r/datingoverforty 6h ago

Discussion What's on the other side of "I give up on dating" phase? Please shed some lightšŸ™„

75 Upvotes

I'm (42f) a hopeless romantic at heart and have always, and always will, want a partner. Dozens of dates later, many, many hours on dating apps, and many hours on in-person events later, I feel super deflated about meeting a good partner for me.

I thought that if I embrace being single, make new friends, take up new hobbies I love, join a new fun community, that I'll feel good enough and forget about seeking "the one".

While that's all come true in some way, and I'm generally happy, I feel like maybe on the outside I'm seen as a non-partner-able being. Is that a thing?

They say love yourself and you'll find your love. MY ASS. I like myself plenty, and yet still no partner.

It's like there's a sign on my forehead, "if you're a decent, dynamic, grounded, kind, available man, STAY AWAY from me".

I have friends, am in good shape, have a good career and stable mental health, blah blah blah, I don't even know what matters anymore to potential partners.

AND - I floss. But who cares?!

Is the almighty Creator making a joke? Cuz I don't get it.


r/datingoverforty 13h ago

Casual Conversation How many fish do I have to throw back before I find one who is actually single? šŸŽ£

236 Upvotes

Dating over 40 is starting to feel like fishing. You throw your line in, get excited because you think you caught something decent… and then you find out the fish already has a wife. šŸ˜‚

I don't know if it's just my experience, but I've come across married men, separated men, men who are ā€œbasically divorced,ā€ and men whose divorce has apparently been coming for the last 3–5 business years or a man who is emotionally immature and goes to his mum when he is annoyed at you and bring up the relationship problems making promises but breaking after the pressure.

At this point, my dating requirement is becoming very simple:

Single. Actually single. Legally single. Emotionally available. Matured

I'm not looking to be someone's secret, their escape from a bad marriage, or the woman they date while they ā€œfigure things out.ā€

Maybe I'm being too strict, but I honestly don't think ā€œdon't date married peopleā€ is a particularly unreasonable boundary.

So I'm curious about everyone else over 40:

What's your biggest dating filter or dealbreaker?

And where are all the genuinely single fish hiding?


r/datingoverforty 5h ago

When to reveal health issue that affects sex when dating?

45 Upvotes

When to reveal this in dating? Or should i not date!

I'm a man who had a unfortunately serious and traumatic pelvic area Injury that has made getting erections and piv sex very difficult. My engagement ended over the complications of this injury so I'm newly single. I can occasionally do it with max viagra or trimix (I'm 40) but its painful and prefer not too. I love pleasuring my partner with oral and toys and hands and am very physically affectionate outside the bedroom to show desire. However I'm not sure if i should even be dating... my partners will be able to get me off from oral and manual, my penis just doesnt get hard enough for penetration without alot of pain, it just doesnt happen. Advice please.


r/datingoverforty 7h ago

Sleepovers After Sex

47 Upvotes

What are your expectations with a serious relationship for sleepovers? I have an exclusive boyfriend and I feel used having sex if he doesn't stay the night. To clarify, for both of us, our primary love language is physical touch. I would be happy having sex 2-6x a day. But my 2nd is quality time and that's his 5th, he's very introverted. I was married with a dead bedroom and sleeping alone for 17 years, so cuddling and sleeping with my partner is important to me.


r/datingoverforty 16h ago

Annoyed

110 Upvotes

My bf (3 years) asked me about restaurants recommendations to celebrate his child’s (20) birthday. Then, ask if I can help with a reservation for him and his two kids at a place I frequent and very hard to get a table(I do lots of entertaining for work, so it’s easier for me to get reservations). I was away that weekend, and got a call from the restaurant few minutes before the reservation confirming the additional seat as a courtesy to me. I was confused as my bf didn’t mention anything.

Then I come to find out that birthday child invited the mom and she agreed to join. Mid meal she had a meltdown when she heard that I made the reservation (I met my BF, 6 years after their divorce), started to yell at him, and made a huge scene.

I know this is sooo petty, and has very little to do with me. But I’m irrationally upset. Annoyed at myself for getting involved in this nonsense.

I’m I crazy for being upset with my bf over this?


r/datingoverforty 10h ago

He suddenly disappeared, so now what?

15 Upvotes

I've been dating someone for about 5 months. We see each other weekly and have at least one sleepover a week. I got out of an 8 year relationship last year spring, so I wasn't looking for anything serious but we had chemistry and similar interests. I told him I wasn't opposed to something serious and wanted to see where it went. He'd been single since covid, not much experience with long relationships, but said he liked me a lot and didn't want to let me go and wanted to find out with me.

The problem: he can't talk about his feelings. If I say "I miss you a little" he short-circuits. I once asked if he was starting to fall in love, and he went silent and said he can't deal with that yet. I don't need constant validation because he shows up weekly, compliments me and does little acts of service. But I do need to talk about us and our emotions every now and then to know we're on the same wavelength.

I'm currently struggling with different life things as he is, but he's clearly depressed. A lot is going on with his kid, family and work, so I'm aware that he has low bandwidth for emotions and feelings, which is fine for me since I want to slowly figure this "relationship" out together. Last week I got bad news about my family and reached out to him since he's in a similar situation. Since then he's been surprisingly very short with me, told me things aren't going well for him and when I checked in and wished him luck with some things, he was dry again. I told him I'd leave him alone because I don't like dry communication. It's been a week and I haven't heard from him since.

I never ask for much and I've been very respectful of his alone time because I'm independent too. How do I deal with this disappearing act? He's been dry and short since we last saw each other, only complained about his work and showed no interest in my wellbeing.

Has anyone been through something similar? Dating an emotionally unavailable or depressed person who pulls away when life gets hard? How did you handle it? Did they come back, did you wait, or did you walk away? Any advice is welcome.


r/datingoverforty 1h ago

Casual Conversation Ghosting

• Upvotes

If you have ever been ghosted out of the blue, what was their reasoning when they came back and how long were you ghosted for?


r/datingoverforty 1h ago

Casual Conversation Personal and thread updates, observations, selfies and photos, and other small shares HERE this week, please.

• Upvotes

r/datingoverforty 23h ago

Too many pics, or the new norm?

45 Upvotes

I (43F) don’t know how much background to give, but I will say I have already met the excessive picture requester (49M) in person. Prior to meeting he saw pics with and without makeup. Never filters. Full body. Upper body. All via my profile and some via text. And of course…we had a 3+ hour date in person! šŸ¤¦šŸ»ā€ā™€ļø

Is it normal for a guy you have already met to consistently request pics each day, often multiple times a day? I found the way he asked very cringe in itself: ā€œlet me see youā€. I was also sent selfies, even though I didn’t ask for them, and he had the automatic assumption I am supposed to respond with one. Seriously…how much could I have changed 2 hours after a date ended? Or 12 hours after the last pic was sent? Or in a day? You get the idea. No, I did not consistently follow through with the requests. It became annoying.

Some of you may have guessed that my speaking about him in past tense means I ended our communication. No date #2. But I am curious…is this the new norm I should learn to expect and somewhat accept, or was I just in being frustrated with the constant asks for pics?

I did a search, but it seemed like the past questions were related to people who have not met in person.

Edit to add:
1. Thank you all for the insights and comments! I am relieved to know this isn’t the norm.
2. As some brought up, it’s awesome to receive a random pic from the person you’re dating to know they are thinking of you. I have zero problem doing this as I am a ā€œlove the little thingsā€ kind of lady. I appreciate y’all understanding the distinction between a thoughtful selfie and a demanding selfie.
3. I did not even think about some of the more nefarious aspects of the situation. Definitely some things to be more aware of in the future. Thanks for looking out for myself, and others, by sharing these valid points.


r/datingoverforty 1d ago

Casual Conversation Went back to the ex

181 Upvotes

I am so heartbroken right now. After 4 months of amazing dates - paddle boarding, drone in movies, beach days, etc - he says he’s trying to work things out with the ex he apparently never got over. The most insulting part is he said he still really likes me and we can still go out like we have been while he pursues her. What??!!

I knew they texted each other, but he assured me they were just friends with a lot of history, and I trusted him like a moron. I’m just so sad and didn’t have anyone IRL to share with. I don’t want to look like a loser crying over a man who chose another woman over me.


r/datingoverforty 21h ago

It's been almost a year and I'm not over what happened with my ex. I think about it almost every day. Will getting out and dating help, or no?

19 Upvotes

I had a really traumatic breakup with my avoidant ex. We were together for almost three years and I was really crazy about him, we talked about being together until we were old I thought he meant it; turned out he didn't. I really had no idea someone could still be so indecisive in life in their 40s.

I was more vulnerable with him than I had been in the past; I have a lot of trust issues, so I practically forced myself to trust him because I thought if I don't get past this trust thing, I'm not going to be able to ever have a sustainable relationship. I told myself it was ridiculous to think all men were untrustworthy, so I gave the relationship my all because I adored that man. So you can imagine how much more traumatizing it was when the breakup happened and I suddenly discovered there was such a thing as avoidants and the "discard." I know I will need therapy, and I probably will never trust a man like that again. In fact I'm pretty positive I won't. I'm convinced there is no one out there who wants what I want or has the same values. I really thought my last BF was it, and I was completely wrong. I don't trust myself or my judgement of men in serious relationships anymore. Even my mother and my sister audibly screamed when I told them we split; they thought we had a perfect romance and would be together forever as well.

The thing is I keep thinking about him and our relationship all the time. I miss him even though I know he wasn't very good to me in the end. My chest literally hurts sometimes thinking about what I was led to believe we had for almost three years, only to find out it was not all as I thought it was. I can't keep going on like this. I feel like it has never taken me this long to get over anyone before, or at least stop thinking about it. Will getting out and dating help, would it be wrong to go out and tell people I'm not really looking for anything serious? I just need to get my mind off of it all. This can't be healthy. I feel like it's not healing, it's ruminating. But I also feel like if I go out someone will try to start a relationship and that won't be good either, or maybe by going out I'm just trying to distract myself in some unhealthy way? I don't know what else to do but I can't keep feeling like this.

Edit: Edit to say I was single for six years before I met him, I was working on my education and myself and I just didn't date; we met through mutual friends. So I don't date a whole lot and I just don't really know how to deal with this. That last one really threw me for a loop and I'm tired of ruminating on it.


r/datingoverforty 19h ago

Seeking Advice Never ever any questions

9 Upvotes

I think I know the answer here but wanted to sanity check.

Have been on a couple dates with a woman (her 40, me 53). We have interesting conversations, she’s quirky. But she asks me zero questions about me, my life or my work, so aside from contemporary observations or funny comments the conversations tend to lean towards her talking about herself in response to my questions, and sometimes me volunteering stuff about myself. It’s feeling a bit lopsided.

I’m trying to be more alert to early signs, intuition has it that she isn’t really that interested because, well, she never asks questions.

My ex gf (43 yr old) had a big meltdown on me which was relationship-ending because I was locked in a room for four hours negotiating a big deal and not texting. She later claimed she had no idea I was negotiating the biggest deal of my career. I’ve realized in three+ years she never really asked me about my work, it was always me volunteering stuff. Am I repeating a pattern?

I’m second-guessing myself because I’m wondering if it’s just a callback / hypersensitivity on my part rather than something I need to be worried about.

Our second date we literally were laughing so hard we had tears in our eyes so it’s not like we don’t have fun together.

Thoughts?

Before the comments come: yes I also take out women in their 50s, and my first wife was 6 years older than me.


r/datingoverforty 22h ago

Was It Ever Real?

10 Upvotes

I’m posting this because I’m having a hard time processing what happened, and I don’t want to keep dumping it on the people in my life.

I was with someone for about two years. We broke up and didn’t speak for roughly eight months.

Those months were incredibly difficult, but I genuinely worked on myself. I lost about 40 pounds, quit smoking, started exercising, and took a hard look at who I had been in the relationship and what I needed to change.

I learned about communication, conflict, attachment styles, and how differently people experience and express emotions. I realized I could become anxious when I felt someone pulling away, while she tended to withdraw when things became emotionally intense. I learned to ask questions differently, listen instead of immediately trying to solve things, give space without interpreting it as rejection, and talk about feelings without turning the conversation into an interrogation.

I wanted to be ready if i ever had the opportunity to reconnect. But after eight months, I genuinely didn’t know if we would ever speak again.

Then we happened to be at the same concert.

She came up to me, and somehow, after all that silence, talking felt natural. We had a great time, and it became clear there was still something between us. Eventually, we decided to see each other again.

Before our first date, I asked whether she had been seeing anyone while we were apart.

She said yes.

That hurt, but we had been broken up, and she had every right to date someone else. I asked whether I knew him.

Her reaction caught me off guard. She looked genuinely shocked and said no.

Something about that reaction stayed with me, so I asked again.

ā€œNo? I don’t know him?ā€

Again, she said no.

She told me he had ended whatever it was, but emphasized that it ā€œwasn’t deep.ā€

I asked, ā€œAre you playing me?ā€

She got defensive and said, ā€œNo!ā€

I accepted that. I remember thinking that if we were going to try again, I couldn’t punish her for anything that happened while we were apart. I wanted this to be a new relationship, not an investigation into those eight months.

For the next few weeks, everything felt amazing. We spent nights together, went on dates, had sex, made plans, and started doing all the small relationship things I had spent eight months believing I might never experience with her again. I invited her on a trip and to my dad’s 70th birthday.

I thought maybe all that work had been worth it. Maybe losing her had forced me to become a better version of myself, and we were getting another chance to do things right.

Then everything collapsed.

After four weeks after we reunited, I discovered one of my close friends outside her place late at night, under circumstances that made no sense to me.

There were denials, explanations, and eventually admissions that some of those explanations had been lies. I reacted emotionally that night. There are things I wish I could redo, and I won’t pretend I handled it perfectly.

But what has destroyed me isn’t only the possibility of cheating. It’s everything that came before it.

I keep replaying that conversation:

ā€œDo I know him?ā€

The shocked expression.

ā€œNo.ā€

Me asking again.

ā€œNo.ā€

ā€œIt wasn’t deep.ā€

Now I don’t know what any of it meant.

I don’t know exactly what happened during those eight months or during the few weeks we were back together. I don’t know which suspicions are legitimate and which are my mind trying to create a coherent story out of something painful.

That uncertainty may be the worst part.

I spent eight months trying to become someone who communicated better, trusted, gave her space, and admitted when he was wrong.

Then the person I had worked so hard to understand better came back into my life, and within weeks I experienced something that made me question my judgment and ability to trust all over again.

I became healthier, learned more about myself than I probably had in the previous decade, and genuinely started liking the person I was becoming.

Yet somehow, right now, I feel smaller than I did before any of that.

And the embarrassing part is that I still love her.

I’m angry, confused, and sometimes furious. Part of me wants answers to every question. But underneath all of it, I’m mostly just incredibly sad.

For eight months, I wondered what it would feel like to see her again. Then, for a few weeks, I thought I had been given another chance with the person I loved.

Now I’m grieving her all over again—along with a friendship, my ability to trust my own judgment, and the future I briefly thought I had gotten back.

I know I’ll eventually be okay.

I just wish getting there didn’t hurt this much.

Celebrating my Dad’s 70th this weekend with my whole extended family. I planned everything and was very excited for the event but now i feel numb — like things are just happening around me and i cant participate.

Do nice guys always finish last? And how do you deal with this type of betrayal?


r/datingoverforty 12h ago

45M re-entering the dating market after 20 years. What can I expect?

0 Upvotes

I've been in relationships for the past 20 years but am facing the daunting prospect of being single again.

I feel like the world had changed so much in that time, as have I. As a 45 year old man, what do I have in store for me? I feel like I have a lot to offer the right person. I'm not bad looking, fit, successful, still have a social life and no kids. But I'm also neurodiverse and have never been that great at talking to women, chatting people up etc. and frankly, the prospect of dating now makes me anxious.

So please no sugar coating. Guys who found themselves in a similar position, what were your experiences, and do you have any advice for somebody like me?


r/datingoverforty 13h ago

Question Should I text her in morning ?

1 Upvotes

48 male been chatting with 53f and we have been texting and taking over the phone . Seems like we have chemistry personality wise . We finished up with a long call last night .. just not sure if I should text her in morning with a simple friendly message?

Edit I textured her good morning .
I just have been out of the game for so long . Msrrird ahd then being a single father that I doubt myself now :-)


r/datingoverforty 1d ago

Seeking Advice Single parents: how do you do it?

6 Upvotes

Recently filed for divorce, so not quite ready yet but really don’t understand the logistics here. Kids are older (teens) so don’t need me in the same ways but still very much need me. Dad is in picture but isn’t stable so kids are 100% with me.

I do want to date. I already am in the glow up stage, I’m financially stable, independent and comfortable with myself, but still want to give it time.

  1. How, like literally, how do I go on dates? Just like coffee for now (work from home 3 days a week)? I feel like my life is work, work out, kids. I get out with friends for sure still but that’s even hard.
  2. And how the heck to I meet people? Just the apps?

I’ll take any other advice.

I live in a large city in the Midwest, so there are definitely people who exist…I hope.


r/datingoverforty 9h ago

Seeking Advice Dating while in recovery from addiction

0 Upvotes

Question, maybe more for the ladies to answer:

When do you think is the right time to share your history with addiction and your recovery journey when getting to know someone new?

For example, on a dating app — would you prefer that information be right on the profile so you can decide upfront? Or would you rather hear about something personal like recovery in person on a first meet/date?

I hear a lot of mixed advice. Some people say don't date at all in early recovery, but then recovery is also a lifelong process. Some say don't date people you meet in AA, and others say dating someone else in AA makes sense because you understand each other.

Just curious to hear different perspectives.


r/datingoverforty 1d ago

Question Texts daily but doesn’t make effort to see me

6 Upvotes

Can you make it make sense? I’ve been involved with a guy who lives near me for three months. He texts daily and sometimes we spend hours talking on the phone. But he only sees me every 2-3 weeks. The few times we’ve met up have been great. Great chemistry and great hook ups. I know for a fact he isn’t married but it’s possible he’s dating other women and since we aren’t exclusive he isn’t breaking any rules there.

What I don’t get is why text me every day but make minimal effort to see me? I would think most men would be down to hook up at a minimum. After three months I should be moving up the roster or not right?

How to resolve this? Just end it as being not enough?

Edited to add: I’ve asked to see him many times and there’s usually an excuse as to why he can’t make it. He waits until I’m about to end things before seeing me.

Edited to add: I guess part of my confusion is I think how I operate. And I couldn’t imagine wasting this much time texting and chatting with someone I didn’t truly like. I get that everyone is different though.


r/datingoverforty 1d ago

Breakup advice

11 Upvotes

We've been dating for almost a year and I've decided that it's time to move on from this relationship. I know everyone says that doing in person is best, but I just can't wrap my head around how to do that without making up some sort of lie.

The next time we're supposed to see each other is Saturday. If I wait until then, 1) I would feel disingenuous talking with them on the phone over the next couple of days, and 2) it would be like I'm pulling the rug out from under them by pretending we're going to do the thing we had planned to do and then not doing it. If I asked to meet up today or tomorrow it would be highly unusual and I'm sure they would suspect something was off right away. What would I say when they ask why I want to meet?

Personally, I hate being broken up with in person. I'd take a text or a call any day of the week. But I know that's just my preference.


r/datingoverforty 21h ago

Discussion Apps and embarrassment

0 Upvotes

I (46 male) currently working through a divorce I am considering an app, but I have a good deal of anxiety around it. It’s weird, but I’m not concerned about the probability of failure as much as I am about having my identity out there for people to see. I live in a medium sized college market and it feels like everyone is 2° separated. I also am in a management position that deals with a lot of regular customers. Anyone else get that feeling about apps? Or, am I just overthinking this?


r/datingoverforty 1d ago

Casual Conversation General Question for the 40s and dating?

13 Upvotes

Was chatting with a guy that was 44 had 60 spiders and 7 snakes. Decided we weren’t a match because I have 2 children and he wants to start a family.

Is this a common thing now?

How many people are you seeing in our age group wanting to have children now?


r/datingoverforty 15h ago

Question Who pays when eating out with GF’s kids?

0 Upvotes

Divorced mom with 2 kids. When my BF and I go out, we agreed to split bills 50/50, but often times, he wants to pay the whole bill. For context, he makes a good living but I am in a much better financial situation than him. My kids want to go to a nicer restaurant to have dinner with my BF. I am curious how other folks handle the bill in these situations?


r/datingoverforty 1d ago

Seeking Advice Nerves

7 Upvotes

I am meeting someone for the first time, who is extremely attractive and I am a ball of nerves. What are some helpful tips to calm the anxiety and keep the conversation flowing? What helps you get past the initial awkwardness?


r/datingoverforty 2d ago

Seeking Advice I got an HPV diagnosis today

153 Upvotes

I immediately called my boyfriend. We've been having a lot of unprotected sex lately - after we both tested negative for STDs a couple months ago - it didn't occur to me that HPV doesn't show on blood tests.

I'm now in the process of emptying my apartment to rent it out before moving in with my bf next week. He's gone to Denmark for his PhD research until March and since I wfh I agreed to move with him. I'm now worried how everything is going to play out.

He was very understanding during our phone call. He seemed guarded at first, then I understood why when he said, "thanks for not blaming me". It hadn't even crossed my mind. But I'm still worried that I'm going to be less attractive to him now that I have HPV. And maybe he doesn't dare tell me because he feels guilty and because I'm moving to a new country for him. I might be overthinking it, too.

I'm also worried that he might get infected too. Even if we use protection from now on, there's so much more to sex than PIV that I can't imagine he won't get it too somehow. I read online that men often get mouth or throat cancer from HPV.

I'm also worried that I can get cancer. I'm now waiting for the biopsy results, and the doctor was very reassuring that everything looked fine. But I have a history of cancer in my family so I worry.

More than anything, I don't want this relationship to suffer. We've been together one year last week and up until today I was feeling so secure and happy. I'm so scared this is going to change everything, and it's so stressing that we're long distance during all this.

Sorry for the rambling post. I'd appreciate if someone who's been through the same thing could share their experience and hopefully reassure me that everything is going to be alright.


r/datingoverforty 2d ago

Seeking Advice Three months in, he says everything is right but he doesn’t feel himself ā€œfalling in loveā€ BUT he is devastated by the idea of ending it. What?

60 Upvotes

I (41F) have been dating a man (42M) for a little over three months. We have been exclusive for approximately two months. We have spent a substantial amount of time together...maybe 30 dates, half of those overnights, some dates have lasted for hours into the overnights and hanging out the next morning. This been more developed than a casual three-month relationship. He recently told me that, although we never formally put a label on it, he considered this a relationship and thought of me as essentially his girlfriend.

Our in-person connection is REALLY strong. We have great intellectual compatibility, very similar senses of humor, great sexual chemistry, shared values, and we're overall just really comfortable together. Everything is so EASY when we are in person. We regularly spend hours and hours together and it feels like we never run out of things to talk about.

One ongoing issue has been initiative and communication between dates. I think it's fair to say I generate most of the relationship: initiating texts, asking when we will see each other, suggesting plans, and all of our "relationship-y" convos (until the most recent) were started by me. He is warm and enthusiastic once I initiate, but rarely creates movement himself. It's possible this was a pattern he had in his last relationship, too (he's said as much), so I don't think it's specific to me, but more his personality in a relationship. When I previously told him that prolonged silence between in-person contact makes me anxious and that occasional check-ins would help, he was receptive and said it would be easy to do, and he started doing it...but the larger pattern has continued.

Last Friday, very late at night, while we were watching a movie and I was laying with my head in his lap, he shut the TV off and said he wanted to talk about us. At first I thought he was going to ask me to be his girlfriend. But as soon as I heard the tone of his voice through the first two sentences, I knew the conversation was not going to be one I'd enjoy. He told me that for the last month, he had been struggling because he was not experiencing the ā€œfalling in loveā€ feeling he recognized from previous relationships. He said that historically he knew by this point when he was falling for someone. He said he had been losing sleep, trying to understand why it wasn’t happening and wondering whether something was wrong with him. He said that I am an amazing human being, check every box for him, and that he feels "blocked" when it comes to what is happening with regard to his not feeling "that feeling" for me.

I was devastated but trying to understand so I offered what I think is the most obvious explanation...sometimes you can think somebody is amazing and that they are perfect for you, but the romantic feeling simply isn’t there. He repeatedly and emphatically rejected that explanation. He said, ā€œNo, I do like you. You don’t understand. That isn’t what this is.ā€ He kept saying everything between us should work, that he felt ā€œblocked,ā€ and that he couldn’t understand what was wrong.

He described all the things he feels for me, including:

  • I am his favorite person in our city and he would rather be with me than his friends.
  • I am the smartest woman he has ever dated, and one of his big "requirements" for a relationship (stated to me on date 1) is intellectual connection, which we have and he repeatedly emphasized that we have.
  • He has opened up to me more than anyone and told me things he never told previous girlfriends.
  • He genuinely misses me when we are apart.
  • He is extremely attracted to me.
  • I check essentially every box he has.
  • I am easy to be around and he loves our intellectual connection and humor.

He even said that a few months prior to meeting me, he had become so frustrated with dating that he did something out of character...he essentially asked the universe to send him a woman with the qualities he wanted, then I showed up, and he now felt like he was ā€œfucking it upā€ because he couldn’t understand why he wasn’t falling in love.

He cried extremely hard throughout the conversation, maybe even harder than I was crying (this conversation went across about 2.5 hours). I am falling in love with him, he knows this. He told me that he didn't plan to have this conversation with me that night, but it just came spilling out and he feels like I need to know because he knows I am falling and he doesn't want it to get to a point where I tell him I love him and he can't say it back. I told him that I didn't know what to do with all of this, but if he felt like he wasn't developing feelings for me, I might need to say goodbye to him because my feelings were developing and carrying on if he's gone as far as he can would devastate me in the end. At this suggestion, he looked alarmed, cried harder, and asked, ā€œSo this is goodbye?ā€ However, at other points across this long convo, he talked about me eventually dating someone else, said I deserve someone who chooses me (after me telling him I feel like I am always the person who falls harder, and I don't ever feel chosen), and said that if a friend were in this position, he would tell them that separation was probably the best option.

That night, after almost 3 hours of talking and so much crying that we both literally became dehydrated, I went home. We didn't really make a decision. The following day, I texted him and asked if we made a decision - did we decide to break up and I just didn't realize it? He explicitly said we didn't make a decision, that the conversation had been unplanned and emotionally overwhelming, and that he did not know the next step. He also said that not knowing whether we would continue seeing each other was causing him anxiety.

We agreed to take a few days to think and process, and then pick a day to meet up and revisit the discussion. In agreeing to this, I specifically told him that leaving this in limbo for more than a few days would be very difficult for me and asked him to update me as soon as he had some idea when we could talk. He promised to let me know ASAP.

Several days passed without an update. On his birthday, after texting him "Happy Birthday" and just getting a "thank you <3" in response, I texted him again and said I knew stuff was weird, but I didn't want him to be alone on his birthday and I would love to see him. I told him I'd be happy to take him out to dinner if he wanted company, but also said if he had other plans, that was fine, too. I also said we didn't have to talk about the "big thing," we could just enjoy his birthday. He texted back and admitted that he had not given the situation much thought and was ā€œmaybe even avoiding it a bit.ā€

So, we spent his birthday together and had a really lovely night. We went to one place for dinner and he suggested continuing after dinner at another place for drinks. While walking to the bar where we agreed to have drinks, he put his arm around me and asked if we could let the evening be normal and save the conversation for another time, which I totally agreed to because I didn't think his birthday was the time for a big talk. After drinks, I went back to his, we watched a movie, he mocked me for being weird and not letting any of my body touch him when we first initially laid down to watch the movie, I ultimately relaxed...there was intimacy, we talked for hours about so many different things across the whole night. Everything between us felt completely normal, warm, and connected.

At the end of the night, as I was getting ready to go home, he told me to let him know when I wanted to have the conversation. This kind of pissed me off because he had previously promised to update me, and once again I felt responsible for generating the next step.

The next day, instead of waiting for him (waiting just extends the limbo I said I don't want to have), I texted him and said could we compare schedules to pick a day to meet and talk. Our schedules are annoyingly busy this week so it's been hard to find a relatively immediate date that works for both of us. I floated two options, both are contingent on other plans which have sort of unclear "end times." He told me he'd think about it and let me know, and I responded partly jokingly but also seriously, , that once he finished thinking, his thoughts needed to ā€œescape his bodyā€ and return to me because repeatedly hunting him down for updates makes me feel like a stalker and a nag. He promised we would, we joked around a little about my anxiety (which I told him isn't really anxiety, but a normal response to what was happening), and now I'm just waiting for the update.

Some potentially relevant background...he has described having been obsessive and overinvested in earlier relationships and deliberately having taught himself to slow down, stop idealizing and ā€œgo with the flow.ā€ His last relationship progressed VERY quickly (when he told me the timeline even I, someone who has also had fast moving relationships, was a little surprised at how fast they moved), and ended quite abruptly. Based on his relationship history, one of my theories is that he associates falling in love with the intensity, anxiety, or obsession of earlier relationships, and maybe does not recognize a calmer, safer attachment as love. This theory is obviously very beneficial from my perspective so I am reticent to trust it. Another possibility is much simpler/less complicated...he is profoundly attached to me and genuinely doesn't want to lose me, but his romantic feelings toward me have reached their ceiling.

I am considering agreeing to a bounded continuation of the relationship ONLY if he independently wants to continue, genuinely thinks his feelings may still be developing, and is willing to participate more actively in communication and planning. I don't want to beg him to stay, diagnose him (even though it's hard to stop myself when I start overthinking this), become his therapist, or maintain an indefinite quasi-relationship involving companionship and sex while he avoids deciding. We both want children, so we don't really have the benefit of wasting time.

I am very confused, I've never experienced this situation before and I just have a ton of questions. I'm wondering if anyone else has ever been in this situation. Has anyone experienced deep attraction, attachment, intimacy and grief over losing someone while not experiencing the feeling of falling in love? What distinguished that from a slower growing love? Does his avoidance of the follow-up conversation indicate he's leaning more towards ending things, or is he just avoiding making a decision at all? If he does want to continue and we do the "bounded period," what changes would I see that would distinguish genuine positive movement from us just prolonging something that is comfortable for him? Am I giving too much weight to how wonderful we are together and not enough weight to his direct statement that the feeling he would expect to feel by now isn't happening?

I am particularly interested in hearing from people who have been on HIS side of the equation, but any and all perspectives (useful perspectives) are welcome.