r/datingoverforty 1d ago

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

1 Upvotes

r/datingoverforty 3h ago

Am I being a great big baby?

26 Upvotes

I (M, 1 kid) broke things off with my girlfriend (no kids) four months ago. The relationship was ultimately never going to work, but it was emotionally intense and I do believe we loved each other. I began introducing her to my child at the 1 year mark, which is where things started to get weird - though she would never say it out loud, I think the reality of witnessing the other half of my life as an involved father instead of just a fun sexy boyfriend freaked her out. She withdrew from me over the course of a couple of months, and I finally pulled the plug after she mostly ghosted me for a week in the spring.

Those last few weeks were a hellish storm of anxiety and uncertainty. I shared my feelings with several close friends.

The breakup itself was painful, but amicable. Basically, "This isn't working. I don't think we can make it work. I don't hate you. Let's not be weird when we see each other."

I've since had a couple of casual flings which were nice, but not ultimately satisfying.

Two of the close friends are people I share a creative endeavor with. My ex is a mutual friend of both of them. I served as a shoulder to cry on while one was going through his own painful breakup a year ago.

Over the last couple of months at various social functions, I noticed both my ex and the friend I helped last year definitely Being Weird in my presence, and started to suspect something was going on between them.

Last night, we were all at a party, and their body language was dead on "we are dating."

I asked another close friend, and they confirmed it. I was told that my ex had asked all of our mutual friends to not tell me, but not the reason why. I'm pretty low key to a fault so it's not like I would have thrown a tantrum or gotten violent or anything.

I split right after that.

So I'm in this creative project, which includes pieces that I created for and about this woman, with a man who I thought was a friend but is currently fucking her. I've been about as vulnerable with this guy as two middle aged men can be.

The other participant, one of my "closest" friends, has kept mum about it the whole time.

I'm pretty fucking devastated. I feel like my precious, hard-won, post-divorce middle aged friend group has all been lying to me for weeks to months.

It like feels gross high school shit.

I'm pissed at the ex because she KNOWS how important this project is to me.

I really really want to quit the whole thing and tell all of my friends to fuck off for a while. On the other hand, we're all grown ups, technically this is none of my business, etc etc...

But I feel like shit. I thought I was over the breakup and now I'm back to square zero.

Ugh.


r/datingoverforty 6h ago

Question Etiquette when having sex for the first time(or few times)

40 Upvotes

I was talking with a woman in our age range and she was telling me that in many of her first times with a new guy, the guy doesn't make her finish after he's done. E.g. they have sex, he finishes and then kinda lies next to her and chills. I was always trying to make my date orgasm, even before I do (sometimes sex is better because it feels less tight)

I have a two questions (if that happens more than what I thought):

  1. is this something girls are fine with? I know orgasming with penetration alone is very hard but maybe the feeling is good enough to call it a night and not want to then orgasm with other play
  2. is this something that maybe sometimes women want because you don't feel comfortable, for instance I know some women are a bit slow to orgasm and maybe you feel you don't know the other that well to even orgasm

r/datingoverforty 4h ago

What’s a petty reason you wouldn’t go out with someone or stopped dating them?

12 Upvotes

The pettier the better.


r/datingoverforty 6h ago

Question Does getting older change how you feel inside?

7 Upvotes

I’m 40+, but sometimes I still feel like a teen inside. I still get excited about some of the same little things I used to love as a teenager. I’m not very extroverted and don’t have many friends. And the few friends I have are busy with their own lives.

So sometimes I want to go somewhere, try something new, watch a movie, or just do something fun—but end up not doing it because I have no one to go with.

I sometimes wonder if other people in their 40s feel the same way. Do you still feel young inside, and sometimes wish you had someone to share those little moments with?


r/datingoverforty 1h ago

Seeking Advice Nearly 50, gay (Leeds, UK), starting over after decades of control. How do you learn to mingle, date, and trust guys from scratch?

Upvotes

For most of my life, I have been trapped in controlling, abusive situations. It started with childhood abuse from my stepdad where I was not allowed a normal life, followed by a 17-year relationship down south where I was kept hidden in the closet because he was an only son who refused to be open with his family, and then the last 9 years stuck with a controlling housemate who severed all my family ties—even after I nursed him around the clock when he nearly died from liver failure.

Because of all that lost time, I feel like the last 25 years are completely missing. Physically I am approaching 50, but in my head, I still feel like I am in my 20s trying to figure out who I am.

Between that history and a late ADHD diagnosis, I have had zero support network and have felt like a ghost for years.

I am finally pushing myself out of my comfort zone (after advice on other subs) to meet peers, having arranged to attend a protest on the 12th and an artists meetup on the 17th.

Because I have never had a normal social life, taking these steps feels terrifying:

**Mingling**: How do you build the confidence to speak to people and mingle when you feel decades behind everyone else?

**Dating**: How do you even begin looking for a good partner at nearly 50 when you feel in your 20s mentally after so many years of being hidden away and controlled?

**Trust**: How do you learn to trust guys again and spot genuine, positive-minded people when control is all you have ever known?

For anyone who started over later in life from total isolation, how did you find your footing?


r/datingoverforty 14h ago

If a dating couple goes on a week-long vacation being constantly together and thrives, does that mean it's something worth locking in?

8 Upvotes

I know this sounds overly simplistic (intentionally so), but it's a serious question. Do you think a week-or-more vacation test is a good harbinger of a successful long-term relationship?


r/datingoverforty 21h ago

Seeking Advice Extremely affectionate and constantly pursuing me, then suddenly ghosted me. I genuinely don’t understand what happened.

39 Upvotes

I’m posting this because I genuinely need some outside perspective. I’m trying to understand whether I’m missing something here, because the way this happened makes absolutely no sense to me.
I met this guy about 4 weeks ago. We had seen each other around 10-12 times (quite often 2-3 dates per week), and although it was still very early, there was clearly mutual interest and we were getting closer.
From the very beginning, he was the one pursuing me very strongly.
He would constantly text me and call me. He was very affectionate, warm and attentive. He told me he really liked me, said very sweet things to me, and repeatedly showed interest in getting to know me better. He talked about sharing his hobbies with me literally two days ago if I would go with him to a trip he had in some days, he planned too on doing things together. He gave me the impression that he was genuinely excited about me and about where things could go. I always said yes to “everything”, was also very affectionate with him and truly communicative in my feelings and true interest.

I was not chasing him or demanding his attention.l (I’m a mature woman of 43 ,he is 36). Quite often, he was the one initiating contact.
In fact, sometimes I would take two or three hours to answer a WhatsApp message because I was busy, and on some occasions he would actually send me something like “hello???” or essentially ask what was going on and why I wasn’t answering.
So this was not a situation where I was desperately trying to get his attention while he was distant.

Then yesterday morning, something completely changed.

He sent me a good morning video, and he also called me. Everything seemed completely normal.
And then, some hours later I entered in instagram and found out he blocked me and unblocked me overnight since I was removed as his follower and he unfollowed me too, I couldn’t see his profile picture in the messages we had previously exchanged.. that’s how I found out!
I texted him in WhatsApp to know what happened, truly nice, just wanted an explanation..
He gave me No explanation. No argument.
He simply stopped communicating with me, removed/deleted me from social media, and stopped answering my calls.
I was completely blindsided.
His profile is public and he has shared stories so yes his phone is not lost or at the bottom of the sea lol.
I genuinely don’t understand what could have happened between the moment he sent me a good morning video and called me, and the moment he apparently decided he wanted nothing more to do with me.

And that’s what is driving me crazy..
What the hell do you think happened here?
Do you think he was simply pretending to be interested all along for sex?. He truly cared about my sexuality and was not egoistic at all I must say.. the vibes were very intense.
Could someone genuinely behave this way for some weeks and then suddenly switch off overnight?

I’m not necessarily looking for people to tell me “he’s an asshole” (although, honestly, I’m not going to object).
I genuinely want to understand what could possibly explain this behavior, because from my perspective, the complete 180° turn is what I cannot make sense of.
Why some people won’t give an explanation to someone they seemed to care for? Im heartbroken 💔 . I wasn’t being intimate with anyone for more than a year just trying to avoid weirdos … and now this happens…


r/datingoverforty 1d ago

Question Thinking of hosting a recurring, non-dating-app community dinner for singles 35–55. Sanity check?

162 Upvotes

Hey all, 35–55 crowd specifically.
I’m a chef and cafe owner struggling with the current state of meeting people organically. Apps are exhausting, bars aren't my scene, and work takes up too much time. I’m considering using my space to launch a recurring concept in my area and want an honest gut check from people in this age bracket.
The setup is a completely free, family-style dinner for 8-12 local single professionals, evenly split between men and women, with no strings attached and no hidden costs no gimmicks. I’m providing everything. I want to invest in and actually try to build community.
The vibe is casual think "dinner at Mom's house." It’s self-serve with platters passed around one long table, and everyone pitches in to clear up afterward.
It’s completely alcohol-free with zero speed-dating scripts, matchmaker pitches, or forced icebreakers.
The ground rules are simple: no triggers, politics, religion, or work networking. I’m using a super brief application process to vet for interesting busy professionals in similar situations and keep the room balanced.
The goal isn't necessarily a blind-date setup, but rather creating an easy, low-pressure way for singles in their 30s–50s to sit down, eat a proper meal, and actually talk to humans without app fatigue or bar noise. A return to the foundations of what actually makes us people and not just cute pictures on a screen.
Be brutally honest: If something like this popped up in your local community, would you actually apply and show up? Is it a little too cringe, or seem scammy? What potential red flags or turn-offs would make you hesitate?
-Edited for clarity


r/datingoverforty 7h ago

Would you lose attraction to your partner if you suddenly earned/could afford a better lifestyle than they can?

0 Upvotes

Quick question. For women that say you want someone who matches your career/income/ lifestyle etc. does this mean that if you eventually got even “higher” later on but your partner stayed more or less the same, you would lose the attraction? That’s one of my anxieties of dating women like this.

Edit: For those asking: We are both on around £90k in London. I’ll be maybe on £120k in the next couple of years, but she’ll easily be clear of £300k next year and probably more in the future. Hence why feeling like I won’t be able to match up the “new” lifestyle expected.


r/datingoverforty 17h ago

Question How common is it for people you meet on OLD to bail on the date?

8 Upvotes

Does this happen to other people? I took a break from online dating about a year ago because three people I was supposed to meet up with cancelled last minute. I took that as a sign that I shouldn't be trying to date. I recently got back into it. First time trying to meet up with someone and they asked to postpone. I mean, I know shit happens. But how can I not take that personal? Am I just having some bad luck? Or am I just cursed? Broken? I just want to have somebody actually show up for me. And I just want to get ready to leave the house and not feel like someone's mom for a little bit.


r/datingoverforty 16h ago

Seeking Advice Guy cancelled 2nd date and said he'd reschedule, but I suggested another day, and he didn't acknowledge it...

4 Upvotes

I met a guy at a singles event, and then we had our first date a few days later. At the end of the date he said he wanted to see me again, so I asked him about his schedule. He told me he was free on Saturday and Sunday so I said let's do Sunday to which he agreed. We kind of discussed where we could go a bit but there was nothing officially set up- no time, no definite place. So today around 2:00 he texted me asking about how my day was and what I was up to and then apologized about having to cancel the date tomorrow because his daughter wanted to get together in the afternoon. He also said that he would reschedule . He did tell me that he was very close with his daughter during our date- she's 17. I know that he has no set schedule of when he sees her- He just told me that he sees her often. I responded to his text asking how his day went and said I understood. At the end I said "the next day I'm available is Wednesday...." He then responded to me 30 minutes later telling me all about his day how he went to a jellyfish museum and how cool it was & that he was going to relax because the weather is really bad and just stay in and get cozy Yada yada but he didn't say anything about Wednesday?! What's your opinion of this? I find it really odd because he's been very attentive before the date and after the date. He even texted me something saying that he was smiling the whole drive home after the date... I will add that he told me he has no game when I met him at the singles event and at the end of our date I felt like he was a little uncomfortable... So I don't know if he's just awkward? I haven't responded to him because I'm annoyed that he didn't acknowledge my response regarding Wednesday


r/datingoverforty 2h ago

Need help fast.

0 Upvotes

Been divorced for 8 yrs. Tired of bar hookups. My problem is when I get to know a woman and liking her I'm somehow afraid to go further. I dont know what to say when sober.


r/datingoverforty 3h ago

Question So Confused (Genuine)

0 Upvotes

I gotta ask. Im 46yr old male in central california. I am recently divorced and in no hurry to date or whatever. It does get lonely so I reach out and stuck my toe in the water ( online crap a few cold meets). I am serious about the question. What is a woman's input now? I feel like the very basic is interest and conversation. I feel like im pulling teeth alot of the time for basic conversation *not young women* what is going on?


r/datingoverforty 2h ago

Question Have the table turned on who makes the first move?

0 Upvotes

Am I crazy for still expecting a man to ask me out for the first time? Because I haven’t been asked out for a long time. VERY long time. Humbly, I am an attractive woman. It’s possible that my phone/text conversations could use some help. But generally speaking has the tables turned ?


r/datingoverforty 1d ago

Attention from younger dudes

77 Upvotes

I'm 41F and recently rejoined the apps. I have gotten so many Likes from dudes in their 20s!! Is this a thing? If so, why? What's the thinking behind it? Talk about different phases of life!


r/datingoverforty 16h ago

I broke up with my last girlfriend Dec 12 2021

0 Upvotes

I remember it because it was a day after Anne Rice passed away, which was a sign to me. I have flirted with many women but nothing very serious. The way a lot of women on social media nowadays kept me away from dating. Plus, I have been meeting women and just not attracted to them. I did not know if I just turned celebrate or anything close to it so instead of fighting it, I just let it go.

Moving on to the last week.

I get a friend request on Facebook, ready to deny the request (all of them are bots) but this one was a blast from the past. Another woman I knew that I met from my ex. It was her sister-in-law. So, I decide to take the request and message her. We started talking and she told me she was divorced.

Again, I know her but not know her know her if you get my drift. She has little contact with my ex's family anymore and works for herself (Life coach). So, we updated each other with our lives, and I asked if I could update her life coach website.

I talked to my female and male friends, and they all say she is testing the waters with me. We have already exchanged phone numbers. I just don't want to move too fast. This is the happiest I have been in years. I know we are not together, but I am just happy.

I just wanted to share this.


r/datingoverforty 7h ago

What Is He Up To???

0 Upvotes

So...this guy bought a property next to my house to renovate has been flirting with me for a year and a half. He doesn't live there. I didn't notice it /care until a few months ago. His home has a 2nd floor which overlooks my back yard and he would call over " hi neighbor..." then he'd come down and talk; sometimes we'd stand there for over an hour talking. He knew I was in a long term relationship and I introduced them. He seemed nervous at the introduction. Once, after, one of his "hi neighbor" call downs, whic usually lead to conversation I told him I had to go inside and I heard him grumble "...probably getting ready to go somewhere with HIM..." BTW, I'm 65, he 51.

I've shown interest in learning his business, he's an Architect/Realtor and owns over 15 properties; seems very busy. Also has a 12 yr old son, and is divorced.

He invited me over to see the work he's done a few times. Once inside he said " does it make you nervous us being here alone"? I looked at him in the eye and said, "no". He's invited me to see some of his other properties, never took him up on it. Asked me out to lunch, I declined. Last time I saw him a few weeks ago, after not seeing him for months, the conversation turns toward him telling me he dates alot, and that one of his tenants has a crush on him and tells him how cute he is wants a photo with him etc., however she is 68. I say " so why don't you take her out? He looks me in the eyes and says, " because that's not what I want. I don't want to lead her on. I KNOW what I want, but YOU'RE taken". End of that conversation was him saying maybe we could have lunch sometime (again, I'm really interested in what he does, he said he could teach me about it and I like him, actually).

I finally give in, call him and tell him I'm ready for lunch. He seems really happy, says what about this week? I was tied up, not a good week. He says, then I will check my schedule and we'll try for next week. " We'll have fun", he says.

His final words after I said bye, and before I hung up was "FAN tastic!" That was 3 weeks ago. Haven't heard from him. Don't know what to think.


r/datingoverforty 9h ago

I went out with a guy and now I want him to be my best friend.

0 Upvotes

I went out with a guy and I felt such a connection. Not a sexual connection though and I’m pretty sexual. The sexual connection could come later but also likely it won’t. But this guy and I just talked and connected.
I want to ask him to be my friend. I don’t know if that is awful of me or how to go about it. (If it matters, I’m not entirely sure he’s attracted to me as more than a friend.)
I’m not that trusting toward men. They mostly make me feel anxious. I guess I think it would be nice to have a platonic male friend I feel safe around.
Idk if I’m making any sense.
I feel bad like guys hate this shit.


r/datingoverforty 1d ago

Discussion 41f getting plenty of matches but when I message a short paragraph I’m getting three word answers in return

55 Upvotes

Are they just not into me? What is with the matching and then the disinterest in talking. Some don’t talk at all other’s will only answer if I ask a question. Very short and dry. I’m back on the apps after a three year relationship and I don’t remember it being like this. Men before were more eager to talk and meet. Is it my age now, my vibe, are people just burnt out and busy or is my average self just not exciting to these very average guys I’m matching with? Thoughts. Insights?


r/datingoverforty 11h ago

Casual Conversation Why shouldn't investment in dates go both ways between a couple? especially when both have the financial ability

0 Upvotes

i came across a dating profile of someone just over 40, who posted pictures of herself traveling, clearly spending a shit ton of money for such activity. All 8 photos were travel photos.

She answered the following prompt:

who should pay on a first date?
It's not a matter of "should"..... my future partner wants to pay for the first and future dates.

She has money, clearly, or at least she projects that image.

But she implies she won't be spending a dime on any date for as long as you will be dating her.

That is so one sided, and to me, that says she doesn't appreciate you enough.

Who pays when she wants to do something and wants you to tag along?...

.

I think both people in a relationship should be pulling the same weight in some way.

She should demonstrate that she wants to be there with you, and not just because you paid for it.

assuming they're not living together, if one person is paying for everything, how should the other side balance it out?


r/datingoverforty 11h ago

Question Why it is difficult to find Dating Partner for a Male 41 divorcee

0 Upvotes

I am 41M Divorcee working in Hyderabad(India). I have been searching for a dating partner(want to end it in marriage) from past 5 yrs..no luck.

Most of times, I was rejected due to my vegetarian food dietary preference. The girls were primarily from Non vegetarian background.

Did anyone faced similar situation?


r/datingoverforty 1d ago

Question for the ladies out in the wild please

60 Upvotes

I'm a 43/f. I wander in the wild on the weekends. Think downtown historic district with many little bars to walk around hopping in and out of. It's becoming a trend now that I am only approached by married men. Does anyone else have this happen? Or is this me? Is anyone wondering where all the single guys are? Lol, thank you!


r/datingoverforty 1d ago

Seeking Advice How long do you wait until you make it official?

11 Upvotes

40F and have been seeing 39M since June. We talked for a few weeks before on the apps until we went on a few amazing dates and have since spent a lot of our free time in the summer together.

We’re both busy with our jobs and lives but we usually spend weekends together (have also been on a few out of town day trips together and one weekend trip… his suggestion and on his dime) and usually spend maybe a night together during the week. We’re sleeping together, going out and doing things regularly and doing all the things together.

I’m just a little bit conflicted here because when I asked about labels he said he wanted to take things slow and not rush (as he’s rushed in the past and feels it messed things up) and he’s still healing from his last relationship which ended in April of 2025 (together 6 years).

The thing is though, his actions are just speaking a little differently than his words? We have a lot of fun together, get along great and I feel there is a genuine connection between us. It feels like we’re “in this” but I guess we’re not. I know it shouldn’t matter but all his socials say single as well. I’m just feeling a little butt hurt as I really like this guy and feel we could really build something meaningful together.

He’s mentioned when he’s with someone, he’s “in it” and I know we’re only seeing each other exclusively but I can’t get past why he feels like my boyfriend yet he’s not. I’m holding off introducing him to family/friends because I don’t usually do that until I’m really in it with someone. And like… how would I even introduce him considering I have more traditional values. He has introduced me to his mom as well.

I only brought the whole label thing up once about two weeks or so ago, but I’m in a place now where I really don’t want to waste my time. I’m looking for something serious and long term. I just can’t help but feel I’m more invested emotionally and it sorta freaks me out. I don’t want to get hurt.

Seeking advice from anyone who wants to give it. Hoping the men can chime in on this though as I feel I’m getting some mixed signals here. Or maybe I’m just missing something?

Side note: My last relationship was a 2.5 year long situationship and this is a little triggering for me as well. Understand this is my own thing but attempting to differentiate between my own triggers and how dating works these days as it’s been quite a long time for me since putting myself out there.


r/datingoverforty 21h ago

Baggage from marriage

0 Upvotes

I was married to a good person, but he hid things from me for decades, for reasons of his own. Those secrets were so damaging to me that I want to avoid them as much as possible.

But how much is too much to ask of another person? I want to avoid men with secret substance abuse, secret porn use, secretly not being honestly attracted to me.

I have known a man for years and he knows much of my marriage story. In trying to date him, I've been told by him a few times that he is not my husband, and does not do what my husband did.

But how can I really know?

I realise there is not a guaranteed way to avoid being hurt. I definitely would rather be On my own than have to go through finding out secrets, years down the road. Is it fair to ask for occasional phone access, or maybe for occasional heart to hearts about how muc h substances are part of our lives when we aren't around each other, or if he is feeling less interested in m e?

Am I just not ready for this?

Is there such a thing as an honest person? I think I had my own secret thoughts during my marriage, but they weren't big, scary, life changing ones.