Should I lean into dating older women? (25M currently dating 41F)

[ToastersGonnaToast]

I'm a 25-year-old guy dealing with some pretty messy relationship stuff right now. A couple years ago, a bad breakup nearly wiped me out financially, and it took me a while to feel ready to start dating again. When I finally did, I ditched all the dating apps and most of my social media - kept Instagram but that's it - and decided I'd rather meet people face to face instead. For context I met my ex who cheated on me with an ex business partner and left with 30,000 dollars they took from the business account.

Since making that change, I've gotten involved in some new groups of people, surfing, painting, cooking class and I keep hitting it off with women who are older than me. A bunch of them have actually asked me out, which is how I ended up with Emily, who's 41. We met when I was just chatting with her at a farmers market while hanging out with some friends and trying some food. 

Things have been going really well between us - we go on regular dates, we're intimate both physically and emotionally, and we talk on the phone pretty much every night until one of us falls asleep. But my mom and my two older sisters won't stop giving me grief about it, especially my mom who's dying for grandkids. Little does she know I'm planning to get a vasectomy pretty soon, plus my sisters are old enough to meet someone and have kids in the future. They're just not into the idea of a serious relationship right now.

My female friends (god bless them) tried hooking me up with people they knew closer to my age - friends, cousins, - but those dates never went anywhere. I'd always end up hearing stuff like "You seem awesome but I really wish you were taller", or my personal favorite "I believe someone like you is meant for me later in life", which left a sour taste in my mouth. They even tried helping me tune my Bumble profile before I deleted it, to no avail.

Enter going out with older women. The tone completely changed to "you're so cute and interesting" and "I feel like I've known you my whole life" and sometimes flat out kissing me on the spot in front of people. Now that I'm going out with Emily, some of my friends make these comments about how she wouldn't really blend in with our crowd if they ever met her. And also sometimes saying I should return to dating apps, which vehemently refuse to do.

But here's the thing - every time I meet someone in person, it always ends up being an older woman, with younger women almost never being interested in me. At this point, I'm thinking maybe I should just roll with it. On top of all that, Emily's been talking about how she could see us getting serious, and I'm definitely not opposed to the idea.

So I guess what I'm wondering is - should I just embrace this whole dating older women thing since that's where I get the most success now? And how do I deal with everyone else's opinions? Do I just ignore it all, or should I continue to lean into this?

[smackie9]

Not everyone fits the cookie cutter life of meeting your high school sweetheart, get married, have kids, white picket fence, etc.  You follow your heart.You understand what's ahead of you if you choose this route. Obviously not many would agree with it but this isn't about them and their happiness...it's about yours. You live your life the way you feel will make you the happiest. If things don't work out, so what, tomorrow is another day. 

[Sanch62]

If you're old enough to date, you're old enough to nix the noise of others about it. Nobody else is living our love lives for us, so nobody else gets a vote.

[Sony12]

If you are looking for an actual serious relationship you probably shouldn't embrace it. Most women who date younger men aren't looking for anything long-term that could turn serious from them. Usually they just want a good looking younger guy to spend time with.

It's up to you to decide but you shouldn't do it just because you are having more luck with them. You should do it if what they offer aligns with what you are looking for from a relationship.

Edited November 2 by Sony12

[ExpatInItaly]

Date whomever you want. 

I will caution you against assuming "older women" are some broad category, though. I am 44 and there are just as many women my age who aren't into younger guys or wouldn't behave this way either: 

On 10/28/2025 at 1:04 AM, ToastersGonnaToast said:

The tone completely changed to "you're so cute and interesting" and "I feel like I've known you my whole life" and sometimes flat out kissing me on the spot in front of people.

People are invividuals. Some people are like this and some aren't  Age doesn't have a lot to do with what you're describing above here,  so roll with what the individual is showing you. If you like her and she likes you, nobody else gets a vote. 

[Sony12]

Again it all depends on how compatible it is with what you are looking for from dating. The OP doesn't really mention in his post what he is looking for (and who knows if he is even going to come back and follow up on his message because his message was made about a week ago). If you are someone who is looking for an actual meaningful relationship and don't want to merely be an older woman's casual boy toy I would be leary of women who are asking for or giving their information out to younger men they meet at farmer markets. 

Nothing at all wrong with age gap partners getting together (heck I have done it most of my adult life) but it's important for younger men who do get involved with older women to not take things too seriously (and if he is posting about it here I have a feeling he might be taking it seriously). Most women who date younger men are dating them for many of the same reasons men date younger women and will objectify them just as much as men will objectify younger women. 

It's important for the guy to not get upset because the older woman has given him head a couple times already and the thrill has started to wear off for her and so she proceeds to call it off.

When you date older women you have to take it for what it is. 

[Els]

How do YOU feel about this woman? Do you want a relationship with her, or are you just "not opposed"?

Ignore the whole grandkids thing, especially when you yourself don't want kids and are planning to get a vasectomy (good on you by the way - don't have kids just to make your mom happy, that's a terrible idea). 

But also this has to be something you're genuinely comfortable with. 25 and 41 isn't a huge age difference IMO, I'd be more concerned if you were 18. 25 year olds are mostly adults by that stage, and 41 isn't so old that you'd be doomed to become a caretaker within the next decade. But there's this weird feeling of defeatedness in your post, and you seem oddly lukewarm about the woman you're dating. Like, if young women all of a sudden started expressing interest in you, would you still want a relationship with Emily?

If you wouldn't, then don't proceed. It's unfair to her and to yourself. But if you would still want it, then go for it, and tell everyone else to shove off. 

 

[Sony12]

It would also be interesting for the OP to come back and mention how long the two of them have been getting together. Have they been dating and communicating by this point for months. Or did he make this thread after they had only talked for a short while and met up a couple times? He doesn't really specify in the lone post he made.

I know I have always been one to not tell my family about the majority of the older women I meet up with because I know they would say the same thing the OP's family has said about it.

[FredEire]

Well firstly, to hell with other people's opinions.

These days older women love younger men and aren't as in to guys their own age. When I was your age I dated a few girls in their early-mid 30s.

Just decide early what it is that you want. Most women are probably going to want a toyboy and aren't expecting you to stick around. Always be honest and clear about your boundaries/what you are looking for.

If you want to start a family, I would say dating women in their 30s and 40s with a view to settling down is not the wisest choice. If you don't then have at it. Someone who is older has been through it all and is more likely to be grounded in themselves, it's rare to meet someone in their mid 20s who isn't all over the place. So tl;dr since you said are planning to have a vasectomy I say go for it and don't give a f about anyone elses judgement if you meet someone who makes you happy.

Edited November 2 by FredEire

[Sony12]

54 minutes ago, FredEire said:

Well firstly, to hell with other people's opinions.

These days older women love younger men and aren't as in to guys their own age. When I was your age I dated a few girls in their early-mid 30s.

Just decide early what it is that you want. Most women are probably going to want a toyboy and aren't expecting you to stick around. Always be honest and clear about your boundaries/what you are looking for.

If you want to start a family, I would say dating women in their 30s and 40s with a view to settling down is not the wisest choice. If you don't then have at it. Someone who is older has been through it all and is more likely to be grounded in themselves, it's rare to meet someone in their mid 20s who isn't all over the place. So tl;dr since you said are planning to have a vasectomy I say go for it and don't give a f about anyone elses judgement if you meet someone who makes you happy.

I couldn't tell you how many times these older women would tell me they wanted to rape or molest me. Have even been told she was going to kidnap me. The age gap is a 'thrill' just like a highschool guy dating a 'cheerleader' just because she's a cheerleader. Or a highschool girl dating a guy from the football team just because he's on the football team.

Edited November 2 by Sony12

[Sanch62]

1 hour ago, Els said:

Ignore the whole grandkids thing, especially when you yourself don't want kids and are planning to get a vasectomy (good on you by the way - don't have kids just to make your mom happy, that's a terrible idea). 

While I agree with the spirit of this, I'd temper it with some caution and patience. If you're dating older women who don't want children anyway, then chances are they've either had some kind of surgery or that's on their own agenda.

I say this because I've known MANY singles and couples in their late 20's through 30's who never wanted children, weren't even interested in discussing the possibility, yet at some point later, they not only wanted them, they worked hard to make that happen.

You never know what the 'future you' will want, no matter how certain you are today. Reversing a vasectomy never carries a guarantee of success.

I've never wanted children, and I'm your grandma's age. So I know what being 'sure' is. Yet I did wait until my late 30's for a surgery I needed anyway, and chances are, many of the older women who interest you may have already done this as well.

Edited November 2 by Sanch62

[FredEire]

16 minutes ago, Sony12 said:

I couldn't tell you how many times these older women would tell me they wanted to rape or molest me. Have even been told she was going to kidnap me. The age gap is a 'thrill' just like a highschool guy dating a 'cheerleader' just because she's a cheerleader. Or a highschool girl dating a guy from the football team just because he's on the football team.

A lot of the time, yes.

If an older woman is looking to settle down, a guy in his mid 20s is generally not a good pick. Hence OP most women you meet won't be looking for this.

However there are always exceptions to the rule, I have a friend who is almost 40 and in a serious relationship with a 29 year old. So you have to filter for what you want, a relationship is possible but its going to be rare.

[Els]

On 11/3/2025 at 3:49 AM, Sanch62 said:

While I agree with the spirit of this, I'd temper it with some caution and patience. If you're dating older women who don't want children anyway, then chances are they've either had some kind of surgery or that's on their own agenda.

I say this because I've known MANY singles and couples in their late 20's through 30's who never wanted children, weren't even interested in discussing the possibility, yet at some point later, they not only wanted them, they worked hard to make that happen.

You never know what the 'future you' will want, no matter how certain you are today. Reversing a vasectomy never carries a guarantee of success.

I've never wanted children, and I'm your grandma's age. So I know what being 'sure' is. Yet I did wait until my late 30's for a surgery I needed anyway, and chances are, many of the older women who interest you may have already done this as well.

It's true that you never know what will change in the future, but having kids is an equally irreversible choice, yet most of us wouldn't advise a person who is sure that they want kids to wait until their late 30s to make that decision just because "they might change their mind". Generally speaking, when it comes to making life decisions, I think at some point you just have to go for what you want, even though of course there's a risk to every decision that you make.

In the OP's case, a 41yo can still get pregnant. He could still end up dating another woman who's younger. He could (and should) wear condoms, but they aren't failsafe. IMO if he's sure he doesn't want kids, a vasectomy is not a bad decision at all.

Also, I'm sure it varies by jurisdiction, but where I live a vasectomy is not an instant decision (or at least it's much less of an instant decision than having sex with someone!). There are several consultations prior to the procedure, and generally the process takes at least a few months. They will advise him that it's not necessarily reversible, and also work through the potential future scenarios with him.

Edited Tuesday at 03:28 PM by Els

[Gaeta]

On 11/2/2025 at 12:35 PM, Sony12 said:

I couldn't tell you how many times these older women would tell me they wanted to rape or molest me. Have even been told she was going to kidnap me. The age gap is a 'thrill' just like a highschool guy dating a 'cheerleader' just because she's a cheerleader. Or a highschool girl dating a guy from the football team just because he's on the football team.

Do not put all older women in the same basket. You met older women for sex, these women were driven by sexual fantasies. Not ALL older women dating younger men want a toy boy. 

OP: I know many couples with the lady being older, my relationship included. People and family talk at first and then they get to know the person they shut up about it. At the end of the day you don't lay down in bed with your friends or your mother and sisters. YOU get to chose who you will love. You cannot date an older women if you don't have the guts de defend her and your relationship. 

[Gaeta]

On 10/27/2025 at 8:04 PM, ToastersGonnaToast said:

Little does she know I'm planning to get a vasectomy pretty soon,

I don't know where you live but this might be impossible at your age. The medical field knows that what we want at 25 is not what we might want at 35. Many doctors will refuse to perform a vasectomy under 30.

[swenann991]

OP, Enjoy with Emily, life is to short.

[Sony12]

I do at times wonder why people bother to post topics here when they don't even bother to read the replies. The OP registered on 10/27 and it says the last time he logged in was 10/28. So unless he signed out he hasn't even read any of the replies within the thread he started (since the first reply wasn't made until 11/01).