I genuinely would love any advice!
As a shy 20m that wants to be more brave/confident.
Whats the best piece of advice you can offer?

I’ve always had a fondness for older ladies in my life, even when i was much younger.
They are just so wonderful I feel.

I’m 32M and have recently drawn attention to older women. I think I find the attraction to be based around the maturity levels and my ability to get along with older women naturally. As I plan to connect with older women, I’d like to know when chatting, is it a label I should avoid using altogether? or is it an okay word to use in the right context?

I'm a 29M, The choice between marrying an older woman and having my own children with a younger girl is driving me crazy; My wish is to have kids, but I also love older women. What would you guys choose?

I am 32M and my work colleague is 52F. She has been pretty open with me about her dating life and I’ve often given her advice on her relationships/ flings. Although on 2 seperate occasions, she has gone to show me something on her phone and accidentally showed me naked pics of her in her gallery. She’s apologised both times stating she didn’t mean it.. is this an honest mistake or could she be interested?

Just turned 58 , been on the online apps getting a lot of mid 30’s to early 40’s interest. Decided to be open to an age gap as not really impressed with the choices in my age group. Met and have been dating a 39m for about 3mos . Likes he didn’t love bomb or come at me with all the sex talk . He’s ambitious and driven, masculine and we get along well. Where I need advice as this is new . I’m def trying to date with intent and he has expressed the same but I struggle to accept it and am questioning if I should keep investing my time. No red flags I have seen so far. I do have one family member that will react poorly that if need to deal
With if this gets serious -close sister I am just taking it day by day but worry I maybe making a mistake

I really would like to hear the answer to this I been with older woman since I was 20 I know why I love em woman my age can’t relate with me I might be young by age but I am old by life 55 year old trap in a 32 yr old body lol let’s hear it My beautiful Queens

So ive been lurking in this place for awhile now and ive had this burn question for a long time and thats how do older woman feel about trans women as a potential partner im 23 from maine usa ive always found older woman to be very attractive but ive also felt like they most likely wouldn't want to date a trans woman especially a no passing trans woman im not the greatest at wording my thought adhd kicks my ass

I’m 42F and relatively new to the older-woman/younger-man dynamic, and something has genuinely surprised me: just how many younger men seem specifically interested in women my age.

Obviously I understand the physical/sexual attraction part but What I’m much more curious about is everything beyond that.

For the younger men here who genuinely prefer older women, what is the appeal?

Is it confidence? Experience? Independence? Conversation? Less insecurity? Knowing what we want? Is there sometimes a nurturing element involved?

And I have to ask: is the whole “mommy issues” thing mostly an internet joke, or do some of you recognize that there actually is something psychological about being attracted to an older woman?

From my side, I really enjoy younger men’s energy and enthusiasm. I spent almost 20 years with a man who was older than me, and toward the end of the relationship our energy levels, sex life and lifestyles had become very different.

Experiencing younger men now has been a complete contrast. There’s an energy and excitement that I find incredibly attractive.

But I’m also realistic about age gaps. A 15–20 year difference isn’t just cosmetic. Eventually you’re reaching different stages of life, aging at different times, dealing with health, retirement, etc. So I wonder how younger men think about that too.

When you’re attracted to a woman significantly older than you, are you usually thinking “this is hot and fun while it lasts”, or could you genuinely see yourself falling for her?

Basically, I’m fascinated by the psychology

This older woman (late 30s-40s) at work showed interest in me ( mid 20s ) and wanted to go on a date. We shortly discussed about it the other day but I kind of got stuck on where so I’ll get back to her tomorrow and wanted to tell her the movies but I want to know from an older woman’s perspective is it cheesy? Bad idea ? Good idea ? I was thinking we can start with that and go from there but I’m open to suggestions.

I’m a 24 Male. I just wanted to know, in our current society do older women tend/prefer to meet on a dating app or in a social setting?
I know it depends for every female but my question is where should I consider looking ? (Even here counts lol)

Before I share my whole story about this woman and genuinely ask for advice, is anyone in the military or a veteran? I've served in the Navy since joining at 17 almost 2 years ago and it's a really big factor in my case. I do genuinely love this woman and she happens to also be a genuinely very attractive woman. But we don't speak the same language and she had 2 kids that are 10m and 9f. It's a really long story that I'm working on in my Google docs before I share, just want to make sure if anyone is interested in my story or thinks they can genuinely advise me.

Hey all!

Question here from a 27 M here. One thing or barrier i have come across when talking to older women or going past friendship has always been the family/friends comment. A fear of how introducing a young man to their personal circle which has led to many barriers. While I present as much older, my age does not change as many state they dont know my age untill I tell them. Love to know how others handle this! I know some couples do great and some do not!

I’m currently navigating a situation where a man who is over 20 years my junior (49M/71F) is interested in dating me. Initially, I was hesitant and refused to meet him, but after two months of persistence on his part, I finally agreed to meet for a drink which led to dinner and
a enjoyable golf date followed by dinner the following day. We’re planning to see each other again in a few weeks. However, I’m feeling hesitant about continuing this relationship due to the significant age gap.
Am I being too rigid, or am I reasonably protecting myself from potentially being a placeholder until he finds someone closer to his age? He has expressed that he finds me attractive and has been very complimentary. We’ve maintained daily communication since our date, which is important to me in any relationship.
While we have different lifestyles, we are exploring shared interests, such as golf and food. Still, the age gap is continuously on my mind and causing me to hesitate. What do you think?

I (19M) dated a 28-year-old woman for about a year. I know the age gap sounds crazy, and trust me, I’ve heard every opinion on it since.

At the time, though, I felt like the luckiest guy in the world. She was older, confident, had her life together, and constantly told me I was “mature for my age.” That made me feel like I was different from other guys my age, and I completely bought into it.

As time went on, things started changing. Every disagreement somehow became my fault because I was “too young to understand.” If I questioned something, she’d remind me she had more life experience. I slowly stopped speaking up because it was easier than arguing.

I also started noticing that I was always the one making sacrifices. I’d rearrange my plans for her, drive to see her whenever she wanted, and generally fit my life around hers. I earn good money for someone my age, and although I never minded being generous, I can’t help wondering if that became part of why she wanted me around.
The relationship eventually ended after I found out she’d been seeing someone else behind my back. Somehow, she still managed to convince me I was the problem because I “wasn’t mature enough.”

Now that I’ve had time to think, I don’t believe the issue was the age gap by itself. It was the imbalance. I spent so long trying to prove I was mature enough that I ignored the fact I wasn’t being treated with the same respect I was giving.
Has anyone else come out of a relationship and realised afterwards that you were overlooking obvious red flags because you were so invested in making it work?

I'm new to this sub! Wasn't sure where to ask this advice and thought this may be a good place to start.

I've very recently developed feelings for a guy I've been working with on a local committee. We've known each other for years, but recently started working closely together earlier this year when I became Chair and he became Vice Chair.

He's 33M. I'm 48F. He is mature for his age and I give off much younger vibes.

He consistently downplays our age difference whenever I bring it up. Before his birthday, I said something about forgetting how old he was turning but it was a lot younger than me. He said probably not that much. (He knows how old I actually am; we've had that conversation many times.)

Then he mentioned something about a young professionals event and I joked that I didn't get an invite bc I'm too old and he said he even feels old there bc it's all Gen Z kids and they say weird things lol and he says he feels like he relates more to my age.

Recently we were at another event. I was hugging everyone when they were leaving and went to hug him. He looked terrified! It was a very quick, awkward hug.

But he texts or calls (yes, calls!) me often, generally a couple times a week, mostly to talk about committee stuff. But we often talk about personal stuff as well like weekend plans, our day jobs, or hobbies. One night back in March (when we first took our leadership roles) we talked for an hour and a half. That night we talked about all kinds of stuff like where we grew up in town and all sorts of things.

One night recently after a meeting, we stood in the parking lot talking for like 20 minutes. He was in no rush to leave even though he had to get up early the next day.

It seems like even more lately he's been finding reasons to call or text. Like vaguely committee-related, but absolutely nothing urgent.

Would it be safe to say he's interested in me romantically? Or is he just being friendly?

He's been nothing but respectful, professional, and helpful. I suspect he's holding back to not cross a line because of our leadership roles and age difference. I think he's looking for a subtle green light from me to proceed. But I've been very wrong about male behavior in the past, sooo help lol.

Google Gemini says he's interested lol. What do you think?

First time posting here. I’m 55, 5 years out of divorce and not looking for marriage/relationship escalator.

I’ve always dated younger but in the past it was only small gaps. I’m not keen on being labelled a cougar as it feels so predatory.

Since divorce I did have a lot of interest from significantly younger guys and it was fun to explore before I was ready for anything more serious. Then I did get into a committed relationship for 18 months and now ready again to dip my toes back.

I thought I was happy with solo poly but starting to realise I think that is mostly protecting myself from caring too deeply about one special person and maybe it’s time for me to get past that.

Anyway I’ve recently started a lovely new connection with a lovely 34m. When we started chatting I wasn’t expecting it to go anywhere but it’s been a couple of weeks of consistent and engaging messaging as well as one very lovely date and talking about arranging the next. He seems like a real old school gentleman and says he tends to date older (though also not quite as big a gap as this).

But I’m getting in my head a lot about can he really take me seriously and is that going to get in the way of this moving forward if it isn’t just for casual fun.

I’d love to hear from the cubs what it’s like for you with such a big gap (55f and 34m) and if you’re thinking more in terms of a fun short term experience vs actually genuinely interested in something more real and sustainable? At the moment we feel like a good match but I worry about what happens in 10+ years as I move into genuinely older age? Obviously a huge projection given we’ve only met once, but I’d like to hear the reality.

Always loved the song Qui and never imagined I might be considering myself in the much older lover role

Thanks!

A bit like Jude Law and Susan Sarandon in Alfie.

Against all odds, you meet a woman online or in the wild, it seems unreal. You have an unusual attraction and somehow you have found your way to each other. She ticks all the boxes. You start getting to know each other and you have visions of a relationship. She tells you of her divorce and you respond by balancing being sympathetic to her pain while showing that, in all the important ways, you are nothing like her ex. She mentions that she has been in a few relationships since her breakup. One was with a guy younger than you and it only ended because the guy could not stand up to his mother. And your response is what...

Hey all,

genuine question here! I am in my mid to late 20s. I always have enjoyed and admired older women. I dont like using the term cougar and cub. My question here for you, what are some preferences you all look for when admiring younger men? I know everyone has types but I mean like rules but also what sort of things tell you "yea I like this guy"

I am a handsome fit muscular guy and I frequently go to the gym in the mornings, older women also happen to be in abundance and there are some very attractive older women who have glanced at me and definitely eyed me. I’m stuck in this endless loop of constantly making eye contact back and forth. My question now is how do you approach an older woman at the gym? In my mind I thought that properly introducing myself and also congratulating her on her fitness would be a good opener. I’m curious what are your takes on this older women of Reddit, have you ever been hit on by a younger guy at the gym? If so how did that go?

I 30M never dated someone older than and im quite open to anyone 40-50 range but Im not sure how to approach them or where? I dont wanna get tangled with someone who might be married or wanna have an affair either, any tips?

A young man says he doesn't want to date women his age and wants to date older women for their maturity/wisdom and etc. does that make you cringe or give you the ick?

I'm just personally skeptical that any reasonably minded, and attractive woman would bother with some under experienced guy. Am I wrong? Is it just a fetish invented by adult movie industry

As a soon to be 25 year old man, who's had his fair share of dating beautiful women from different walks of life, and also as someone who recently broke off with their long term partner, who was around my age, I can say for certain, there are specifc qualities in older women that I really do admire and makes me wanna be with them more than girls my age. Of course I can't put every woman in the same basket, and whatever I'm saying is completely anecdotal. I'm a man that values honesty, communication and most importantly intimacy, without playing games. I'm busy and ambitious, the last thing I want is an immature woman who plays hard to get, or have a fantasy like way of looking at dating. The beautiful women I've dated who were older than me, had those qualities- communication, honesty, care and more important the energy to be intimate. I do have a high sex drive, but I also love forming a bond before getting intimate. This post might be taken the wrong way and come across as me trying to position myself as a messiah lol. But I'd love to hear yall experiences, being with the opposite gender, in this dynamic. Women and men alike.

just wanting to know how to approach this :)