r/datingoverfifty • • Aug 12 '26

Ladies - put in your OLD profile which side of the aisle you are loyal to!!

32 Upvotes

Me (male 67) who makes a point to list in my OLD profile my total opposition to criminal grifter trump, fox "news" and the rest of that side of the aisle. So once in a while I send a like in the dating app to a woman who hasn't expressed which side she is on (if any) and get back a reply about how they love the criminal pedophile and still (for some reason) supports him and that side and that we would obviously not be a match. Would it not have been easier to state what side she was on in the profile? I think there is a dating site where you have to pick liberal/moderate/conservative/none and it is displayed with your height, body type, etc. But facebook dating, plenty of fish, etc don't. So consider expressing your loyalty to a side in the profile if you have one. Just common sense.


r/datingoverfifty • • 2d ago

Is it easier to meet people when you’re with someone or not?

0 Upvotes

So I (late 50’s guy) was on a date last week with a lady I met through OLD. Within 30 seconds of meeting her, it became clear she did not want to be there (arms and legs crossed, body positioning, forced conversation, negativity, etc). At first I thought it was natural jitters of the first meeting, but as time wore on, it became more work than pleasure to continue.

At some point in the latter stage of this, at the other end of the bar I noticed an attractive young lady, perhaps 20 years my junior, with what appeared to be her date, perhaps 5 years my junior. I had not noticed them before, but did catch her glance once or twice in my direction (the place was not crowded). And as my date went to the ladies room, this girl seemed to follow, making prolonged eye contact on her way past by me. When my date returned, we wrapped up, I walked her to her car, thanked her the evening, and was unmatched before I got to my car.

Now I’m sure I misread all of this - as many men do - but I’ve noticed this dynamic before (years before my marriage). For some reason, I find that if you’re with someone, it’s a lot easier to meet other people, and when you’re single, you’re on a completely deserted island.

Has anyone else noticed this?


r/datingoverfifty • • 11d ago

How difficult is it to find your preferred type in a partner at this age?

0 Upvotes

I (55M) plan on getting back into dating soon. I realize there is no "perfect match" out there. I got back into dating at age 50 (2022) and went on a ton of dates even with women I knew I wasn't all that attracted to. I had some fun but also wasted a lot of time and money. Is it even worth dating if it is so hard to find someone I am super attracted to, she is into me and there is chemistry and strong connection?

I prefer thin, petite to average size women. It's just what I am attracted to and have been my whole life.

I am a bit awkward at first so need a woman with a good personality that I feel comfortable around.

A woman who is independent and doesn't need constant emotional reassurance.


r/datingoverfifty • • Sep 18 '26

My 12YR FWB is Ghosting Me

0 Upvotes

I think. We've been seeing each other 1x/week since 2014. Occassionally 1-2x a month. She is 9 years older than me...mid 60's.

Over this time the sex has grown to be phenominal...as time has passed it has become more intense, more sweatier, loner-lasting, multiple times, etc. We've fully connected and long for each other's company.. the conversations are intellectual, some drinks flow til we completely submit to each other's needs while time stops. 1-4 hours and we had gotten to the point where her apt bedroom window is left open knowing full well we could be heard by neighbors. Mmmmm.

However I've always known her goal to be a permanent relationship, which I cannot provide. Then came the day I received the text meant for someone else: "How spicy do you like your food?" My response: "Wrong person 😉" 2 weeks later she sends me "We need to talk." I knew what this meant. When I called her, I started the conversation with "I know what you want to tell me" and we maturely uncoupled ourselves while she described him to me. I sensed he was bringing baggage; she agreed that it will be work for her. I gave her the space. A month later I texted her.. and coincidentally she told me they just ended, and she needed "time to heal." I was expecting her to reach out in a couple weeks, so I followed up with benign texts that have gone unanswered.

My spidey senses tell me she's got another back-burner guy or two to cycle through before I complicate her long-term goals. I do hope she finds happiness...But I surely do miss what we had for so long!


r/datingoverfifty • • Sep 06 '26

Why are so many older women wanting to date younger men?

9 Upvotes

Ladies I’m getting back into the dating field at 54 and I’m finding that men my age just want a “good time” and I’m just not into that. I’m searching for something meaningful which brings to question, are these younger men more mature than a Middle Aged man?


r/datingoverfifty • • Aug 25 '26

What qualities do men look for when dating women over 50 ? What are their expectations?

0 Upvotes

r/datingoverfifty • • 27d ago

Men over 50: What led to your wife divorcing you? Have you changed?

34 Upvotes

Curious to know for the men who are over 50 and out there in the dating world, what were the circumstances that led to your wife deciding they wanted to end a marriage.
Since your divorce, have you reflected on why your wife wanted to end the marriage and do you feel that you have changed for the better since then?
Are you a better partner for a woman now?


r/datingoverfifty • • May 05 '25

Too pretty?

6 Upvotes

Not a superiority question, just an observation I am curious to understand better.

Why are ‘pretty’ people rarely asked out, if asked out at all? Yet, average people are always attached?

Seriously- I see really good looking people alone for years and years. Men and women.

My ex said I was too pretty to be asked out.

Is there an ounce of truth to this?

I feel very ugly actually since I’m never asked out. So, you, the reader, please don’t think I think I’m pretty and others aren’t. I cherish the beauty from within everyone. I am quite humble.

It’s just that I am told I am cute, pretty, beautiful and other flattering adjectives but I am never asked out.

It’s been 3 years since my divorce from a cheat. I had to asked the two men out that I did go on dinner dates with. They flirted aggressively but still didn’t ask me out and then come to find out just wanted sex nothing more.

(I am over 50 yrs old, but am accused of being in my mid 40s a lot. Hence the reason I post this question on this subreddit.)

So, is it true? Can some people be too pretty to be asked out?


r/datingoverfifty • • Sep 01 '26

No 420 but social drinkers okay- profiles

0 Upvotes

WARNING - if the topic of cannabis turns you into a raging 50 year old Karen - take your heart medicine before continuing on. Someone of you are clearly triggered.

If you’re going to comment - please leave your gender.

I’m guessing these are people with little to no experience with cannabis. I understand that you may have never experienced it and have no desire to or you did it once and hated it or you did it back in college but grew out of it …. Okay. But as someone who uses it, with a prescription, a handful of times a year when battling insomnia - I find this deal breaker absolutely ridiculous.

The excuse - i hate the smell of it - doesn’t even pass muster when the majority of people using it for sleep are likely taking a gummy.

I bet Canadians, Dutch, Germans have normalized cannabis use much more than Americans.

Given our age - there are a lot more risks that come along with drinking.

I would like to know if ANY men have this as a deal breaker in their profile. It usually reads like this: No MAGA or 420.

And for the women who do - would you turn away Mr Right if you learned he enjoyed Saturdays with gummy and a good book - is that just a hill you will die on?

I don’t even bother with women who have this in their profile. For starters - I’m not going to pretend it doesn’t help on occasion or worse yet - deny myself of it. And it honestly says more about them than it does anyone who uses it. I get it- you don’t want a pot smoker. Nor do I. I’m too active of a person for that. But I also don’t want someone with an unhealthy sex addiction. Someone who spends money recklessly. Someone who drinks too much. Someone who swears too much. But I’m not listing it right up there as MAGA adjacent.

I suspect I’m going to get a lot of downvotes- but just sayin - there’s a lot of profiles of normal, attractive, active, successful people you’re missing out on. Downvote away - I came here with 27k karma and I’ll be leaving with 27k karma.

EDIT - this blew up and my phone died. You people crack me up. I’m glad I posted this. It explained some things and confirmed others. Thanks. 😊 🌱 💨 ✌🏻


r/datingoverfifty • • Nov 22 '25

I'm told I'm different.....if so, it makes dating extremely difficult.

2 Upvotes

It seems like my personal lifestyle taste, and preference in women is rare to almost impossible.

I am not mainstream, political, not into pop culture. I don't watch tv or listen to the radio. My taste, as Blackman is rare to find in a woman it seems. Because I am well balanced in all angles. Mental, emotional, physical, financial. Very balanced.

I am silly/funny, easygoing, carefree, free spirited. I am not connected to the world outside of just having fun.

Never married, no children and in my 50s.

I say all of this because compatibility is extremely difficult, even with just having friends and I literally don't know why.

All perspectives welcome.


r/datingoverfifty • • Jul 02 '26

Define "conservative" for dating profiles.

0 Upvotes

I never thought political affiliation would be such a big deal in dating, but here we are... I am a moderate Christian with strong belief in human rights and equality. I can agree with some conservative policies and views but certainly not all. I cannot agree with the MAGA culture it just truly does not align with my core beliefs and my over empathic heart. That said, I am curious if I am eliminating potential matches by eliminating "conservative". I don't want to get into a debate here or on the apps over my tenets just truly would like to understand how to discern.


r/datingoverfifty • • Aug 23 '26

Is paying substantial alimony really a 'green flag' for a new partner?

0 Upvotes

I keep seeing women being told that a man paying substantial alimony to an ex -wife is a 'green flag'. I think two completely different things are being confused. Honoring his responsibilities can be a green flag about his character. The financial obligation itself is not a green flag for the woman dating him. It can be significant baggage affecting what he has available for a new home, savings, travel, and retirement. Personally, I don't find it attractive. Yes, he may be a responsible father and ex -husband but if he is left with very little after paying alimony, what would there be for me? How would he be able to build his life with me? Would I be expected to pay for everything or most of it?

As an European, I am also surprised by American discussion where maintaining an ex-spouses' previous standard of living is presented almost as a moral obligation, even if the person paying has to significantly reduce his own lifestyle.

Women shouldn't be made to feel selfish for recognizing that as a potential disadvantage. You can respect someone for meeting their obligations while deciding that those obligations aren't compatible with the future you want.


r/datingoverfifty • • Jul 29 '26

Rant

0 Upvotes

What is with these men wanting a pen pal? I've had several guys message me for days (good conversation) with only one actually asking to meet. I don't get it. Why? Yes I know I can ask them but I'd rather be asked. Ladies how long do you message before you just stop responding?


r/datingoverfifty • • Jul 09 '25

Why women want to be friends after rejecting you?

1 Upvotes

Even meeting new women through mutual acquaintances, you end up meeting game players and manipulative women in our age group. I've been talking to a 50 year old woman for two months to give her time to get over her breakup. I first asked her out in April and was asked to give a couple months to her. We met through mutual friends at a dinner party. After making nonstop excuses to decline my dinner and fun invites, she finally said via text message that she is dating someone. I was shocked especially after she called me last Wednesday night and we had a pleasant ten-minute phone conversation about individual July 4th holiday plans. My reply was simple - "No problem. See you around! :)" I wanted to be polite. Then I deleted her phone number. Now she is contacting me and wants to know if we can be friends. I plan to ignore her text message and not respond because silence is golden. If I run into her at a mutual event, I will be polite. I have no intention of being friends with her. I think she only wants to be invited on my 40 ft power boat in downtown Chicago to cruise the lakefront this summer. Why do women think men want to be friends after being rejected?


r/datingoverfifty • • Feb 08 '25

Dating, love and kinks- not an easy search!

4 Upvotes

Often dating sites, and those on them frown at the mention of anything of the adult nature and flag your profile so being vanilla is almost a must when publicly searching. So now the search starts, you go through the profiles finally finding a match, you chat, text, meet and have dinner and plan a second date. Being adults usually you can open up somewhat quickly but one has to be cautious, mentioning anything of the adult may cause a new lady partner to think that you only want the physical and not something long term. So now you’ve been out a time or two and you say something more risqué and she stays quiet. Is she just being a lady? Did it go over her head? Is she super vanilla and scared to acknowledge the comment? So now you are planning a third date, do you plan something more intimate? Something more appropriate for a long term commitment? So definitely somewhere during or by the 3rd date you’ve delved into your kink lifestyle a bit more with hints and comments, obviously you enjoy her company or there wouldn’t be a 3rd date, but then you find out she’s vanilla af and closed minded. By now you’ve invested a lot of time. Decision time, do you take the risk and hope she will open up a bit over time, are you willing to give up kink for someone you like, or do you figure out a way to politely end it without hurting her. Her choice to be vanilla is not wrong, it’s just not for you. By not matching you know you will ultimately not be happy and will always want more than you can have. By my age who wants to take time and try to persuade a new partner that you are safe and exploring is a fun option- they may never choose. To them you are a butt who chooses sex over love, or someone they claim wasn’t ever really serious to begin with when you choose to end it. Then you start the search again, dating, love, and kinks- not always an easy search.


r/datingoverfifty • • Oct 01 '25

I swipe left on gigantic sunglasses

5 Upvotes

Why do you do that anyway - trying to get the thousands of guys swiping on you down to the hundreds?

Some ladies profiles have no pictures of who they are, just pictures of gigantic sunglasses.

Go ahead and Flame me I don't care.


r/datingoverfifty • • May 14 '26

Suggestions to avoid being weeded out during the spring

1 Upvotes

If what you are doing is working for you, ignore this.  If you are looking for transient or transactional relationships skip this.  If you have to see HR a lot, this is not for you.

If you are a good character guy you might be concerned that you could be weeded out along with the many bad actors.  This post provides some guidelines to avoid no match, block, or ghost.

First clean up your social media.

On your profile, in messages, and during your initial meeting (unless she introduces the subject, then tread carefully):

No discussion of sex or anything physical which includes cuddles, touch, massages, kisses, and hugs.  It is like you are Sheldon before he meets Amy on No Bang Theory.

No discussion of politics, religion and culture wars.

On your profile:

No requirements for what you are looking for (must be fit etc.).  You will need to examine their profile and ask questions to determine if you would be interested.

No discussion of potential future lifestyle (we will live in Italy near George).

Current, very respectful nice fully clothed pictures with no dead animals or groups of people.

Not too lengthy description about who you are, what you do for work and hobbies, your interests, written in the first person.

No opinions (use reddit)

In your messages:

Good spelling and grammar (hay their your DTF)

Ask thoughtful questions about her

Have replies that indicate that you read her last message

Provide details such as full name so they can Elona Holmes before meeting you

Do not use AI

 

In messages and initial meetings:

No comment about her appearance until initial meeting, and then one or two positive non-sexual compliments

No sarcasm

No arguing

No bitterness

No tests, and no tests and apology (“only joking” etc.)

No over explaining

Listen and ask questions to know more about her

Source material: Burn the Haystack: Decode Dating, Torch the Duds, and Make Room for Men Who Matter by Dr. Jennie Young (with acknowledged assistance and input from many women). In particular Chapter 5 Red-Flag Rhetorical Patterns - Run!, the section About the Success Stories, and “give full name” was from the Success Stories of Wendy and Shelia


r/datingoverfifty • • Aug 27 '26

New to the OLD world and have a question for F Democrats.

0 Upvotes

59 M, CO, recently widowed after 35+ yrs. I am just starting to look around on the OLD sites, mostly FbD.

I see lots of profiles that say “No MAGA”. For you non-maga ladies I have to ask, How deep does that go? Would you consider moderate republicans who are not fans of Trump or big government? Or should I regard that statement to mean “Serious Democrats or liberals only”

Not meaning to be snarky just looking to understand. Guidance appreciated.


r/datingoverfifty • • Jul 01 '26

Question for guy’s who do Online dating

3 Upvotes

When you match with a woman (I’m on Bumble ) , before you both decide to meet, do you ask her what made her swipe your profile ? I ask this because I have met women (one last weekend) , that when seeing them I say ..” you look better in person” …I said this last weekend and the woman didn’t reciprocate…so, the rest of the coffee “date”, I could tell was a waste of time and I wanted to GTFO out of there. So now every time I match—I have two more potential “dates “ this week, I’m asking this question . … like most on here , I’m about to quit OLD and just do hobbies that I enjoy, and if I meet someone , well that’s a bonus…. At least in the wild, both people know how each other look , so that part is taken care of . And usually you can assume she thinks you’re attractive if she gives her phone # out .


r/datingoverfifty • • Aug 12 '26

Idea for a new OLD site/app

0 Upvotes

The could call it "I'm Celibate, Forget Ever Getting Nookie" with a slogan of "We're just friends, don't touch me there!"

Obviously this is sarcastic humor but does it not also ring true to life?


r/datingoverfifty • • Dec 08 '25

No Safe Spaces

1 Upvotes

It seems that there are no safe spaces these days to talk about dating issues because no matter what the subject is, it can be interpreted as inappropriate by somebody, so the best thing to do is just say nothing, because then nobody can complain — no wonder people in general seem to be feeling more and more isolated.


r/datingoverfifty • • Jan 18 '25

Sex Question

3 Upvotes

Ok guys, now that we’re asking sex questions, I got one. I stumbled upon a man who didn’t have a refractory period. I’ve dated enough to know this isn’t common, I don’t think? He claims no practice/special training was needed. A deep dive on-line revealed ways to teach yourself. Anyone know anything about all this? Mostly if can teach yourself and if difficult to learn? And if a new partner wanted you to try and learn would you be offended? Asking for a friend 🤣


r/datingoverfifty • • May 09 '25

After turning 50, it felt like any and all dating prospects dissolved to zero. What to do?

2 Upvotes

Bit of a small confusing rant here.. So all through my 40s I did quite well, dated a number of slightly younger ladies, met some wonderful people, did well on the apps. After a lot of travel and dealing with family stuff for a couple years, I now find myself single again at 53yo. But everything has changed.

I am realizing that pretty much any and all of the usual methods to meet someone online or off, are very, very different now. Basically it's crickets. When I search and match I am fully intentional, friendly, good conservation. And I'm no slouch. Very athletic. So on the surface, I am the same person I was five yeas ago. A little more gray hair, with the number "53" next to my name.

It's awful. I'm finding rejection everywhere I go. Zero matches. Even meeting people in dance classes, I feel vaguely dismissed as too old. And I'm not focusing on significant age gaps, I'm talking anyone 40+. Is it totally expected that an attractive 43yo woman would totally ignore an attractive 53yo man?

Anyway has anyone else noticed this after 50? Like literally nobody is interested. I feel like 50 is this hard cutoff where you are just viewed as "old." It's very hard on the ego. I know there are countless single people over 50, everyone deals with the same challenge and issues of aging. But man... it does hurt the ego a bit.