Slim picking dating in your fifties

Anonymous
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:Only losers men in their 20s and 30s sleep with older women in their 40s and 50s. A woman is like a car with 250K mileage on it. It does not matter how well you maintain it, it still has many issues. I have a vintage 1993 Lexus with 250K miles on it, and a 2025 Lexus with 2K on it. The 1993 Lexus has shown its usage despite that it is very well maintained, while the 2025 is practically "brand new". It is absolutely delusional to say that Kathy Ireland is more beautiful at 50 than she was at 22.

Successful and good-looking men, regardless of age, want to sleep with younger women because they have options. Losers men that don't have options have to settle for older women.

ok. so women are cars. men are equines. my dh is a stallion...you are a jackass.


Trigger much? I will say it again, successful and good-looking men want to sleep with younger women because they have options. Leonardo Dicaprio and many famous musicians are prime examples. It is just a fact of life.



You’re missing important motivators. Women in their 40s or 50’s who are still beautiful have money. Simply put it takes time and money to be beautiful as we age.

I don’t want their babies, or their ring. I don’t want to move in w them and they sure aren’t moving into my house. “Younger” women come with needs and wants. I just come wanting them


This is so delusional. a 50 years old used up woman is nowhere near her peak beauty of the age of 22. No man is going to pay full price for a 50 years old woman, except simps or losers.


I'm a woman and I agree. Maybe not "used up" as you so eloquently put it, but menopause is such a savage beast. Not to mention gravity!


But this assumes every man in that age group has a choice to be with someone in their 20s or 30s and it’s simply not true. Everyone brings up Leo DiCaprio, but statistically, most people who couple up in America are within a three year age range of each other. The next most common group are within about a five year age range of each other….beyond that it starts getting pretty small. less than one percent of couples in America have a 20 year or more age gap.

But also, people are not always looking for just sexual relationships. if you’re looking to date and just have sex, sure, but if you are looking for a real relationship, some people are staying married to the people that they partnered up with when they were younger and raised a family with or if they do divorce, looking for someone they have more in common with, who maybe can retire with them and travel together, etc. and certainly who is done wanting babies. You gotta love the delusional thinking that there are a bunch of 20 something women who don’t want their own kids but are totes fine having your brats around 50% of the time and dealing with your ex-wife. The young woman who don’t want kids are coupling up with men their own age and doing the DINK thing.

To act like every young woman is lining up a 50-year-old divorced dad it’s just not dealing with reality.


This was in reference to 50 something women dating younger men. If an attractive interesting 34 yo man is choosing a 53 yo woman over a 32 yo woman, that 53 yo woman better have a lot to offer (and it assumes the man doesn't want a family eventually). Those men are pretty rare.
Anonymous
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:"I’m not self centered I’m just being realistic in my dating: it’s impossible to find one man who would check all my boxes physically and emotionally. It is possible for a good looking and sexual 40s woman to date two 50s men, so that each would be meeting her specific needs. I’m just maximizing pleasure from what being single allows me at my age, and enjoying life to the max."

Why is it impossible? Are you actually looking for one man who checks all of your boxes? Or are you happier with simultaneous somewhat casual but somewhat serious relationships with multiple men? There are some women (and men) who are so uncomfortable with the thought of being alone that they always have more than one partner, or at least a backup plan. You sound like you might be one of those. I'm not criticizing. Just observing. I'm middled aged and I've been there.


Because I need both sex and sophistication. One partner is a sexual beast but we are not great exploring things outside bedroom. The other man is artistic, deep, we enjoy the same things but he’s too gentle in bedroom. And refuses to do or learn what I need sexually. I’m not scared of being alone it’s very easy for me to meet men it’s just I can’t find everything I need in one person


DP. Btw, you just said you are not scared to be alone because it’s easy for you not to be alone.


There is no need for me to be alone. I enjoy sex and company of both of them. Yes I have sexual needs and prefer them met in partnered sex if I can find safe longer term partners. I can still date others. Last year I was busy with other stuff in my life and was single. Not sure what’s your problem.
Anonymous
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:"I’m not self centered I’m just being realistic in my dating: it’s impossible to find one man who would check all my boxes physically and emotionally. It is possible for a good looking and sexual 40s woman to date two 50s men, so that each would be meeting her specific needs. I’m just maximizing pleasure from what being single allows me at my age, and enjoying life to the max."

Why is it impossible? Are you actually looking for one man who checks all of your boxes? Or are you happier with simultaneous somewhat casual but somewhat serious relationships with multiple men? There are some women (and men) who are so uncomfortable with the thought of being alone that they always have more than one partner, or at least a backup plan. You sound like you might be one of those. I'm not criticizing. Just observing. I'm middled aged and I've been there.


Because I need both sex and sophistication. One partner is a sexual beast but we are not great exploring things outside bedroom. The other man is artistic, deep, we enjoy the same things but he’s too gentle in bedroom. And refuses to do or learn what I need sexually. I’m not scared of being alone it’s very easy for me to meet men it’s just I can’t find everything I need in one person


DP. Btw, you just said you are not scared to be alone because it’s easy for you not to be alone.


There is no need for me to be alone. I enjoy sex and company of both of them. Yes I have sexual needs and prefer them met in partnered sex if I can find safe longer term partners. I can still date others. Last year I was busy with other stuff in my life and was single. Not sure what’s your problem.


That’s funny. I have no problems. I just find it humorous how you don’t even see that you keep making PP’s point.
Anonymous
[list]
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:"I’m not self centered I’m just being realistic in my dating: it’s impossible to find one man who would check all my boxes physically and emotionally. It is possible for a good looking and sexual 40s woman to date two 50s men, so that each would be meeting her specific needs. I’m just maximizing pleasure from what being single allows me at my age, and enjoying life to the max."

Why is it impossible? Are you actually looking for one man who checks all of your boxes? Or are you happier with simultaneous somewhat casual but somewhat serious relationships with multiple men? There are some women (and men) who are so uncomfortable with the thought of being alone that they always have more than one partner, or at least a backup plan. You sound like you might be one of those. I'm not criticizing. Just observing. I'm middled aged and I've been there.


Because I need both sex and sophistication. One partner is a sexual beast but we are not great exploring things outside bedroom. The other man is artistic, deep, we enjoy the same things but he’s too gentle in bedroom. And refuses to do or learn what I need sexually. I’m not scared of being alone it’s very easy for me to meet men it’s just I can’t find everything I need in one person


DP. Btw, you just said you are not scared to be alone because it’s easy for you not to be alone.


There is no need for me to be alone. I enjoy sex and company of both of them. Yes I have sexual needs and prefer them met in partnered sex if I can find safe longer term partners. I can still date others. Last year I was busy with other stuff in my life and was single. Not sure what’s your problem.


That’s funny. I have no problems. I just find it humorous how you don’t even see that you keep making PP’s point.


The PP has no point they are just trying to equate “being social, needing physical sex and enjoying non- monogamous lifestyle” with “scared to be alone”.
Anonymous
I'm the PP. I know a woman who lives her life like the woman who's been sharing some details of her life here. That other woman says many of the same things. That other woman is also scared to be alone. I don't know the woman here. Also, being alone is scary to me so I wouldn't criticize the woman here for finding it scary.

I do wonder whether the woman here actually would be happier if she found one man who checked all her boxes, or whether that would just make her anxious. Again, I don't know her and I don't know much about how she feels and thinks. I'm not criticizing.
Anonymous
A beautiful 50's woman might be prettier than other 50's women, but she is nowhere near a 20's woman in terms of beauty. I was one of the best D1 tennis players at UCLA in 2001, and in 2025, I would be embarrassed on the tennis court by the worst player on the UCLA men's tennis roster.

Any guy with options will choose a 20's over a 50's woman. Leo DiCaprio or John Mayer can do that because they have money and talents. That translates into options. The vast majority of men and women choose people around their age because they have very limited options.
Anonymous
Anonymous wrote:A beautiful 50's woman might be prettier than other 50's women, but she is nowhere near a 20's woman in terms of beauty. I was one of the best D1 tennis players at UCLA in 2001, and in 2025, I would be embarrassed on the tennis court by the worst player on the UCLA men's tennis roster.

Any guy with options will choose a 20's over a 50's woman. Leo DiCaprio or John Mayer can do that because they have money and talents. That translates into options. The vast majority of men and women choose people around their age because they have very limited options.


We’re not tennis players or cars or just our age.
Anonymous
Anonymous wrote:A beautiful 50's woman might be prettier than other 50's women, but she is nowhere near a 20's woman in terms of beauty. I was one of the best D1 tennis players at UCLA in 2001, and in 2025, I would be embarrassed on the tennis court by the worst player on the UCLA men's tennis roster.

Any guy with options will choose a 20's over a 50's woman. Leo DiCaprio or John Mayer can do that because they have money and talents. That translates into options. The vast majority of men and women choose people around their age because they have very limited options.


Even Elon Musks options are limited. He fornicated with a not very attractive twenty something single mother of a toddler. A famous and gorgeous 20s model didn’t pick him. The last gorgeous woman he dated was Amber Heard and there are only 12 years apart
Anonymous
Anonymous wrote:
Anonymous wrote:A beautiful 50's woman might be prettier than other 50's women, but she is nowhere near a 20's woman in terms of beauty. I was one of the best D1 tennis players at UCLA in 2001, and in 2025, I would be embarrassed on the tennis court by the worst player on the UCLA men's tennis roster.

Any guy with options will choose a 20's over a 50's woman. Leo DiCaprio or John Mayer can do that because they have money and talents. That translates into options. The vast majority of men and women choose people around their age because they have very limited options.


Even Elon Musks options are limited. He fornicated with a not very attractive twenty something single mother of a toddler. A famous and gorgeous 20s model didn’t pick him. The last gorgeous woman he dated was Amber Heard and there are only 12 years apart


99.999% of women would pick John Mayer over Elon Musk.
Anonymous
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:A beautiful 50's woman might be prettier than other 50's women, but she is nowhere near a 20's woman in terms of beauty. I was one of the best D1 tennis players at UCLA in 2001, and in 2025, I would be embarrassed on the tennis court by the worst player on the UCLA men's tennis roster.

Any guy with options will choose a 20's over a 50's woman. Leo DiCaprio or John Mayer can do that because they have money and talents. That translates into options. The vast majority of men and women choose people around their age because they have very limited options.


Even Elon Musks options are limited. He fornicated with a not very attractive twenty something single mother of a toddler. A famous and gorgeous 20s model didn’t pick him. The last gorgeous woman he dated was Amber Heard and there are only 12 years apart


99.999% of women would pick John Mayer over Elon Musk.


I mean if they had a gun to their head. The vast majority would pass on both.
Anonymous
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:I was at a higher end club tonight geared to the 30+ crowd. Most of the men dress OK at best, but not well. Maybe 2-3 men wearing blazers for example.

I dress well and I had women coming up to me. They were all in their 40's and 50's. We had fun dancing then I called it a night, but the tables are turned from when I was in my 20s!


At 55—ugh that club sounds awful to me. Give me a bar and an ice cold martini—but an actual club dancing…yuck


We know the average DCUMer is not the adventurous type. Black Cat in DC has 80's night every couple months (next is on 8/2) and it's one of the best crowds I've encountered. Everyone there is 30+ given the music, and they _want_ to be there, so it's people who like music and don't mind dancing. Everyone is polite too -- no shoving or jumping the line to get a drink, since we're all old enough to be over that nonsense!


30 and 55-60 is very different. Lmaof. I have kids and nephews in their early 30s. When I was 30 I wouldn’t be caught dead partying with the yacht club crowd.
Anonymous
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:A beautiful 50's woman might be prettier than other 50's women, but she is nowhere near a 20's woman in terms of beauty. I was one of the best D1 tennis players at UCLA in 2001, and in 2025, I would be embarrassed on the tennis court by the worst player on the UCLA men's tennis roster.

Any guy with options will choose a 20's over a 50's woman. Leo DiCaprio or John Mayer can do that because they have money and talents. That translates into options. The vast majority of men and women choose people around their age because they have very limited options.


Even Elon Musks options are limited. He fornicated with a not very attractive twenty something single mother of a toddler. A famous and gorgeous 20s model didn’t pick him. The last gorgeous woman he dated was Amber Heard and there are only 12 years apart


99.999% of women would pick John Mayer over Elon Musk.


I mean if they had a gun to their head. The vast majority would pass on both.


Agree, as a woman I dated 20s and 30s in my 20s. 40-50s men looked ANCIENT to me regardless of their accomplishments or looks
Anonymous
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:A beautiful 50's woman might be prettier than other 50's women, but she is nowhere near a 20's woman in terms of beauty. I was one of the best D1 tennis players at UCLA in 2001, and in 2025, I would be embarrassed on the tennis court by the worst player on the UCLA men's tennis roster.

Any guy with options will choose a 20's over a 50's woman. Leo DiCaprio or John Mayer can do that because they have money and talents. That translates into options. The vast majority of men and women choose people around their age because they have very limited options.


Even Elon Musks options are limited. He fornicated with a not very attractive twenty something single mother of a toddler. A famous and gorgeous 20s model didn’t pick him. The last gorgeous woman he dated was Amber Heard and there are only 12 years apart


99.999% of women would pick John Mayer over Elon Musk.


I mean if they had a gun to their head. The vast majority would pass on both.


The last time I went to a John Mayer's concert, the line of women waiting to bone him was very long.
Anonymous
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:A beautiful 50's woman might be prettier than other 50's women, but she is nowhere near a 20's woman in terms of beauty. I was one of the best D1 tennis players at UCLA in 2001, and in 2025, I would be embarrassed on the tennis court by the worst player on the UCLA men's tennis roster.

Any guy with options will choose a 20's over a 50's woman. Leo DiCaprio or John Mayer can do that because they have money and talents. That translates into options. The vast majority of men and women choose people around their age because they have very limited options.


Even Elon Musks options are limited. He fornicated with a not very attractive twenty something single mother of a toddler. A famous and gorgeous 20s model didn’t pick him. The last gorgeous woman he dated was Amber Heard and there are only 12 years apart


99.999% of women would pick John Mayer over Elon Musk.


I mean if they had a gun to their head. The vast majority would pass on both.


The last time I went to a John Mayer's concert, the line of women waiting to bone him was very long.


And? Star bangers still line up for Mick Jagger.
Anonymous
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:
Anonymous wrote:A beautiful 50's woman might be prettier than other 50's women, but she is nowhere near a 20's woman in terms of beauty. I was one of the best D1 tennis players at UCLA in 2001, and in 2025, I would be embarrassed on the tennis court by the worst player on the UCLA men's tennis roster.

Any guy with options will choose a 20's over a 50's woman. Leo DiCaprio or John Mayer can do that because they have money and talents. That translates into options. The vast majority of men and women choose people around their age because they have very limited options.


Even Elon Musks options are limited. He fornicated with a not very attractive twenty something single mother of a toddler. A famous and gorgeous 20s model didn’t pick him. The last gorgeous woman he dated was Amber Heard and there are only 12 years apart


99.999% of women would pick John Mayer over Elon Musk.


I mean if they had a gun to their head. The vast majority would pass on both.


The last time I went to a John Mayer's concert, the line of women waiting to bone him was very long.


Because he’s rich which proves the prior point. 20s women would only sleep with much older men if they can offer something material: fame, money career opportunities etc
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