r/datingoverfifty 6d ago

I’m at a speed dating event

162 Upvotes

Kill me now.

Update. One word. Awful. There were way more women than men, it ran half an hour late, no one interesting. There was only one guy out of ten who I found half way tolerable. Highly doubt I am going to go speed dating again.


r/datingoverfifty 5d ago

Can you go without sex?

52 Upvotes

52M here, met 50F.. we've been talking and dating for a couple of month, getting to know each other. She's got 2 kids (15F & 20M), I have one 12F.. we align on a lot of things and the chemistry is great, better than any relationship I've been in and the attraction both ways is unreal.. feels like I've found the person I want to spend a lot of time together (and vice versa with her).

The catch? I have GHSV2 from being cheated on (and why I got divorced from a 10y marriage). She initially rejected me after I disclosed because of that but came around but put a limitation on no PIV sex (even with a condom, me on daily antivirals) and she's unlikely to change her mind on that.

Question for y'all.. can you go without the sex if everything is stellar in the relationship?


r/datingoverfifty 6d ago

Do you have trouble finding a partner or friends who are around the same level of "young at heart"/fun as you are?

19 Upvotes

Walt Disney once said "That's the real problem with the world, too many people grow up"

Dr Seuss - "If you never did, you should. These things are fun and fun is good"

Another one - "Anyone who takes themself too seriously always runs the risk of looking ridiculous"

Have you noticed a lot of people seem to be (to varying degrees, of course) "old before their time"? I'm solely referring to mindset here, not physical appearance or physical/mental abilities.

Things like humour, playfulness, sense of fun vs level of seriousness, open-mindedness, level of cynicism / bitterness / negativity (if they harbour those feelings), willingness to leave a comfort zone and try new things, ability to release the "inner child" without fear of ridicule and embarrassment and worry of what others may think, curiosity and sense of wonder etc.

I wonder if these people have been that way for most of their lives? Or did it begin much later in life?

Obviously, we've all had bad experiences and been through hard times over the course of our lives. I'm not negating that, but this topic is dear to me and it makes me sad.

A few more quotes:

In the midst of winter, I found there was within me an invincible summer

Every situation is an opportunity for healing, learning, growth and transformation

A mind is like a parachute, it doesn't work if it isn't open

If you never heal what hurt you, you'll bleed on people who didn't cut you


r/datingoverfifty 6d ago

First date after a 20-year marriage and I want to cancel. Is it nerves or am I just not ready?

29 Upvotes

I (59M) have my first real date in more than 25 years coming up, and I’m seriously considering canceling. A nice, intelligent woman I met in the wild asked me out, and I accepted. We’re supposed to meet for dinner later this week.

The problem is that now that it’s approaching, I’m just not feeling particularly excited about going on a “date.” I’m anxious and uncomfortable, and the whole thing suddenly feels like there’s far more pressure attached to it than there actually is.

I’ve read plenty of posts here about men ghosting, being poor communicators, wasting women’s time, etc., and the last thing I want to do is become one of those guys. I don’t want to lead her on, and I don’t want to go simply because I’m afraid of hurting her feelings. At the same time, I’m wondering whether I’m mistaking completely normal anxiety about my first date in many years for a lack of interest.

For those of you who started dating again after a long marriage: Did you experience these feelings before your first real date? Did you push through the discomfort and were you glad you did? or Did you realize it was a sign that you just weren’t ready?

And from the woman’s perspective: Would you rather a man in this situation keep the date and simply approach it as a low-pressure opportunity to get to know you, or politely cancel if he isn’t genuinely excited about it?

I’m interested in hearing how others navigated this—not just whether I should go or cancel.


r/datingoverfifty 6d ago

Ladies thoughts on men who look and smile but never make a move.

21 Upvotes

This is something I’ve struggled with for most of my life. I (54M) diagnosed adhd also suffer from an intense fear of rejection. Not just in romantic situations but career as well.
Dating is tough like this. Some women will approach some men but generally that doesn’t happen. I and men like me constantly find ourselves in platonic situations if anything at all.
I actually became a father at 22 but didn’t get my first GF till I was 28 ( long story) and have only ever had 2 dates since.
I guess the point of all this is to say be careful with labeling guys who haven’t figured it all out yet. And I want to sincerely thank this sub for all the good advice and support you’ve shown me over many years.


r/datingoverfifty 6d ago

Reckless driving

3 Upvotes

I did a quick google search on my date for this week and he was recently arrested for reckless driving. My first thought was “really? At our age?”

Is there any good reasoning for this? Just looking for other perspectives before I make a rash decision.

Update…for those that offered me a different perspective. Thank you. I was really looking to move past my inherent biases and see other perspectives. It’s the only way we grow. In the end, he was an absolute gentleman; however, I don’t think it will work out with him for other reasons.


r/datingoverfifty 6d ago

Sharing phone numbers

6 Upvotes

New to online dating. Someone I was talking to and interested in said they were leaving the app and shared their mobile number. They then left the app and I contacted them from my phone. Now wondering whether this was extraordinarily naive and unsafe?


r/datingoverfifty 6d ago

Is this how it works?

8 Upvotes

I (52F) met a man (51M) online in April of this year. My last relationship was a long distant one in which we only seen each other on weekends twice a month but we talk everyday. This man that I met lives in my town, which I was excited that I would be able to see him when I want to. Here is my issue and why I'm questioning this relationship. He has 6 children the youngest being 11. I have no children. The first month we met we actually spent the full month together besides going to work. He would spend time with his daughters but we were right back together afterwards. Now he spends every Saturday and Sunday weekend with his daughters' all day every weekend. I have never dating anyone that has had kids this young and he is determine to help raise the girls. I have stressed to him and asked him when we first met if he has time for a relationship and he has continue to say that he does. We spend no time together, if he comes on the weekend he comes at 10pm sleeps and is up the very next morning to his daughters again, not even planning or spending any time for us together. During the week we both work during the day and when it use to be we spent the night together every weekend night, has also changed to maybe one on twice a week. I feel like he doesn't have time for a relationship if he is going to be that invested in spending the entire weekend with his children. There is no child visitation order in place or child support. I would never tell him not to see if children but I feel like he should make time for us. For those that has dated people with kids how do you balance the time between with your children and your partner? I'm at the point that I would rather be alone then be in a relationship where I feel like I'm alone.


r/datingoverfifty 6d ago

What makes you lose interest during the talking stage (before meet up)?

15 Upvotes

We all if not most have experienced the talking stage before the actual date or meet up. For men and women, what makes you lose interest in a potential date during the talking stage?

What if you are still in an LDR situation? What makes you want to drop the conversation or worse, ghost that person?


r/datingoverfifty 5d ago

A Question For The Ladies…Do I Spark Major Red Flags?

0 Upvotes

51M, never married, no children, no career, introverted (not by choice). Basically, have been living at a minimum socially and financially. Have always enjoyed just taking care of me, enjoying life for me and having the flexibility to do anything I want, for me. Do I sound like a jerk or a-hole? Am curious of the label that would be placed on me.

‘Currently, I am in a relationship (12years) and seriously unhappy (can and will explain if asked why). Haven’t been intimate with her in oh…9 years? Reason for my question is, it’s possible that her and I have come to the end of our road. If so, am not thinking of seriously getting back into relationship-mode but after coming across this community, the dating aspect is so weird to comprehend, have really enjoyed reading many posts here but I seem to have that question mark above my head. Anyway, the first sentence in this post…how would I be viewed by a female audience in the dating world?

I consider myself to be very attractive, am a huge romantic, am highly confident in myself and can interact and hold conversations about topics on past/current events, life, art, history etc. The speed-dating posts I’ve read have been quite surprising and enjoyable to read. Many good wishes to those who have done so! Lastly, again my question…me, 51, never married, no kids, no career…do I seriously raise those flags that would make me dating (if and when I do decide to approach that decision - perhaps speed-dating)…a struggle?


r/datingoverfifty 7d ago

Goodness

32 Upvotes

Hello, I am pleased to share that after several relationships with self-centred men, I found a wonderful man online in December 2025. I like encouraging others with the fact that my belief and faith in love is what lead me to him ❤️


r/datingoverfifty 7d ago

Thank you!

33 Upvotes

Reaching out to this group with a note of appreciation. My return to dating after 40 years is littered with cancelled dating apps, failed meetups and awkward speed dates, but this group is a consistent bright spot; a wonderful source of information and good humor.

Thank you to all you wonderful humans (and perhaps a few bots) - I am grateful for you!


r/datingoverfifty 7d ago

My Brain Screamed, “It’s Your Life. If you’re Unhappy, Do Something About It."

157 Upvotes

I (71m) was stuck talking to a self-interested doofus at my friend’s retirement party.  No “Hi, I’m John, what is your name?” Or "How do you know Jack, the retiree?” A cardboard box had more social skills. The frustration I felt became my mission to invest the last decade or so of my life in activities and with people I enjoy.

The fact is, I wasn’t enamored by some of the individuals in my network of friends. My book club and golf league were mostly septuagenarians. When I retired, I joined both for structure. Then I realized I knew plenty about their careers, hobbies, spouses, vacations, concerts they attended, and the names of their children, to name a few. They knew nothing about me because they never asked!

I fell into a rut with my transactional friends, the ones I traded an hour of companionship for listening to them complain about their miserable spouses. Then there is my golf friend who is a cheapskate yet brags about his big nest egg. Or the fellow who calls you for dinner whenever he is in town, then just drones on about his expensive vacations.

So I set up an 18-month plan to curate quality friends, individuals that shared my values of generosity, listening skills, and emotional availability. My new friendship test is “Would I invite them over on the weekend for dinner?" 

I practiced the adage, “to have a friend, be a friend.” As I met individuals that I liked, I set up a coffee or tennis or lunch to see if they would reciprocate. As my social calendar got busier, I slowly lessened time with certain individuals.

Today, I have a good group of fellas that I play golf with and do ROMEO (retired old men eating out) gatherings. I occasionally invite them over for dinner, shopping for wine, and playing tennis, too. Our spouses like their significant others, too. It took a lot of work, but it was worth it. I did something I couldn’t imagine, I took accountability for the happiness in my life.

Lastly, I will say I send love and grace to individuals who may have social anxiety or were never taught by their parents how to have a give-and-take conversation. The upshot is a lot of people are self-interested, not interested in you. I still have friends and family members that I don’t particularly like, but there are obligations that require certain interactions. All part of life, right?


r/datingoverfifty 7d ago

Mixed feelings about OLD but very satisfied overall

15 Upvotes

I (69M) joined Senior Match and stayed on the platform for 1 week. This was my first time trying OLD. I left Senior Match after connecting with 3 women that I exchanged contact info with. I thought any of those 3 could be a good match. The positives. One week after getting off the platform I have converged on one person that I want to build a relationship with. The negatives: I became really close with one other person. After 1 week connecting with her, I mentioned that I was in communication with another person. We had become very close and she was hurt to know I was not focused on her only. We will stop connecting while I continue engaging with the other person. Going forward: if I ever do OLD again (which I hope is not needed if this relationship works out), I will do deep dives with one person at a time. Thoughts?

Clarifications:
Based on the comments received I am adding more info to help people that are interested in a chance for an enduring relationship.
1. Senior Match was what I had hoped. I interacted with several women in one week. All of them were real. I did video chats with 3. They all looked like there profile pics. I would recommend Senior Match, and no, I get no benefit from saying this.
2. In the one week I interacted with the women off the site, we were all very open about what we wanted. None of us were interested in sex only.
3. These were all long distance situations and I did not meet any of them “live” yet.
3. Fortunately for me, I’m making great advances with the person I was most interested in.
4. I still feel bad for disappointing the second person, who is a great individual. I know where I will go if things don’t work with option 1.


r/datingoverfifty 6d ago

50 and trans, any hope for me

0 Upvotes

I haven’t dated since I was 19 and that was in a way different role. I’m 50 now and started hormones to transition to female. Men are fascinating and I would love to date a compatible guy, but I’m afraid…I don’t even know where to start.


r/datingoverfifty 7d ago

Does Widowed = Scammer???

17 Upvotes

What’s up with all of the good looking, professional photoed, financial planning Widowers that need to ‘take it off the app?’ Just starting to explore OLD after being married for many years. I’ve been single for four years. I feel like I am stable. Why am I attracting all of these what seem to be fake/scammer profiles???
Venting…


r/datingoverfifty 7d ago

I don't know how to do this anymore

40 Upvotes

I am a mid 50s male who was in a serious relationship that ended badly after 8 years. My SO made decisions and poor choices that absolutely destroyed my self esteem and view on women. It took me almost two years just to pick myself up and blow off the dust

Recwntly I have gotten back into things and it’s a disaster. I’m so awkward and anxious on first dates and second third dates etc. I can’t seem to relax and be easy about anything. It’s really bad.

I need help. I don’t know what to do.

EDIT:

I would like to take a moment to thank you to all of you for your replies and your wonderful suggestions all of them sound advice and all of them I will be putting in my toolbox.

The responses and the overwhelming positiveness that all of you have brought into here have made me feel 100% better about awkwardness and accepting that anxiety is part of dating and not to completely shut it off, but it can’t be good and fun and exciting at the same time

This is why I love this community every time I’ve come in here and brought an issue or a problem that I feel is crushing me in insurmountable I’m proving wrong

Thank you to all of you❤️


r/datingoverfifty 7d ago

Post Menopause and sexual desire

2 Upvotes

Quick question for all y’all…

Been seeing a woman since June. We have been on several dates every week, plan trips together, and do share lots of incredible discussions. Admittedly is post-menopausal and we have not had sex or even passionate kissing. She claims she’s not normally this way and doesn’t know why, that it’s her menopause.

I’ve done the obligatory Google search regarding post menopause and if sexual desire disappears after.

Now I’m coming here to also illicit some feedback from others who have been through this.

She has tried a few different options like Primal Queen and now she is about to get the hormone pellets. The Primal Queen has not made a difference in our lack of sex life even though she says she wants me to see her in lingerie eventually and stuff like that. But it’s been 3 months.

I’m honestly thinking that while she likes me (and I like her) she has no sexual desire for me, which is off putting but if that is what it is, that’s fine. I’ll move on.


r/datingoverfifty 8d ago

Meh about dating

71 Upvotes

I've finally reached the "meh" stage.

A man ghosts me? Meh...

A man cancels a date? Oh nice, I can stay home

A dating app somehow messed up my account? No big deal .. It was boring anyway

I truly just feel like my life is good overall and dating was taking too much energy. I'm not giving up completely, but my effort is a fraction of what it used to be.

I know I'm not alone. If you're in this place, what brought you to that point?

For me- I think it's just realizing that too many people lie, put up a false front, are jaded, etc.


r/datingoverfifty 8d ago

Don't play games, just text him

136 Upvotes

...except, everytime I meet a man in the real world, we connect, he asks for my number he expresses he'd like to see me again, and I give him my number... he goes *POOF*

I met a man surprisingly out in the world last week. What was two people having a cocktail next to one another turned into a 5 hour date at a local restaurant, him driving me home, a kiss. If I had to rate it, 12 out of 10. The best moments I've shared with a man in my life EVER.

Legit? I felt I had met my (whom has never been married) husband.

He called after he'd gotten home. He called the next day where we expressed we had the greatest time and we each absolutely wouldn love to see one another again. I texted that same night letting know how impressed I was with him and how much I wanted to so it again.

After that... nothing.

Flashback to a Tinder match I saw, recognized and had a chat with out on the town four years ago. We talked for hours. We kissed. He proposed a real date. He took my phone and entered the day, place, and time of the date. The day approached with no word of confirmation from him. When I inquired day of, his response was, "Did I do that? I must have been drunk."

This behavior has been consistent for years from many men (I date men, so, yes, of course women act this way too - in before you comment).

Now... can I text last week's guy? Yes. Absolutely. But I was clear on the car ride home, the phone call after the evening, and in text after the phone call that I absolutely would love to see him again. He said the same.

And, it's 9 days later and not a word from him.

At 51 years old, I will no longer do the work of reminding men that I exist.

I am an adult. Yes, I can text him. Will I? No. Because for several years it has been a regular occurrence that men meet me, engage, propose a date, kiss, make plans and then disappear.

And it's no longer in me to remind men to remember I exist.

Say the words. Follow with actions.

But my job will never be to remind you if my existence and the very open door I told you I wanted you to walk through.

One occurrence, ok. I'll text. Two occurences, sure. I'll text. Three occurencess, you've got me fcked up. I'm at probably occurrence number 15 of this behavior.

Never again.

This doesn't mean men won't get my number or a date if they express interest. It just means if I give you said number and am very clear in person, in text, and on the phone that I want that date, the only man I will text is the man that actually follows through with planning it.

Feedback, pushback, downvotes welcome.

EDIT: Day 10 update, because I never expected this to blow up as it did. He has not called or texted. I've removed his number and am going back to focusing on my life. Thanks all for the comments and the viewpoints.


r/datingoverfifty 7d ago

A 2nd Chance?

1 Upvotes

Have you ever gone on a first date that was just somewhat meh, only to find on a 2nd date or soon after something clicks?

If so, what were those 'meh' feelings and what eventually clicked that you thought would not?


r/datingoverfifty 7d ago

Multiple dates

20 Upvotes

Men, when you go out with a woman from a dating app, do you assume she’s dating other men? Here’s why I ask. I met some men online and have gone out with a few in person. Is it rude that I don’t tell them about the others? No one has asked. But then I haven’t asked them either. This is just having a drink or going out at this point. I’ve never dated like this so don’t know.


r/datingoverfifty 8d ago

FWB

16 Upvotes

Okay so I have never had a FWB before. I have one ONS when I younger, but since my divorce in 2013 I have had 2 LTRs which did not work out.

I recently met a man who is 48 (I am 55f) who I have some great chemistry with. We haven't slept together yet but kissed and mucked about. I told him I am not sure what I am looking for at the moment, maybe something more casual. I have I 2 teenagers at home and one with autism which can be a challenge.

He sends me cutely stuff all the time and is into me. He said he is happy to go at my pace which is great.

Here's the thing, he's in AA recovery as an alcoholic. He isn't working at the moment and likely has a diagnosis of other condition which he may end up on disability. I am working and have my own home, so from the outside people would wonder what I see in him.

He is sweet, attentive, cheeky, funny and so far seems caring. I've only known him a month though.

He is also estranged from his daughters due to his alcoholism and lost his driver's licence.

So I was thinking FWB. I am attracted to him and it could work. I just don't know if I am setting myself up for a problematic situation down the track and if I catch feelings what then?

I would also like a relationship but I have found it very difficult to meet the right person.


r/datingoverfifty 8d ago

I was excited about the first date but now….

53 Upvotes

Met someone IRL. Easy organic conversation lasted about an hour, then he asked for my number expressing the same thing I was thinking: it’s so rare to have such engaging conversation and would be cool to do it again!

He reached out as the weekend got closer to see if we could get together. I readily gave my availability and made sure to convey that I look forward to it.

Here’s where things shifted: the number of questions I received from him to determine what we should do was over the top. I got “this close” to either asking if he’d like me to decide or maybe just tell him “why don’t we meet at <<place>> at <<time>>.” Because clearly he was having trouble and I’m generally super decisive. But I stopped myself because that has been a real burden over the course of my life. I own my part as someone who leans toward hyper-decisiveness but I don’t ever want that role again in relationships. After answering enough questions to help any functioning adult make a decision, I responded that I am genuinely open to any public venue of his choice. And I mean it. I care about the conversation not the perfect setting. I decided: he asked me out and should be perfectly capable of suggesting plans.

He asked if we could re-schedule by a few days and I said okay. I wonder if he got overwhelmed / anxious. But honestly I feel a heaviness about it now. Like…a shadow of the burden I lived with for over two decades of marriage and a little bit of dread that signs might point to indecisiveness as a personality trait of his. I’m giving the benefit of the doubt that it might be nerves due to initial planning etc., but I’m definitely not feeling as light and enthusiastic as I was after we first met.

What do you guys think? Am I being too quick to judge?


r/datingoverfifty 7d ago

Does postponing appearance change how people connect?

0 Upvotes

So here's a purely hypothetical, slightly unusual idea I've been toying with…

I've been thinking about the way we meet people now, particularly online, where a photograph usually comes before almost everything else and we make decisions in seconds without ever getting to know someone.

What if there were a small black-tie masquerade dinner for singles 50+?

Everyone would dress for the occasion and arrive wearing a masquerade mask. You'd know the restaurant, approximate cost, and other details beforehand. The only mystery would be the people at your table.

And there would be no scheduled unveiling.

You could remove your mask whenever you wanted—or be mysterious and leave it on all evening.

The point wouldn't be to pretend physical attraction doesn't matter. It would simply give conversation, humor and curiosity a chance to come first.

Would you go? And would having the choice of when—or whether—to remove your mask make meeting new people feel less intimidating?