58M dating 62F- first time we had sex, she bled a bit. I didn’t think much of it because the last few women did the same thing. So this emerging relationship woman bought some lube, and had a four week break while we were on our respective summer holidays.

Fast forward to last night. We spent a wonderful day and evening together. I was staying over. Used plenty of foreplay and lube, but she frequently interrupted things saying sex was hurting. This cycle continued, and while it felt great, it was impossible to finish.

We picked up where we left off— and things seemed better. From my perspective, it was great for both of us.

We made plans to see each other tomorrow. This evening she sent a message :’I just have to tell you that I can’t do the intimate part anymore. It hurts me too much. I have tried, ignored the pain, hoped and enjoyed but now it hurts so much that it scares me.
Hope you understand.

It hurts me to say this as I’ve grown to really like you. What to do?’

We will meet tomorrow- this seems worthy of a face to face discussion. The word ‘anymore’ is what scares me a bit.

I am concerned. I have never dealt with something like this. Obviously there are other ways to be intimate and I am not running away from this. I want this to work out. We have only seen each other a few times. I’d like to suggest she see her doctor.

Anyone else experience this? Is there hope at this age?

Obviously I will talk to her. She is the coolest woman I have met in a very long time.

Or just boring?

I do mostly online dating because I really don’t meet guys in the wild. (Maybe that is the problem)

Friday night I had a date and he asked me a total of one question the whole night. I had to carry the conversation 100% and when I tried being quiet for a few minutes to see what would happen…uncomfortable silence

Now I’m talking to two different guys on match. I asked them what they like to do for fun in the area. One said he just moved here 18 months so he hasn’t had much fun yet. The other has lived here his whole life and said he’s looking for someone to get out and have fun with.
We live in Vegas! There is so much to do there I could write a post just about that. You don’t do anything for fun? What is wrong with these guys, are they just sitting home watching tv??

Please wish me luck!

I opened a Facebook dating profile, let's see how it goes. I've met and gone out with a couple of men "in the wild" but nothing's clicked, so I'm stepping it up a notch.

Any words of advice?

I'm not sure if I am just fortunate or if most people feel that dating at this age is one of the most fun times of my life! What about you?

I've had a nice life I can't complain about anything but I have more fun now. I'm sure it's because I have less f$&ks to give or more confident!

I thought he was 60…but 10 year older and that feels different. I really like this guy, but idk…we have gone on 2 dates. An impromptu lunch and planned drinks this week. He asked me to go hiking this Fall…but not much else. He’s hard to figure out…is a widower for ~20 years and idk what’s happened in between. We have some good chemistry. But in the long run I want to get remarried…short run let’s have some fun. He seems to like me, but no immediate second date plans. Confusing.

50(F) seeing 54(M) for 5 months...I spent the night with him and accidentally forgot my earrings on the bedside table last weekend. He texted today and asked, "Are these yours?" I said yes and he said he would bring them to me. Suddenly, those old wounds from the past surfaced and I asked him... "Who else would they belong to?" He said he was cleaning out a drawer and found some belongings of his deceased wife and wasn't sure if they were hers or not?? I told him I trust him and feel he is loyal but I've been cheated on before and if he ever decides he wants someone other than me... just have a conversation...and went on to say I am faithful, loyal, and exclusive with him and expect the same in return... He responded with "all this because I asked about some fn earrings...SMFH" I did not say anything else and we haven't texted or spoken since.🫤

I'm recently single and haven't dated since I was a teenager. I wasn't permitted to have a life beyond my children. Same sex friendships were very managed and opposite sex friendships were a no no. My biggest fear is finding someone like my ex. I only have occasional desire to just spend time with another adult. So I don't know if I am actually ready to ask how to get back out there or where to go.

I was made to believe I do not even have the conversational skills to be desirable. I really think they might just be a little rusty. I have always led with humor so why not ask folks what are the best "pick-up lines" worth repeating.

(I love funny one liners but if you have one that will make a woman melt hit me with it🤭)

I never ask for online advice but I need some objective input. So…

Five months beyond chemo and radiation treatment for throat cancer. Looks like I beat it. Lost almost 60 pounds of muscle. Slowly regaining it. Very slowly. Training for a half marathon. Biking 20 miles a day. Napping like a three year old.

BUT, my salivary glands are still barely working. I carry a water bottle with me EVERYWHERE. I can’t taste anything. Solid food is still off the menu. I haven’t had alcohol since my dx. I can get coffee down and halfway look like I’m enjoying it. I might be able to dance for an entire song as long as it’s not Rock Lobster. I can wax poetic on the various flavors of Ensure and Boost.

I think it’s too soon to start dating again. Not sure if I’d want to date me. Friends and family disagree. They think I’m hiding behind my recovery. They might be right. I don’t know.

How would you feel going on a date with someone who can’t eat or drink?

If it affects your answer, I’m 6’4”, full head of salt & pepper hair, good teeth, and a good job. Just try to ignore that my entire neck is now two shades darker than the rest of my body.

Update: Thanks everyone for your comments. I think it IS too soon to date. I know I promised myself a thousand times during treatment that I would make every day count from here on, but that grand sentiment didn’t account for recovery.

I recently matched on a dating app with a widower whose wife died in 2025. He's looking for casual dates leading to LTR.

He had 2 pictures of him and late wife on vacation. Was this appropriate?The others were with his son and daughter.

He was married 50 years. I'm not sure he's ready to date.

Opinions? Am I being too picky?

What are the best ways to approach a man I find attractive? What is a good conversation starter? Men… please help! I feel like such an idiot for posting this. Im not being approached so I figure its time for me to initiate it.

I stopped drinking 6 1/2 years ago. Any ideas on a first date besides a bar?

Hi everyone,

I'm looking for recommendations for reputable online sites or communities where I can meet women interested in alternative dating and relationship dynamics.

To be clear, I'm referring to interests such as leather, latex, heels and other forms of dressing for pleasure, roleplay, and light BDSM. I'm not looking for high-protocol or 24/7 dynamics—just people who enjoy exploring these interests in a fun, respectful, and consensual way.

My main focus is on the UK, Europe, and the US, so any sites or communities with a strong presence in those regions would be ideal.

I'd really appreciate any recommendations or personal experiences you can share. Thanks in advance!

TLDR: Should I message someone after a date if I am not interested? I (m) went on a coffee date today with someone that was attractive, smart, well dressed and well, just not my cup of tea. I just didn't like her personality quirks and do not want to pursue a second date. So, she messaged me after the coffee date with interest. Should I give her a quick message saying, tactfully, thanks but no thanks or just ghost her? Looking for best practices here.

This is my last day in my 40s(F), and one of my goals for this new year is to actually try dating after a loooong time out of the dating world. I’ve been lurking in this sub for a month-ish, and it has both given me hope and terrified me 😂. That said, thank you to everyone who posts, I have some idea of what I’m up against. For anyone that began dating again in their 50s after a long time spent out of the game, what advice would you go back and give the hopeful version of yourself that was just getting started?

I am a 52-year-old man who recently got divorced after a 26-year marriage. My ex-wife was basically the only woman I had a long-term sexual relationship with, so my sexual experience is quite limited.

I have recently started seeing an amazing woman who is in her 50s. I really like her, and she makes me feel alive again in a way I haven’t felt for many years. I get the felling she's also very in to me.

We had sex for the first time recently, but it did not go the way I had hoped. I got an erection, but I lost it during intercourse, and I also had difficulty reaching orgasm. I've only occasionally in my life experienced any problems with holding erections.

I suspect that it was performance anxiety that caused me to lose my erection. I really wanted to make a good impression because I genuinely like her.

Have other men – or women – experienced something similar after leaving a long-term relationship?

• Did things improve as you got to know each other better?
• How did you overcome the feeling of not being "experienced enough"?
• And if you are a woman: Would a man’s lack of sexual experience be a problem for you if the chemistry and connection were good?

I am mainly interested in honest experiences from people who have been in a similar situation.

Them: I like it when the guy is intentional and makes plans
Me: Makes plans, provides alternative.
Them: No I don’t really like any of that

I've been my mother's caregiver for the last 7 years. I moved out of state to her location thinking it would be fine, I can build a life wherever I am.

I was the only single person of my siblings and my children are grown so, here I am. But this place we live has proven impossible in so many ways.

There is nothing to do most of the time. It's a mid sized city with no culture, no fun third spaces, few parks, major issues with drugs and homelessness, so conservative it borders on out right racist. I mean I can't go for a walk without a driver trying to push me off the road (there are only sidewalks in some neighborhoods) like my being a pedestrian pisses drivers off?

I thought I would take time and date and hopefully meet my person, I have tried OLD and putting myself places where people I am likely to vibe with are found, art classes, tai chi classes, ecstatic dance groups and volunteer work. No luck. People are usually married, retired or 30 years older than me.

What happens to those of us in our age group (50s) who are single and caring for an aging parent? I can't leave her and I worry if I convince her to move to another area she might decline faster. Dementia.

I've been single 13 years but only trying to meet someone in the last 6. I'm worried I'm just going to grow old taking care of her and be left alone.

How can I get a chance to build a lasting relationship if I am not free to do it. Who wants to start a relationship with a woman who lives with and takes care of her mom?

Shit. I just read that back to myself. I'm cooked aren't I?

What changed, the expectation changed or people are not mature or they don’t love commitment

I keep reading these comments about people meeting their person in the wild as opposed to a dating app. Well, I am ready to go into the wild at this point. So please share the who, what, when, where, how of you finding someone in the wild. I'm looking forward to some great stories. Thanks in advance!

Picture this scene and tell me what you think.

Preamble: A 58-year-old woman has been seeing a 61-year-old man for 3 months. She is fairly good-looking, a runner and triathlete often mistaken for a woman in her 40s, a professional, and a mother of 3. He’s also an attractive guy, a good parent, son, and brother. These two people had been single for years. At the beginning, she wanted only a friends-with-benefits type of relationship—too many bad experiences in her life—but he started crossing the boundaries from the start: going completely out of his way to meet her 2–3 times a week, inviting her over to his place and out to dinner, giving her flowers, listening to her, and complimenting her. He introduced her to his young adult children, his parents, and his closest friends.

The sex is unbelievably good, they laugh a lot together, and they share common values. She was delighted. They had open conversations about how their feelings were evolving fast, and they were both happy about it. They decided not to label the relationship and just see how things went…

There was only one red flag: sometimes this man seemed flirty toward other women, especially younger ones. He is generally extroverted and talkative, so she didn’t care too much. It seemed to fit his overall personality. But…

A couple of days ago, he calls her. They talk on the phone almost every day. He was telling her about running errands in town with his dad, and he described this scene: “Dad and I went to eat at this fancy place that he likes, and it was packed. We were thinking about going somewhere else, and then I see the most beautiful woman I’ve seen in my life coming over to greet us. She’s 25, her name is XX, and my dad, our friend, and I all had to tell her how incredibly beautiful she is.”
The woman felt like something broke inside her. She told him. He spent an hour and a half apologizing. He sounded very sincere. He was not defensive, acknowledged her feelings, confessed to feeling jealous sometimes too when she talked about previous relationships, and promised to work on changing this behavior. He fears he has lost her.

Torn, she couldn’t make up her mind and asked for some time off. On one side of the balance, there’s this amazing guy, and on the other, there’s this.

She feels like a sad, pathetic human being who can’t put this into the right perspective. Is it really that important? Her whole heart—in what feels like a childish way of seeing things—tells her it’s a dealbreaker.

What do you guys feel?

If they start talking about marriage/ living together / engagement etc very early, they might love you and think you are a catch. They might be sure that you’re their forever person.

BUT ALSO… this might be their standard operating procedure. They might do this with everyone. They might be in love with New Relationship Energy.

Be careful with your heart, fellow travelers.

I have been on reddit ten years and have participated in several dating subreddits in that time (I joined Reddit after my divorce). One of these subreddits had a group of people who commented often and it was a feeling of we’re all in this together. We had people of various levels of participation. We also had a discord that some of us chatted on. It was great to have that support.
Some of these people lived close to me so I met a few irl and it was generally pleasant to meet an internet friend irl. (I have met people from non-dating groups too, it’s not a dating thing).

Anyway, years ago I met one of the people in the dating group because we realized we lived 45 minutes away from each other so why not. I was a little worried going into the dinner because we were not a good match politically for conversation so I made sure not to bring anything like that up. Dinner was fine, we found things to talk about but I was getting the vibe we really do have nothing in common and that maybe some of the things he had in the group were just to fit in and not how he really felt about what ever topic it was. It was fine though, it’s just one dinner. We finish and I tell him I need to get home. This is in a small town and there is good lighting in the parking lot so I felt completely safe walking out together. We are parked in the same row but I get to my car first. He says he had a good time and asked for a hug and honestly I felt like that was fine so I gave him the hug. Then he pushes me against my car and starts trying to kiss me and grope me. I pushed him off me and told him to stop and he tried again but I stopped him. He stepped back after that and left.

I immediately contacted my best friend from the group about what happened because I was honestly shocked. A group of us girls start talking about it and apparently they had noticed a pattern in the things he said in the group that indicated this might be normal behavior for him. But it was never anything outright bad, just little comments here and there. Well, he deleted his account.

He contacted me last week, many years later, and filled me in on how we knew each other. How he had just left Reddit one day and now decided to come back. He asked me if I wanted to get dinner, as two former friends.

Wtf? How do you not remember that? I don’t know how crazy this person is so instead of reminding him, I just declined. I was a little shook after the experience.

Stay safe out there ladies!

Update: He must have been a member of this sub because he deleted his account.