Older/mature men: What are your insecurities in dating?

[Miss Chrysalis]

If you're an older/mature man seeking actual connection (and not just validation from a hot 20/30 something flooding your inbox), what kinds of things do you worry about when considering a dating relationship? How does the age factor (both younger and older) impact your thoughts and insecurities or worries? 

I'm asking this from the perspective of a mature woman (but not a senior citizen) seeking to understand the thoughts and feelings of a male who is a lot older. 

[Gebidozo]

Well, as a 49 year old man dating a 31 year old woman, I’ve considered these questions a lot.

For my part, I mostly worry that I’ll be a burden to her. That if everything works well she’s going to watch me age and grow old much sooner than her. I’m also afraid of the inevitable sexual decline, which will happen to me much earlier than to her.

For a hypothetical younger partner, I’d worry a lot about lack of maturity and experience. My long-term ex was also a lot younger than me, she was indeed too young and, like all or almost all very young people, she didn’t really understand what she wanted. When she finally did, she discovered that it wasn’t me.

That’s why one of the things that makes me happy in my current relationship is that my partner is more mature and experienced than her age would normally indicate. We both have had wild pasts and we sort of arrived at the same mental destination at the same time, in spite of the age difference. We are no longer curious about mere exploration, we’re both looking for compatibility and connection and would rather be single than in a relationship where these are lacking.

Other things that would bother me in a hypothetical stereotypical younger partner are rushing into things, lovebombing, unrealistic expectations, excessive communication demands, jealousy, disrespect of my privacy, attempting to control me, pressure, emotional blackmail. My actual partner doesn’t do any of these things.

 

[Sony12]

I date older women and usually it's casual situations so neither of us have ideas of a long term relationship in mind. So not really that big of a deal. I just continue to try to stay fit so I continue to have the type of body many ladies like to have in a younger man (attractive face, trim body frame, nice stomach area.....etc.

[stillafool]

What is the age difference?

[smackie9]

Most mature/mature minded men I know prefer a mature woman for the long haul, because where they are at in life...kids grown up, looking forward to retiring with someone in the future and travel, already established financially, have more things in common.

[Interstellar]

Initially, online (and offline) it’s important to note that men will always be visual creatures. 99 percent of men prefer a woman with long, straight hair. No curly, frumpy or short to super short hair. Below the ear or up to your neck and straight is fine. You want to cast as wide of a net as possible. How she dresses, nothing revealing. A little skin is okay, just enough that you take care of your health. Bicep poses that also show your armpits are lame lol, but you sitting on a bike smiling is good, or holding a volleyball.

if you look to be younger than your age, nobody cares about the number attached to it. This is like fitness, if you look fit or toned or shredded nobody cares about how much body fat percentage you’re carrying.

Edited March 13 by Interstellar

[Foxhall]

Recently returned to the dating scene after about six years away

Mid 40s is not that old is it- but I am more conscious of being that age now- like a realisation that say under 35s are pretty much beyond me or at least difficult for me to attract.

My main insecurity now is that I feel the women Ive had previous relationships with were my best chance at love- I appear to be the opposite of a bottle of wine- Im not getting better with age,

three months ago I was thinking I have to start a clean slate find someone new- now Im thinking can I somehow rekindle things with past loves- 

will I every truly get over past regrets with relationships- that is also an insecurity preventing me from moving on.

[Miss Chrysalis]

On 3/10/2025 at 11:37 AM, stillafool said:

What is the age difference?

16 years.

[Lotsgoingon]

First of all, I would say getting into the heads of older men is NOT your problem and it's a waste of time and energy and potentially very disruptive to dating successfully. Why do you need to know what an average older guy (which is all we can say) is thinking? They all think differently. And you don't want to work to avoid triggering the insecurities of other people. That's their issue.

You cannot fix their insecurities. It's a waste of time to try to work around them. Either you like being with them or not. 

I'm older and I do a lot of activities with younger people. I don't date younger people. But I'm quite comfortable dancing with them and hanging out with them at times. I NEVER try to hide my age. For one, its pointless, foolish. I look my age and the young people I hang with look their age. I focus on the connection with the person in front of me. And part of the fun of the experience for me has to do with being older--and getting a kick of the ways of younger generations. And getting a kick out of all the experiences I've had that they haven't quite had. 

I would challenge your question in a second way as well.  I don't have insecurities about being older. Certainly fewer insecurities about my age than I did about 20 other things when I was younger. 

I assume if a relationship (from platonic to romantic) is going to work, it has to work with me being comfortable with myself and them being comfortable with themselves and we both being ok with each other. My age is part of me and their age is part of them. 

By the way, I don't have 20 or 30 somethings flooding my mailbox. Not even 40 somethings. What planet are you writing about such that these young hot women flood the inboxes of older guys?

[Lotsgoingon]

OP, a suggestion. Tell us exactly what the situation is--and your part/role in the situation. 

We specialize in dating advice here. And without particulars, people like me are going to give you dating advice.

But if you drop all the cover and tell us the details. We don't know you, you won't give names or revealing details. Tell us exactly what's going on and you'll get MUCH better answers. 

[expos4ever]

Two things concern me as a 66 year old man seeking to date women roughly my age:

1. Will they still be interested in physical intimacy? This concern includes, but is not limited to, the question of whether they really believe that a man can desire them even if they have lost the lustre of youth?

2. In the online dating context only, will women respond to a "like" (and / or a message) from a man who is not in the top 10% in terms of physical attractiveness? My anecdotal experience as a very average looking (and I do mean average - I am probably right in the middle of the pack with my best feature being slimness) is that even older women (e.g. in their 60s) still are filtering out men unless they are very good-looking. And I honestly think that inclination makes things worse for everybody (except, of course, men in the top 10%). I want to add that I think this is only a problem in the online world - in the real world, I believe women evaluate men based on many other things than physical appearance.

 

[Sony12]

Yes in the online world people often tend to be looking for a fantasy that can 'hopefully' be turned into a relationship. You find many women in their 60's on up completely ignoring men their own age because they have younger men contacting them who do a better job of scratching that itch. 

 

[expos4ever]

34 minutes ago, Sony12 said:

Yes in the online world people often tend to be looking for a fantasy that can 'hopefully' be turned into a relationship. You find many women in their 60's on up completely ignoring men their own age because they have younger men contacting them who do a better job of scratching that itch. 

 

Hi, assuming you are responding to my post, you have raised a point that I never considered - that older women (e.g., in their 60s) might be looking for younger men. But even if that's true, I very much doubt that it is in the best interests of such women to do so unless, of course, these younger men they are targeting are not in the top 10%. In that scenario, yes, I can how it would seem to make sense - because 90% of men get ignored, these ignored younger men may be willing to date an older woman because women their own age are ignoring them. 

[Sony12]

1 hour ago, expos4ever said:

Hi, assuming you are responding to my post, you have raised a point that I never considered - that older women (e.g., in their 60s) might be looking for younger men. But even if that's true, I very much doubt that it is in the best interests of such women to do so unless, of course, these younger men they are targeting are not in the top 10%. In that scenario, yes, I can how it would seem to make sense - because 90% of men get ignored, these ignored younger men may be willing to date an older woman because women their own age are ignoring them. 

They are interested in good looking younger men the same way men are interested in good looking younger women.

And many of those guys get attention from women their own age as well but choose to date older women as there is significantly less drama in that scenario. And often times there is a lot of physical chemistry. Physical Chemistry with a woman that doesn't want you to become a parent to their kids and isn't looking to you for financial stability.

No it's often not in the older woman's best interest if she is looking for a serious relationship. If she isn't though it can work quite well for them.

Edited March 31 by Sony12

[expos4ever]

39 minutes ago, Sony12 said:

They are interested in good looking younger men the same way men are interested in good looking younger women.

And many of those guys get attention from women their own age as well but choose to date older women as there is significantly less drama in that scenario. And often times there is a lot of physical chemistry. Physical Chemistry with a woman that doesn't want you to become a parent to their kids and isn't looking to you for financial stability.

No it's often not in the older woman's best interest if she is looking for a serious relationship. If she isn't though it can work quite well for them.

Thanks for your thoughts. I agree with you.

[Miss Chrysalis]

7 hours ago, expos4ever said:

Two things concern me as a 66 year old man seeking to date women roughly my age:

1. Will they still be interested in physical intimacy? This concern includes, but is not limited to, the question of whether they really believe that a man can desire them even if they have lost the lustre of youth?

2. In the online dating context only, will women respond to a "like" (and / or a message) from a man who is not in the top 10% in terms of physical attractiveness? My anecdotal experience as a very average looking (and I do mean average - I am probably right in the middle of the pack with my best feature being slimness) is that even older women (e.g. in their 60s) still are filtering out men unless they are very good-looking. And I honestly think that inclination makes things worse for everybody (except, of course, men in the top 10%). I want to add that I think this is only a problem in the online world - in the real world, I believe women evaluate men based on many other things than physical appearance.

 

Great response.  #1: I definitely do NOT believe that, sadly. #2. Do you think it's the same for men evaluating women (online vs. in the real world)? 

I've also noticed that getting to know someone in the real world, when your worlds don't necessarily coincide (you don't naturally cross paths in the course of a day) is much slower.  Probably not a bad thing since I think so many relationships that start from online dating go way too fast because there's already the assumption of wanting a relationship or an assumption of attraction from the jump.

[expos4ever]

7 minutes ago, Miss Chrysalis said:

Great response.  #1: I definitely do NOT believe that, sadly.#2. Do you think it's the same for men evaluating women (online vs. in the real world)? 

I've also noticed that getting to know someone in the real world, when your worlds don't necessarily coincide (you don't naturally cross paths in the course of a day) is much slower.  Probably not a bad thing since I think so many relationships that start from online dating go way too fast because there's already the assumption of wanting a relationship or an assumption of attraction from the jump.

Thanks for commenting. Re # 1, it's unclear to me what you are saying. Are you suggesting that older women are, or are not, interested in physical intimacy?

Re #2, In the context of online dating, I believe there may be empirical evidence to support my anecdotal experience: women are substantially more selective based on looks (that includes height) than are men. In other words, and to speak loosely, a man who is a "5" will be happy to pursue a woman who is a "5", whereas a woman who is a "5" would not pursue anything below an "8". For example, an OK Cupid survey apparently found that women find 80% of men to be "below average" in attractiveness. Which obviously cannot be right - 50% of men are, by definition, below average. Now, to be fair, this study examined "attractiveness" and not "good looks", and there might be a difference.

I fully understand that my take on this could be seen as painting women as more "shallow" than men. I want to say two things in response to this anticipated objection. First, my opinion is mostly anecdotal - based on my own experience (as someone not in the top 10% in terms of looks); that is only one data point and it is hard to be objective about yourself. Second, even if I am right, I will add that, in real life, my anecdotal experience has been that women are not more selective than men when it comes to looks - in fact, I would guess that men are more selective in this respect outside the very specific domain of online dating.

[Miss Chrysalis]

51 minutes ago, expos4ever said:

Thanks for commenting. Re # 1, it's unclear to me what you are saying. Are you suggesting that older women are, or are not, interested in physical intimacy?

Re #2, In the context of online dating, I believe there may be empirical evidence to support my anecdotal experience: women are substantially more selective based on looks (that includes height) than are men. In other words, and to speak loosely, a man who is a "5" will be happy to pursue a woman who is a "5", whereas a woman who is a "5" would not pursue anything below an "8". For example, an OK Cupid survey apparently found that women find 80% of men to be "below average" in attractiveness. Which obviously cannot be right - 50% of men are, by definition, below average. Now, to be fair, this study examined "attractiveness" and not "good looks", and there might be a difference.

I fully understand that my take on this could be seen as painting women as more "shallow" than men. I want to say two things in response to this anticipated objection. First, my opinion is mostly anecdotal - based on my own experience (as someone not in the top 10% in terms of looks); that is only one data point and it is hard to be objective about yourself. Second, even if I am right, I will add that, in real life, my anecdotal experience has been that women are not more selective than men when it comes to looks - in fact, I would guess that men are more selective in this respect outside the very specific domain of online dating.

Re #1: I meant I do not believe that a man can really desire me since I've lost the luster of youth. This probably has more to do with conditioning (and my personal experience with my ex-husband) than reality since I see plenty of women less attractive than I am being fully loved by their partners. But, it's my self-held belief I'm admitting to.

Re #2 - your thoughts are interesting since I think the same exact thing, just swap the sexes. I haven't online dated in many years, over 10 I think, but I think people tend to be less picky in person no matter the gender. Maybe not just seeing someone across the bar visually, but because they might actually talk to the person and find them attractive because of conversation. I'd pause on swiping right on a 5'6' man on an app probably, but it's not something I even notice in a person.