Should I date a younger woman?

[Myasylum]

I'll be 50 shortly.  Been divorced for 3 years and children are grown. 

    I haven't dated anyone seriously since,  but I have to admit,  things are getting lonely. 

There is a new woman at work that I'm quite fond of,  and of course she's married,  but she told me she had a younger sister that was single.  I said,  "really??"

    Well that younger sister is 28 years old. That kind of through me for a loop... However I thought it doesn't hurt to meet her, so I did meet her with my co-worker.  I wouldn't say there was a love connection of any kind, she is obviously younger looking, but i just kind of let it go. It just felt odd.

    A week went by and my coworker ask if I have talked to her sister. I just said no... I'm just taking my time. So she ask if i wanted to go out again. After a brief thought.. I said sure? Why not? So now my coworker and her sister and I are going to be meeting up again next week.

    Now, my ex wife is 10 years younger than me, so I'm kind of use to it. I've always been told I look way younger than I am (both blessing and curse)... but? This girl is 22 years younger than me! I'm not so sure she realizes this either?!  My Co-worker did say that age didn't matter to her sister, but? 22 years doesnt matter?

    I'm being super patient with this, and I even think just being friends or having a girl to hang out with would be cool... yet. I'm hesitant... and finding myself pulling back. Maybe that's a good thing? Idk?

Any opinions or suggestions on the matter?

Thanks!

Edited September 14, 2020 by Myasylum

[ajequals]

Unfortunately I feel with your divorce. and the age difference you will not be able to relate to a younger man. It would be more of a relationship with your older children. you would want to be in control instead of it being a relationship. The only man that could relate and understand is a older man. this is even true when a older man want to date a younger woman. why does he do that?  He thinks he can train her in a  mold of what he wants. Basically control her. How does that even work?  it doesn't. I recently read such a story. the young girlfriend took you sugar daddy to meet her friends. they asked who's dad is that?  do you want to hear who's mom is that?

[Myasylum]

Well... I'm a dude,  not a woman.  I also have no interest in controlling anybody.  Not my thing. 

   Thanks for the input though. 

[CaliforniaGirl]

Well, I would say give it a shot because who knows, but it seems like you don't feel that romance connection, plus it feels weird. So it seems like there's no point, you know?

[ShyViolet]

It's not unheard of.  People definitely do this.  The question is, do you honestly think you'll have enough in common with a 28-year-old?  Does immaturity annoy you?  Would it bother you if you and her are at two very different life stages?  Or would you not care?  If you want to go for it, then go for it, why not.  Make sure she knows your age up front.  She might think you're younger than you actually are, and then when she finds out your age she might get a little freaked out.  You don't want to set yourself up for that.

[DarrenB]

Has your age actually been discussed to the younger sister?

 

[Caauug]

4 hours ago, Myasylum said:

A week went by and my coworker ask if I have talked to her sister. I just said no... I'm just taking my time. So she ask if i wanted to go out again. After a brief thought.. I said sure? Why not?

Why not date her? If Sis is in a big rush to get married and kick out a couple of kids, I can see you backing off..... You have been there and done that. But if the dating is only for companionship, fun times and free meals for her, why not? It will give you opportunity to sharpen your social skills lost in your marriage/divorce. 

Be careful of entrapment. 

[chillii]

4 hours ago, ajequals said:

Unfortunately I feel with your divorce. and the age difference you will not be able to relate to a younger man. It would be more of a relationship with your older children. you would want to be in control instead of it being a relationship. The only man that could relate and understand is a older man. this is even true when a older man want to date a younger woman. why does he do that?  He thinks he can train her in a  mold of what he wants. Basically control her. How does that even work?  it doesn't. I recently read such a story. the young girlfriend took you sugar daddy to meet her friends. they asked who's dad is that?  do you want to hear who's mom is that?

This controlling idea of yours could not be further from reality , very generalizing and extremely presumptuous. What you think when all these cougars go after young guys shes looking to control him , ummmm, l don't think that's quite what's on her mind, do you ?  And not to generalize myself but being a guy about the same age as op l don't even know a guy that would want to control her , most men love her as an equal to enjoy life with to contribute to life and the relationship . lf they do go chasing younger women which the op obviously isn't he doesn't even know whether to bother for obvious reasons , it's usually nothing to do with control.

And just for op well , it wouldn't be my thing other than for some very nice well hopefully, fun , which wouldn't be my thing anyway in that way could've 100 times but nope relationship wise as a whole is personally what interested me and for me , that wouldn't work . l needed somebody more at my stages and levels.

[d0nnivain]

The age doesn't bother me as much as the co-worker's continued involvement.  It's lovely that she introduced you to her sister but for her to be present during this 2nd meeting is awkward at best.   Get her the heck out of the middle of whatever is going on & then be very careful.  You need to assume that everything you do & say with the sister will be reported to the co-worker.  

[smackie9]

By the sounds of it, you are feeling pressured.....do what's comfortable for you. You have other options, like just date casually to get yourself out of the house on Friday nights.

[elaine567]

2 hours ago, d0nnivain said:

The age doesn't bother me as much as the co-worker's continued involvement.  It's lovely that she introduced you to her sister but for her to be present during this 2nd meeting is awkward at best.   Get her the heck out of the middle of whatever is going on & then be very careful.  You need to assume that everything you do & say with the sister will be reported to the co-worker.  

Yes it is a bit weird.

Unless this is a culture thing with a chaperone needed then my guess the coworker is likely more interested in dating you than the sister is, but as she is married it can't happen so she has set up this  arrangement where she gets to come out with you... Otherwise why not give you the sister's number and you could have set up your own dates...
I don't think the sister is that interested tbh and I guess neither are you.
It could get awkward at work if for instance down the line you dumped the sister..

[Ruby Slippers]

Make sure she knows how old you are, and find out where she stands on marriage and kids. If she wants that soon, are you game? The one big risk is that she'll eventually leave you because of the age difference. You read about that a lot on this forum when men date much younger women, and the guys always seem just destroyed. If all this aligns, you're interested, and you're OK with the risk, I see no reason not to go for it.

[Azincourt]

16 hours ago, Myasylum said:

I'll be 50 shortly.  Been divorced for 3 years and children are grown. 

    I haven't dated anyone seriously since,  but I have to admit,  things are getting lonely. 

There is a new woman at work that I'm quite fond of,  and of course she's married,  but she told me she had a younger sister that was single.  I said,  "really??"

    Well that younger sister is 28 years old. That kind of through me for a loop... However I thought it doesn't hurt to meet her, so I did meet her with my co-worker.  I wouldn't say there was a love connection of any kind, she is obviously younger looking, but i just kind of let it go. It just felt odd.

    A week went by and my coworker ask if I have talked to her sister. I just said no... I'm just taking my time. So she ask if i wanted to go out again. After a brief thought.. I said sure? Why not? So now my coworker and her sister and I are going to be meeting up again next week.

    Now, my ex wife is 10 years younger than me, so I'm kind of use to it. I've always been told I look way younger than I am (both blessing and curse)... but? This girl is 22 years younger than me! I'm not so sure she realizes this either?!  My Co-worker did say that age didn't matter to her sister, but? 22 years doesnt matter?

    I'm being super patient with this, and I even think just being friends or having a girl to hang out with would be cool... yet. I'm hesitant... and finding myself pulling back. Maybe that's a good thing? Idk?

Any opinions or suggestions on the matter?

Thanks!

Yeah... I wouldn't do that.

A woman who is in her 20s and interested in dating or marrying a man who is old enough to be her grandfather if the guy had become a dad early in life - she's usually interested in what he can do for her. Financially.  Besides that you shouldn't be calling a woman past the age of 18 ''girl,'' because that kinda demeans her, as she's an adult, but I'd really consider why you'd be interested in dating a woman who is your kids age or  close to it, other than the attractive body and face she possesses, certainly, but there's a lot more to a relationship than just wanting to have sex with a woman.

Unless you are only looking for sex, and she's only looking for a little help to pay the bills. In that case, it's fine. The economy needs stimulation anyway and college debt ain't pay itself.

Listen, I'm sure you look young for your age.

But there's being in your 30s and looking young enough for women who are 10 years younger  to actually be attracted to you because, you're well, physically attractive and you are youthful in appearance and behavior, and then there's I'm a 50 year old man interested in dating a woman who is barely out of college because.. I dunno , man. Everyone looks their age, more or less, and I don't know that many guys who are 50 and look 27. I mean, sure,  Tom Cruise and Brad Pitt can pull it off, to look like they're in their 30s.. but it's not like the average guy looks like how Brad Pitt and Tom Cruise started out, and it's not like the average guy can afford the plastic surgery Brad and Tom Can afford..Jesus Christ talk about a man's grasp exceeding his reach..

Edited September 14, 2020 by Azincourt

[SumGuy]

It seems like the older sister is trying to set you up...think hard no matter what road you take as you will be seeing this older sister at work.  If you somehow offend the older sister in all this could be awkward. 

[Azincourt]

Considering the rush the older sister is trying to set you guys up and to make you guys a couple, makes me wonder if older sister isn't in need of help $ and she's trying to get you addicted to her younger sister to get you to help out with the finances.

Or, the younger sister is in trouble, pregnant or has an history of having terrible boyfriends, and she's trying to get some emotional and financial stability in her sister's life.

[mark clemson]

My take would be -

IF you would hope for it to be LTR/potential wife or LT GF, then proceed very cautiously. It could end up great, but I think the expectation is it that it would be more of a fling/"fun" STR. You've been dating a while so perhaps you've "gotten that sort of thing out of your system." I would assume it wouldn't last due to your differences; possibly you'll be pleasantly surprised.

If you would be looking more for ST fling, etc, then yeah, just rock it with her and see where it goes. If she happens to turn into the next great love of your life, well that's wonderful, but I wouldn't go planning for that.

[Azincourt]

But why would a 27 year old be looking for a fling with a 50 year old man?

Are there no men her own age or a few year older where they live at?

Is there like a majority of older men and younger women living in their city, which means young women looking for flings have to do it with a much older man?

Those are the questions OP needs to ask to himself.

[SumGuy]

8 minutes ago, Azincourt said:

But why would a 27 year old be looking for a fling with a 50 year old man?

...

Experience, maturity, calm, he's proven himself via life in certain and various ways, she has heard about him from her older sister and likes what she hears and sees, it turns her on.  Know it's not common but as  50+ old guy myself not uncommon, and not just about being taken care of financially.   His financially stability may be attractive, not so much about giving her money but what is says about his character.

A 50 year old divorced guy could make the perfect fling partner, he wouldn't rush her into marriage or a relationship and may not make it more than she wants it to be yet not treat her like just an FWB, both ends of the spectrum 30 something guys would fall in to.   She may have just met one too many marry me tomorrow or you are just the flavor of the month 20-30 something guys.

Last but not least, not all 50 year old men are out of shape and lagging in "libido," the ones in good shape and high "libido" do more than fine.  

So many legitimate reasons she may prefer him in particular, pretty sure she would not go for just any 50 year old.  The information from her sister is likely key.

[Azincourt]

6 minutes ago, SumGuy said:

Experience, maturity, calm, he's proven himself via life in certain and various ways, she has heard about him from her older sister and likes what she hears and sees, it turns her on.  Know it's not common but as  50+ old guy myself not uncommon, and not just about being taken care of financially.   His financially stability may be attractive, not so much about giving her money but what is says about his character.

Sure.. but that kinda makes it look like she made bad choices in the men she dated and now she's looking for a guy to clean up the mess her love life is. 27, attractive, and she doesn't have a host of young men interested in dating her? Or maybe those men aren't interested in anything more than a hook-up because they don't think she's good relationship material?

Plenty of 27-35 year old men are mature, which makes me wonder why her sister is trying to hook her up with OP. I dunno about a man's financial stability saying a lot about his character. Lots of men who are extremely rich and they ain't exactly a rose to be around.

 

Quote

A 50 year old divorced guy could make the perfect fling partner, he wouldn't rush her into marriage or a relationship and may not make it more than she wants it to be yet not treat her like just an FWB, both ends of the spectrum 30 something guys would fall in to.   She may have just met one too many marry me tomorrow or you are just the flavor of the month 20-30 something guys.

Last but not least, not all 50 year old men are out of shape and lagging in "libido," the ones in good shape and high "libido" do more than fine.  

So many legitimate reasons she may prefer him in particular, pretty sure she would not go for just any 50 year old.  The information from her sister is likely key.

I ain't seeing that.  Guy's gonna be 70 years old twenty years from now, and there are even men in their 60s who have severe health problems etc,  I ain't seeing a 37 year old woman or a 47 year old woman wanting to take care of a boyfriend/husband like the guy's her father.

Sure, but most of the men who are 50 and in shape ain't looking and feeling and physically imposing like Hugh Jackman 50 year old + Wolverine, and it's not like there aren't lots of fit 27-30 year old men to go around where OP lives, right?

Something about all of this feels off to me, but hey I ain't OP. If I was 50 years old I'd be too distracted by the thought of why would a woman this young woman  want me, to actually end up dating her.

Edited September 14, 2020 by Azincourt

[Ruby Slippers]

It's extremely unlikely this woman is trying to set up her younger sister for a fling. I'm sure she's aware she could get that herself with minimal effort. It's very likely she seems him as a good potential long-term partner for her sister. Of course his stability and resources are part of the equation. He's already proven he's capable of commitment, raising a family, etc., so seems like a "safe bet" for her sister.

But given that you didn't follow up with a second date and feel yourself pulling back, I'm guessing you're feeling the high level of risk to yourself in the situation - that being, you investing however much and then her leaving later due to the age difference. Given that you're old enough to be her father, I'd say the risk of that is quite high.

I'm pretty sure if I were a man in your situation, there's no way I'd get serious with a woman 22 years younger. By that age, most people don't want to invest in things that have a high risk of not lasting.

[SumGuy]

@Azincourt

If shes is just in it for fling, what he is like in 5 + years doesn't matter.

All I can say is such women let you know what they like about you, if you ask what they see in you.    For me they are just at too different of a life stage, rarely share common cultural references, and frankly feel like I a taking advantage of them.  My experience is limited and certainly never had a co-worker try to set me up.   I always seem to date within ± 10% of my age my whole life.

I do get money doesn't make you nice, but she has her sisters input on his character.  Basically having your financial life in order seems to be and indication you are ambitious a doer, etc.  I'm probably the last one to agree with that as a blanket statement, but it always seem to be put out there in comparison to guys who don't.

As to the OP, I'd just ask if she knows how old he is and ask what she sees in him as you are both likely at very different life stages.

[Azincourt]

At her age?

27?

She could even be 60 years old and she'd still have lots of guys lined up if they could smell casual sex up in the air. This is most likely an older sister trying to fix her younger sister's life by setting her up with a man who is far more likely to emotionally invest himself, and his money on a woman. Because, well, she's young and hot, and men fall for that ALL the time. Just look at the world leaders. Boris Johnson divorced his wife to get with a 21 year old. He's almost 60. His ex-wife is 33 years old lol. And when this current domestic partner of his turns 30+ he'll most likely get a new 19 year old.  Bill Clinton didn't cheat on his wife with a woman his own age now did he.

Quote

I'm pretty sure if I were a man in your situation, there's no way I'd get serious with a woman 22 years younger. By that age, most people don't want to invest in things that have a high risk of not lasting.

I already feel a bit ehh when I date women 5 to 10 years younger than me, because what do we have in common other than the love we feel for Linkin Park. What would I have in common with a woman, if I was 50 years old, and she was almost 30 years younger than me?

And think about her parents.

What would a father think if he saw his daughter who ain't even 30 yet bring home a man who is his own age or close to it???

 

Edited September 14, 2020 by Azincourt

[Ami1uwant]

16 hours ago, Myasylum said:

Well... I'm a dude,  not a woman.  I also have no interest in controlling anybody.  Not my thing. 

   Thanks for the input though. 

I’m a guy near your age...

 

no no problem trying it but I highly doubt this goes anywhere.

do you want to  have kids again?  Do you want yo inherit young kids if she has them?

 

if you guys have common interests and values it can work given the age differences

 

 

 

 

[Ami1uwant]

1 hour ago, Azincourt said:

Yeah... I wouldn't do that.

A woman who is in her 20s and interested in dating or marrying a man who is old enough to be her grandfather if the guy had become a dad early in life - she's usually interested in what he can do for her. Financially.  Besides that you shouldn't be calling a woman past the age of 18 ''girl,'' because that kinda demeans her, as she's an adult, but I'd really consider why you'd be interested in dating a woman who is your kids age or  close to it, other than the attractive body and face she possesses, certainly, but there's a lot more to a relationship than just wanting to have sex with a woman.

Unless you are only looking for sex, and she's only looking for a little help to pay the bills. In that case, it's fine. The economy needs stimulation anyway and college debt ain't pay itself.

Listen, I'm sure you look young for your age.

But there's being in your 30s and looking young enough for women who are 10 years younger  to actually be attracted to you because, you're well, physically attractive and you are youthful in appearance and behavior, and then there's I'm a 50 year old man interested in dating a woman who is barely out of college because.. I dunno , man. Everyone looks their age, more or less, and I don't know that many guys who are 50 and look 27. I mean, sure,  Tom Cruise and Brad Pitt can pull it off, to look like they're in their 30s.. but it's not like the average guy looks like how Brad Pitt and Tom Cruise started out, and it's not like the average guy can afford the plastic surgery Brad and Tom Can afford..Jesus Christ talk about a man's grasp exceeding his reach..

 

I have a few friends who have married women about 15 yrs younger than they are. I have known of a few other big age difference relationships.

they did have a second group of kids when there first set had finished high school.

 

im assuming you are younger and are poor st guessing aged...

 

 

[Azincourt]

10 minutes ago, Ami1uwant said:

 

I have a few friends who have married women about 15 yrs younger than they are. I have known of a few other big age difference relationships.

they did have a second group of kids when there first set had finished high school.

 

im assuming you are younger and are poor st guessing aged...

 

 

There's a bit of leeway in that example.

20 year old woman marrying a 35 year old man?

Strange to me. But doable. Miracles do happen. Although I'd feel mighty weird meeting up with a father in law who is younger than my father and only what, 10 or 15 years older than me??

But are we talking about conservative women from conservative cultures or are we talking about women from back home, Santa Monica Beach? Because I don't remember seeing a woman like that with a dude whose ride was a 1990 Fiat uno.

But a 27 year old woman with a 50 year old? We ain't talking about a 10 or 15 age difference here, the guy's literally of an age where he got to see massive world events take place, unlike 27 year old woman who has been alive for a much shorter span of time. How can they relate to each other?

Ah, so you're saying that the women you know who are young and married older men are women who married rich older men? Because the women wanted a better life for themselves and their families by trading sexual attraction and sexual desire for financial security and the house he can provide her with?

I never needed to use money to get a younger woman. I just exist. The women will either be into me or not. I don't cheat the system.  How can I win at the competition men fight amongst each other for the attention of attractive young women if I was to just pull a Boris Johnson and buy a wife?

Plus, I've never really been into the whole Saudi Arabian Prince buying a wife thing.

Edited September 14, 2020 by Azincourt