasn’t looking for a relationship, was also seeing another woman (who he’d apparently told the same thing), and that he’s naturally very affectionate but didn’t want me interpreting that affection as romantic intent.

I appreciated the honesty and told him casual relationships aren’t really for me anymore.

A few days later he joked about setting me up with another guy I’d once mentioned was cute. Given what had just happened between us, it landed badly. I told him privately that it felt disrespectful, and he apologized immediately and then again later over text.

I eventually told him I wished the whole situation had been handled with more care because we’d been friends for years. He was receptive and told me to take whatever space I needed.

I’m not confused about whether he owed me a relationship—he didn’t. What I’m struggling to understand is the disconnect between the sweet, considerate friend I’d known for two years and how casually he seemed to approach sleeping with and pursuing me. It feels so cold.

If you’ve been on either side of something like this, how do you interpret that disconnect? Can pursuing a longtime friend this way genuinely feel completely casual to someone, or does this sound like poor communication/consideration on his part?

And for anyone who’s had this happen with someone who remains in your social orbit: how did you recalibrate the friendship afterward?

This is the place to put shower thoughts, your vents/rants about dating, requests for quick advice, serious (and sometimes not) questions and anything else that might not warrant a post of its own.

This post will be moderated, so if you see something breaking the rules, please report it.

This is the place to put shower thoughts, your vents/rants about dating, requests for quick advice, serious (and sometimes not) questions and anything else that might not warrant a post of its own.

This post will be moderated, so if you see something breaking the rules, please report it.

This is the place to put shower thoughts, your vents/rants about dating, requests for quick advice, serious (and sometimes not) questions and anything else that might not warrant a post of its own.

This post will be moderated, so if you see something breaking the rules, please report it.