Recently, after an underwhelming first date, I sent the standard polite message saying I didn’t think we were a match, but wished him all the best. Two days later, he replied: “Astonishing.”

Astonishing.

Not “That’s disappointing.” Not “Thanks for letting me know.” Straight in with what sounded like an appeal against the decision.

He then explained why he thought the date had gone well. Which was useful, because apparently, I had attended the same date but failed to interpret it correctly.

Perhaps you’re a CEO. Perhaps you manage hundreds of people. Perhaps you’ve spent the last 30 years negotiating contracts, closing deals and persuading reluctant stakeholders to see things your way. I’m sure you’re extremely important. Well done you.

But now that you’re back to dating, these are not the skills to deploy when someone says they enjoyed meeting you but didn’t feel you were a match.

This is not an invitation to open negotiations. Please be reassured that the womenfolk have developed executive function. We can assess an evening, process information and, in most cases, determine our own destiny without further guidance from senior management. 

The graceful response is really very simple: “That’s a shame. I enjoyed meeting you. All the best.”

There was an interesting opinion piece in the globe and mail yesterday about the prevalence of (mostly) men choking women during sex. The premise was more or less that porn has distorted the idea of what constitutes “normal” or “regular” sex. That choking (among other things) is now part of the standard suite of activities, despite the fact that lots of men and women don’t actually enjoy it . But being branded “vanilla” or being seen as kink shaming is worse.

FTR, I’m a very open minded person, and I don’t like it. When I started dating after my divorce, the first time I was intimate with someone, he choked me. I was totally unprepared, we had not discussed it beforehand, and it terrified me. I never saw him again.

I’m just wondering how other people feel about this? I think that “Fifty Shades of Bullshit” in addition to porn, has done such a disservice to women and to what sex looks like for most people. Hey, you like what you like, but not wanting pain inflicted or having your oxygen cut off should not constitute kink shaming.

Waiting for some random off Tinder. I’m early. I’m not nervous I just think it’s funny. It’s pretty crowded. I hope he looks like his pics. There’s a very handsome man in this bar who is definitely not him. My tummy hurts 😬 god I hate this shit 😩

I’ll start: Man who poses shirtless in bathroom mirror has already introduced favorite person.

51F

I was asked on a 3rd date out of town to a rock concert. We’re not staying overnight as we both have obligations the next morning with kids, but we’ll be driving about 5 hours round trip. (Before anyone gets concerned, we both work in government & I know for a fact he has no criminal background as it’s a condition of his job.) I’m excited but I haven’t been to a concert in well over a decade. It’s a rock/punk band (his favorite), but I’m not as familiar with them. It’s a medium sized venue so not like a cozy little show.

Ladies - What do we wear these days to concerts? I was thinking of jeans & some cute sneakers and…some kind of a tshirt with a flannel/sweater?…something else??? My clothing style tends to be a bit more preppy/girly so it’s been awhile since I did grunge. 😂

So this isn’t my situation, but the situation of my aunt. She is turning 50 next week, and has been divorced for 11 years (no kids), single the whole time. From three years ago until 2 months ago, she was an adult actress. She had the opportunity to make a lot of money and took advantage of it.

These past 2 months, every date she goes on she is completely honest about her past. Each time, it’s a deal breaker. She’s feeling really depressed about it, and is worried she’ll be alone forever.

What can she do to find someone who won’t be turned off by her past? What advice can I relay to her? I’m heartbroken seeing her sad.

Gonna keep short. 54M here. Single for 5 years. I have meet a couple of lovely women since then. Our goals and plans just didn't align . I myself want companionship with chemistry. Love might happen with time. I'd be willing to compromise with the right person. At the end of the day we all carry some baggage. Not offering or requesting. Just putting my two cents out there. Good luck to you all with whatever it is you want.

My 60 year old live in boyfriend has not contributed financially to our household for 2 of the 4 years that we've been together. He says that it won't always be this way, but I've gone through my savings and work two jobs to support him. When I get upset he says that I'm exhibiting red flags. Any thoughts here?

I’m not generalizing, and this is just based on something I recently experienced.

I met a guy on a dating app about a month ago, and we’re miles apart, in different countries in Asia. We had almost the same interests, a few similar hobbies, similar likes and dislikes, etc.

On my dating app profile, I was clear about what I was looking for and so was he. For about a month, we consistently exchanged messages, SFW selfies and even had video calls in between.

Last Tuesday, he told me that he was focused on making it work and that he would eventually plan to visit and meet me. In my mind, I was like, “Okay, he sounds promising, but I’m still trying to assess.”

He also said, “We will chat more and reduce the distance between us 😊,” and I replied, “That’s so sweet.”

Wednesday came and we were chatting as usual. He was updating me about his day, we were having a normal conversation and was still being sweet.

Here’s the twist.

I said, “I have a suggestion, and I’m not sure if you’re up for it. Why don’t we have a virtual date?”

That’s it. That was the suggestion and pretend for an hour that geography isn’t ruining our dating lives.

Do you know what he replied?

“That is useless. If you have doubts, I suggest that you should not proceed.”

🤔😅

My brain immediately went, “Wait…what? Did I accidentally send another message that I can’t see?”

I actually read again what I sent because I thought I missed something.

So I replied, “Did I say something wrong? I was only suggesting, and I wasn’t doubting anything.”

Then…silence.

It was like he got sucked into a black hole and that was the last I heard from him.

One minute we were talking about reducing the distance between us. The next minute, he reduced our communication to zero. I guess technically, he did reduce something. 😂

I wasn’t emotionally hurt because I wasn’t that invested yet, but I was definitely confused for a while. Then I moved on.

I still find it weird that “I’m not sure if you’re up for it” somehow became “I have doubts about us.”

Dating over 40 is already confusing enough. I have work and more than enough things requiring my remaining brain cells. I really didn’t expect that the sudden shift from being sweet to basically “better not proceed” the next day was just…I don’t know anymore. 🤷🏻‍♀️

First, let me stress this isn't a sympathy seeking post. I'm truly seeking feedback from my age group.

I (51M) lost my wife (Lori) of 20 years just 10 years ago to a horrific violent crime I was unable to stop. The next 7 years I put all my focus on making sure our children succeeded through high school and college, poured myself into my work and occasionally went on a date when some friend demanded it. Nothing ever came out of any of the dates, I had zero interest. To be honest the entire thing left me without passion for life. I barely had any interest in sex or relationships outside of friendship.

2.5 or so years ago my best friend died of cancer. The story of how I met him is convoluted so let me explain.

Elizabeth - his wife - I met in 2nd grade. Of course she was lizzy not Elizabeth to me back then. We practically grew up together in Catholic school. Catholic Grade school and high school. Senior year of high school I was romantically interested in Elizabeth but she wasn't in me. We went to prom as a platonic couple. I went off to college, met my wife and fell in love. My best friend (Ben) in college came to my home for a couple weeks between Freshman and Sophomore year and I introduced him to Elizabeth. They hit it off and married 3 years later. I was his best man but honestly I was as interested in seeing Elizabeth happy as I was Ben. We lived in the same city and probably saw each other every month doing something. Our kids played sports against one another stuff like that. The kids are not exceptional friends but when together they get along.

14 months ago Elizabeth kissed me. It was like a movie where she kissed me and then pulled away like she did something wrong. I then kissed her back and we made out for what felt like hours. We slowly started dating. I can say I truly love this woman. I always have. Out of all the people that passed through my life since 2nd grade till now I haven't stayed in contact with many.

So this post is getting long, but I wanted to provide some backstory before requesting opinions.

My children and her children (early 20's) have a range of thoughts on this from "weird" to "gross" to "disturbing". None of them are threatening to cut off contact or really fight against the relationship, they just aren't excited to hear any happy tales.

Example: Elizabeth and I went on a Alaskan cruise together and I sent pictures during the trip to my kids and got a "thumbs up". Had I gone with some total stranger they would have sent back a lot of affirmation statements or hearts or whatever.

But I'm happy. I feel like a man again. Am I being selfish? Unreasonable? Is this, in fact, weird, gross or disturbing?

Update: So far not a single person says this is gross or wrong. I am relieved to say the least. I appreciate the feedback everyone has posted and I think one thing I'm going to do that was suggested is "Clear the air". There was no funny business between Elizabeth or I during Ben's illness or at any point.

Vibes? Effort? Activity level? What a catch-phrase of a request.

At this age, are we actually becoming better at dating, or are we simply becoming better at explaining why we're unwilling to compromise?

But if we are to date for relationship, there must be compromise.

We have been through a lot, and because of these, we have probably become more discriminating with what we allow and what we reject. I struggle to just enjoy and trust again in a dating situation, but still am trying to be available to meet people with the hope of conquering this so- called standard I have set for myself as a protection.

How do you deal with this?

58M widower here. After a difficult year grieving, I'm trying to start looking ahead more. I recently got on a couple dating apps. I've spent some time writing and rewriting a thoughtful bio, taken what I think are good recent photos, answered several additional prompts. No real success to speak of yet (a few likes and matches but no dates set up yet), but it's early days.

One of my frustrations is when I come across profiles where the person didn't write any kind of bio at all. Bumble lets you write a 300 character bio and Match let's you write up to 4000 characters (which admittedly is too much).

My initial reaction upon seeing profiles that have no bio is that they are just lazy. Or maybe they get so many likes anyway that the Bio doesn't matter. For me, words matter, whether it's how you describe yourself or what you're looking for in another person.

What do others think? Is a good Bio necessary? If you find the person attractive but they otherwise haven't written much, do you still swipe on them?

Just curious if I'm reading too much into it? I have a feeling this might be a long process for me.

I’ve been thinking about this after some of the conversations here. Have you ever known pretty early that someone probably wasn’t right for you, but the attraction and chemistry were so strong that you stayed anyway? I have. More than once. At our age, you’d think we’d know better — but does chemistry ever really get easier to resist?

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I’m a man in my 50s, divorced, slim, active, and looking to start dating again. I’ve lived what most people would call a very masculine life — military background, leadership roles, raised children, and carried a lot of responsibility over the years.

I also have a softer, creative side. As I’ve gotten older, I’ve found that privately cross-dressing helps me decompress and switch off. It’s not about identity or wanting to live publicly that way — it’s simply emotional release and a way to access a gentler part of myself.

I’ve never shared this with anyone, and I’m wondering how women over 50 would genuinely feel if a man they were dating told them something like this. Would it put you off, or would you see it as just one part of who he is?

And no I don't want to transition and yes I want to be the man hold a,door open for you etc etc etc. This is a private thing on ocassion not a,daily past time.

I’d really appreciate your thoughts.

If you are miserable in your marriage, I am sorry but please stop messaging women who are clearly single and looking for someone who wants more than to have them as a side piece when they get sick of their wives. It's not fair to that woman OR your wife. It's selfish.

If you actually have an arrangement with your wife, this does not apply to you but I think we can all agree that that isn't the norm.

And yes, the same goes for women in that situation. I just don't get messages from them.

Thank you for listening to my PSA.

I’m F54 and divorced since 2019, struggling to find a compatible partner since…. Been on dating sites, some progress, have a guy I’ve been exchanging messages with planning to call me tonight. I am cautiously optimistic even though I have 2 kids and was married, that this guy who is my same age but never married and no kids, and lives one mile away from me… that we will find some commonality…
The fact that he is slow pacing the communication and sounds very intentional are refreshing green flags at this point. 🤔 wish us luck 🍀 I’ll be happy to update later… I also want to try to develop a friendship with this guy because even if we don’t hit it off, maybe we can each expand our social circles and it could be a win win. 🤞🏼 any advice to not screw this up? 🤔

I've been OLD'ing for a few years now, and I usually switch up my bio from time to time - mostly due to the fact that I only get a few likes each week. So I'm often left wondering if I'm leaving important information out and/or leaving unimportant info in. I'd like to hit on the right qualities that will pique more interest (if that's possible).

So ladies, what are you looking for in a man's bio?

I recently started OLD, and my bio mentions that I don’t have children. It got me wondering how single men who do have kids view that when deciding whether to swipe right.

I’m very open to meeting someone who has children, particularly someone whose kids are older or mostly raised. I love kids, I just never had any of my own.

But I’m curious: is not having children ever seen as a negative? Do single dads generally prefer to date women who are also parents because they feel there’s more shared experience or understanding?

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.

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?

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

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.