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Dating Someone 20yrs Older?

806 views 50 replies 29 participants last post by  Emerald Legend 
#1 ·
Don't know if I should do this. I really like this guy as a person and, I know this sounds weird, but I like what he says after a couple of drinks. He's also super consistent and has a pretty selfless attitude toward people.

I'm split about this. I wouldn't waste his time dating, unless I was very sure that it was a good idea. We talk to each other every day on the phone, as well as chat. Usually, they're at least 1-2 hour long conversations.

We have really in-depth conversations and also joke around really well. If he was a female, this would be the kind of friend where we'd live at each other's houses. Just based on who he is alone, we have really great fremistry.

He doesn't want to create something if it's not going to work out, but after two glasses or so of wine, he tells me all of these sweet things about myself. That's really his nature.

Twenty years is a big gap. We've talked about this before, he agrees. We went on like one date, and it got a lot of negative attention. I notice that if you date someone more than around ten years older than you, people tend to look down on that and ask you if they're your dad. There's also aging to think about. The women in my family don't hit menopause until they're in their sixties or so.

If he were younger, I'd date him. Boom, no questions asked. He's so awesome that he would still continue being my friend 110%, even without the prospect of dating. Mmm, I dunno...
 
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#3 ·
I dont get why age matter,s if the two of you are hitting it off.

The only reason I think it matters, is because it matters to you. So there for its an issue.

Just a suggestion dont look at other peoples reactions. I have dated 20+ I guess I didnt notice any sort of huge deal in reactions.

If you two have a great connection I guess I would say thats worth investigating a bit more.
 
#6 ·
Many people go through life without ever finding true love or a soulmate. So if you find one, don't assume it will happen again. I've dated girls 15-18 yrs younger, women generally age faster so when you're both older the age diff won't be noticeable. Normally, if I can get past their mom, it's smooth sailing:tongue:
 
#7 ·
I don't know where you live and what the people are like there, but personally, I don't think someone 20 years your senior is that big of a deal.

Presently, I'd really like to go on a date with someone who's nearly 3 decades older than me (would look more like 5 decades to others, due to my looking so young). If I got the chance, I know it wouldn't be a problem for me in the least bit. I wouldn't pass up such a rare connection, such as yours. And like another poster mentioned, you can't really count on that coming by again; life is short indeed.
 
#8 ·
Don't know if I should do this. I really like this guy as a person and, I know this sounds weird, but I like what he says after a couple of drinks.

.....

He doesn't want to create something if it's not going to work out, but after two glasses or so of wine, he tells me all of these sweet things about myself. That's really his nature.

...

Listen to what he DOES. Watch what he says.


Why do you like him aside from the ego strokes?


The age is a moot point.
 
#9 ·
Any two mature adults can have a healthy and happy relationship. Don't sweat what others may or may not think about you if what you have is loving and caring and makes you as a couple truly happy.

I dated an older man and the only people who judged were clueless younger men who thought they were more entitled to a younger woman.
 
#10 ·
The most significant relationship of my life was with someone +15 years older than me.

We were together for over a decade and honestly the only times it really came up was when other people expressed shock re: the age gap.

Occasionally we didn't know the same pop culture information but for the most part we did. When we didn't, we enjoyed exposing each other to new things.

In the important things like values, respect, life concepts, honest communication, sexual ideals etcetera we were completely compatible. If you are getting the impression that he values you and would treat you kindly, this is too rare of a connection to dismiss based on a superficial consideration.

Two serious aspects: Future family considerations as you mentioned. Is he "done" with having a family or not interested in having more children? You need to know how you feel about this area.

Secondly, longevity. My love died unexpectedly. But, reality is that the older partner will likely die first. That being said, I would do it all over again in a heartbeat despite the heartache. The profound love and it's memory outweighs the grief.
 
#11 ·
Who gives a fuck what others think? It doesn't concern them! I see no problem go for it :)
He might end up being a really meaningful or positive relationship; why miss your chance?
 
#12 ·
These were some really sweet messages! They've definitely given me a new perspective. Right now, my friend needs some down-time. He recently broke it off with a woman who was draining and needy, and that was a bad situation for him, because he's more of a giver. I also don't know that he wants to do a long-distance relationship. I guess you never know. I just really want him to end up with someone who will treat him well and build him up. He's a really good guy. :)
 
#13 ·
Honestly speaking, love is stupid and has no boundaries. If you find someone who loves you back just as much and treasures you, treats you the way you think you deserve to be...why let them go? Ignore remarks from those hesitant, sure they may have been hurt or won't encourage but you need to trust yourself and embark on your own journey...remember, happiness is key and having someone you enjoy.
 
#16 ·
Not to be rude, but most sixty year olds don't need a carer. Especially now days. My grandfather was young and strong at sixty, and my mother is looking like she's going to be that way too.

However, when my grandfather was in his late seventies he declined quickly, and there was an issue with his wife, who was twenty two years younger, after nearly two decades of marriage. She's kind of a bitch though, so I am not sure that's not just about her (lack of) character. My mom and uncle ended up caring for him between about 78-80, when he died.
 
#15 ·
Wow sounds like you really like each other, but I know "what people think" is harder for some people than others...it can be a struggle, there are people who even hide a partner with a significant age difference, just like an obese or same sex partner, like they are really overcome by the shame of loving someone different, like they imagine one day they'll just straighten up and meet a presentable social ideal?

There are ways to work around that, like keeping it casual for whatever length of time you need, just because you like someone doesn't mean you have to get married or have a commitment of any kind.

I think you are right to be concerned about aging, but what if by fearing that you are throwing away a great five, ten or fifteen years with him, you could just as easily not spend the rest of your life with someone your own age for other reasons.
 
#20 ·
I'm not sure how successful a long-term relationship with someone twenty years my senior would be, especially considering I'm still in my twenties, and male-female dynamics seem pretty split on the issue. It doesn't mean it couldn't work out, and how would you know if you never tried? A few people have proven others wrong.

What I'd watch out for are generational differences, position in life and the goals that come with them, financial situations.
 
#24 ·
A) You know you want to
B) You will make his old man sex fantasies with a much younger woman come to fruition
C) He will probably buy you steaks



I'm assuming OP is somewhere around 20-30 years old. Which means they'd have to be together for around 30 years before he nears death.
 
#26 ·
For me, the idea of losing or leaving someone too early or too late is too much. Fuck that. It's awful either way it is, whether you're the older or the younger, assuming you both love each other enough to last your lifetimes.
 
#28 ·
Connection is rare. I'll give it a go with someone 20 yrs older, if ever. It's a big age gap and the last thing i'd consider is what others think of it.

I've been conversing with someone 19 years older than I. We haven't met yet. I'm ok with his age but I'm not sure about his intentions. I think he just wants to make out . I'm thinking if I should consider. :/
 
#31 ·
Not to laugh at your pain, but I found it kind of funny that he "just wants to make out." I actually think this highlights a good point, though. It's not an automatic in being a younger chick. More years also means more opportunity for heartbreak, and so on. In my case, he's just not at a good point for a relationship right now, and the mortality aspect of it is a concern of his. What it boils down to is that any guy worth his salt is going to be difficult to date, one way or another.
 
#32 ·
I'm in my late 40's. Once upon a time I dated a lady 7 years my senior. Was married to her for a while.

Now I'm thinking of spending time with a lady in her early 30's. was NOT looking for someone so young. In fact, I had pretty well decided to only spend time with ladies 40 and older. I've REALLY had to examine my motives. Am I taking advantage of her? WHY do I want to spend time with her? What is the attraction?

When done, after a TON of soul searching, she is brilliant, kind, been through a fair amount in life. She is pretty happy being single, but would be interesting in spending time with the RIGHT guy. She is plenty strong enough to tell me NO if she wants. We share many of the same values, we have great conversations. she lives pretty far away.

I respect her as a person, a peer.

We shall see.
 
#33 ·
The guy I like's in his late forties. I'm late twenties. The way I see it, there's always an element of selfishness when you like someone, so it's not worth dwelling on. That's just attraction. There are a lot of different reasons for getting together with someone, not just one. I like this guy for the friendship that we have, and am attracted to his mind and rugged individualism. I liked someone six years younger than me before, because there was some kind of physical chemistry that we had, and he came from a similar background. There are a lot of things that could make a relationship work out in the long-run, and if you're going to lock-in to only one trait, like they have to be your age or it has to be love at first sight or they have to be your best friend first or whatever, you limit yourself. All of those traits exist to create options. A best friend is an option, love at first sight is an option, someone your age with your background and beliefs is an option; a random stranger is not an option.
 
#34 ·
Simply put : what does your guts tell you, Waif ? I think you should go by what is written on these glasses.

Don't overthink about all the what if, you ll never do otherwise. Fuck society's thoughts. What if this could be a truelly awesome bond that you'd never get to experience with anybody else ?

Turn off that brain. Listen to your guts. Not your heart. If they re ok with it just dont think, live.
 
#36 ·
@Waif

Nothing I said in my previous post was meant to discourage you from your own situation. If you genuinely like a much older person, please by all means go for it, but it's wrong to assume there is no difference, or that all women are ok with it. Charlie Chaplins last wife was 35 years younger and genuinely loved him.
 
#40 ·
Elderly men can be good dads. My concern would be more for the wife, or even how the wife treats him once he gets very much older.

I have similar concerns about the person I have been seeing, but in reverse. He thinks I'm hot now but what about when I'm fifty and he's not. But also what if that's ok, or even we can go both go in different directions at that time.

People need to be realistic. It actually blows my mind anyone would compare a man in his fifties to one in his twenties, thirties or even forties. Even as a child I could see the difference between my grandfather and my younger relatives. What kind of delusional moron actually thinks men don't age like women do.
 
#41 ·
This may sound cruel but you should treat any relationship as two independent whole people meeting and enjoying what they can emerge together. Everything ends even if its death that ends it. This does not mean that you become a fair weather relationship person. Love is never JUST a light thing. It always contains some heaviness. That heaviness is the part that often ensures we stick around for each other through difficult times.

That being said there are always total life inertia situations that can cause a relationship to end. The deeper you go in the cave, the longer and more carefully you have to spend coming back out. Each step in that exploration should be genuine. As long as it is genuine, you did all you could. This is the primary reason that sensing genuineness in a potential partner is an amazing skill to have. It means you can more easily make sure that they are getting JUST AS DEEP right along with you.

In the experiencing of relationships, nothing else matters quite like mutual genuine progress. Just to reiterate - NOTHING ELSE MATTERS quite like mutual genuine progress.
 
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