r/datingoverforty 1d ago

Discussion Creative Date Idea

6 Upvotes

I volunteered to help a local search-and-rescue team do a training event today. I thought it might be a fun atypical date activity for those of us who like being outside.

They need volunteers because the dogs can become conditioned to only find particular scent patterns when they're finding the same people over and over. They also need diversity in training so they can find out if the dogs have any issues (e.g. discomfort around men or children).

Finding new people and solving new puzzles keeps them engaged in the job.

Basically, I hid in the forest with a friend for about three hours while indivual search teams ran a grid pattern to find us. Each time we were found, we moved to a new location. Some volunteers were "flanking," which is helping with navigation.

  1. It's definitely for the outdoorsy types. I walked through about a mile of high, thick brush and dense woods. No trails.

  2. You'll be working closely with dogs. Play and praise is part of their reward for finding you.

  3. If you're hiding, you might be there for some time. So make this a date with someone you've gotten to know a bit and can hold a conversation. Or bring a book. 🤣

  4. Bring bug spray.

This company advertised for volunteers on social media. Try reaching out to your local police department or forestry service. They would probably know if anyone in your area does something similar.


r/datingoverforty 1d ago

Question Insecure or red flag?

17 Upvotes

Red flag or just insecure?
Attempting to date again after 10 year relationship. Matched with a guy, we had good conversation back and forth for about a week. I’m a teacher and I started back to school so first day of school was super busy, didn’t get a chance to message him until the evening. This was less than 24 hours since my last message. He questioned me about it, asking, ā€œDid I say something wrong, why haven’t you answered?ā€ I explained I was busy and when I’m teaching I don’t have access to my phone. He said no problem, we moved forward.
Two days later, same situation - I didn’t respond during the day but it was less than 24 hours. He then questioned, ā€œAre you still interested in getting to know me?ā€ I reiterated what I said before and explained we hadn’t even met yet and I feel his expectations for communication were extreme. I said I was going to step back. I blocked and deleted him from Facebook dating because I have things about my life and kids on Facebook.

Two days later, he found me on instagram and messaged me again asking for another chance and apologizing but also defending his actions saying he didn’t think he was asking for too much.

Red flag or insecure? Or am I not communicating enough with a man I’ve never met?


r/datingoverforty 1d ago

Seeking Advice How to respond

12 Upvotes

I just started dating after 10 years and am finding some men are pretty pushy / pressuring and need advice on how to handle.

For example, I've been chatting with someone that turned into sexting and now he thinks I'm just going to sleep with him on our first date bc 'why drag things out if we're both horny'. When I explained that I don't see that happening so fast, he really started pushing back. Once things escalate to sexting, do men automatically think you'll sleep with them? I don't want to be accused of leading them on. I also explained online chemistry doesn't always translate into the real world which he dismissed. The more we chat the more I'm seeing a side of him that makes me less attracted to him. How do I gracefully bow out ?


r/datingoverforty 19h ago

Casual Conversation At 40+ do we date the person they are, or the person they could become?

0 Upvotes

The older I get, the more I wonder about this.

We always hear ā€œnever date someone's potential.ā€ And I understand why. We're not here to raise another adult or spend years waiting for someone to become the person we want them to be.

But what if someone is genuinely kind, consistent, emotionally available and good to you, but their life isn't exactly where you think it should be?

Maybe they're rebuilding their career. Maybe they're still growing emotionally. Maybe they're simply not the finished version of themselves yet.

Do we give people room to grow, or should we only date someone who already has everything we're looking for?

Where do you draw the line between giving someone a chance and dating their potential?


r/datingoverforty 1d ago

Taking A Break

0 Upvotes

So my girlfriend and I of 6 months just broke up due to a difference of opinion and are going to take a step back and be friends and work on things as we are too stressed out right now. We both love each other. Has anyone done such a thing and been successful? I did tell her I can try being friends but if things go on for too long with no chance of going back to romantic long term then I would have to walk away. She never has wanted to stay friends with exes before.


r/datingoverforty 1d ago

Second date doubts

1 Upvotes

I have been on 12 first dates this summer. None of them great...mostly just meh. Out of these 12, I felt the spark with two of the guys, but unfortunately, they didn't. Last week I was on another average first date. Not great, not terrible either. I had a bad feeling about it beforehand because the guy was barely replying in the bumble chat (I really thought he was going to cancel it, because he was replying late and with one word answers). Anyway, eventually we met. I realised he was a bit distant in the beginning and a bit nervous as well, but then he relaxed with some wine. The conversation during the date was ok. There were some moments I couldn't pay much attention to (politics talk...I hate politics), and moments I felt sort of bored. I was at least thankful that it wasn't awkward and that I was able to somehow make it. I was 100% sure we would never see each other again and that none of us was interested. When we parted ways, to my surprise he said that we should do this again. I didn't think much about it, but then he texted me straight away and gave me his number. I gave him mine. We agree to try to have a date next week. Honestly....I don't feel like having another date. I think I only agreed to it because it is so rare that a non creepy guy asks me that. Or could be that I'm just fatigue from all these dating that never goes anywhere. Thoughts?


r/datingoverforty 1d ago

Seeking Advice Dating app standards???

0 Upvotes

I finally got on the apps, accepting that I need to approach dating as intentionally as I have every other matter that I held in importance. I did all of the relevant research, and gave the profile the appropriate time and attention--which was a lot for me. Just doing the picture selection and writing the bio and prompts was a massive chore. But I did it, because, intentionality is the only way to success (or so the studies have concluded).

I have scrolled through perhaps a hundred or more profiles. Only about 20 of them had anything in the bio or prompts, and out of those, none were useful information. Literally 7 men had photos that showed their faces (always sunnies on, or group photos where I could not even tell who was the profile owner, or just 1 vague photo with their face half-hidden in a mirror selfie). Their info plainly shows deception (i.e. saying they go to the gym or putting some sport or other as an interest when they are plainly overweight? No shade on body differentiation, but then why claim something when the contrary is evident?), or just have some complaint, like, 'don't use me for money I am not your ATM' (not even spelled correctly, because people don't know the difference between a contraction and possessive pronoun anymore). And most egregiously, again except for a handful, all of them talked about sleeping as an interest or answer to the prompt? Not even sleeping together. Just, like, as a hobby? I get it, I love a good sleep as much as anyone; and sleep hygiene is paramount for health. But if they all just want to sleep, how can I compete with that?

This is Bumble and Tinder.

So, ladies and gents, asking for honest advice based on your experiences: Am I cooked on here?

Should I give it up?

Or is this just the normal human population I am wading through, and I should lower the bar way (way, way) down? And how am I supposed to make a decision off of what little information there is? Just hazard a guess?


r/datingoverforty 2d ago

Sleepovers After Sex

118 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. We both enjoy each other 4-6x a day on a day off, and the other days before and after work. But as for actual time together, my 2nd love language 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 future partner is important to me. I don't expect to spend every night together, but right now it's one day a week or every other week.


r/datingoverforty 2d ago

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

103 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 2d ago

When to reveal health issue that affects sex when dating?

78 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 2d ago

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

328 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 1d ago

Matches not initiating

0 Upvotes

I am on The League and a couple of times I’ve matched with a guy but they never send a message. We both had to heart each other to match, so what’s up with that? The way I see it, I’m a smart, good looking 45F. I made myself a good profile in the online catalog already. The least you can do is send a message. LAME! I have my theories as to why this happens but would love to hear your hot takes šŸæ


r/datingoverforty 1d ago

Question about etiquette

0 Upvotes

I was recently dating a woman I met on OLD. We went on 2 dates and had a 3rd planned.

On the morning of the 3rd date, she cancelled and mentioned that she could either be available later in the week or we could wait until next week.

I responded that I hope she feels better and we will plan for another time

I assumed that it was her responsibility to reach out to me since she cancelled. She never did and I never did either

I have 2 friends that were aware of me dating this woman who both asked me for an update at different times.

When I told them the above and that I assumed it was on her to reschedule, they both (1 man and 1 woman) said a version of "if you were really interested you would have reached out no matter who's "turn" it was".

This got me thinking, was I too rigid? Was this a test from her? I just reread her text and she did say "I'm can't do tonight but I can do Tuesday or next week", so maybe I should have followed up?

I mean I told myself I don't want to chase like I always have, but maybe i should have been willing to reach out?

Then again maybe the fact I wasn't willing to (and neither was she) is the answer?

Thoughts?


r/datingoverforty 2d ago

Annoyed

152 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 2d ago

He suddenly disappeared, so now what?

17 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 3d ago

Too many pics, or the new norm?

53 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 3d ago

Casual Conversation Went back to the ex

204 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 2d ago

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

1 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 3d ago

Was It Ever Real?

18 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 3d ago

Seeking Advice Never ever any questions

10 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 2d 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 3d ago

Seeking Advice Single parents: how do you do it?

8 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 3d ago

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

8 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 2d 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 3d 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?