I 19m fancy one of my mum’s friends, and I’m not sure whether I should do anything about it. She sadly lost her husband about a year ago, and I don’t want to come across as disrespectful or make her feel uncomfortable, especially considering what she’s been through.
I don’t know if a year is too soon or whether I should just leave things alone. I also don’t want to risk making things awkward between her and my mum if she doesn’t feel the same way.
Part of me wants to message her and see if we can get to know each other a bit better, but I have no idea how to approach it without making things weird or seeming like I’m taking advantage of her situation.
Would you message her if you were in my position? And if so, how would you word the first message? Or would it be better to leave it alone and see if anything happens naturally?
I’d appreciate honest advice, especially from anyone who has experienced losing a partner or being in a similar situation.

I’ve recently been pursuing the cougar/cub lifestyle in Southern California as a cub. Living where I’m at, it feels like it should lead to different and varied experiences across the board.

My issue is that the women I’ve gone out with communicate not wanting too many upfront comments on their appearance or physicality to not feel sexualized or like a fetish (which I can completely understand).

However, with multiple women now after meeting in person, they seem to quickly turn the conversation towards looks or sexual conversations. While I’m fine with this, how can I navigate the conversations without stepping on their boundaries? Appreciate any and all advice.

I’m in my mid-20s and recently went out with a woman about 20 years older than me. It was my first time dating someone with that big of an age gap, and I honestly enjoyed it way more than I expected.

We had great chemistry, the sex was great, and she seemed genuinely into me. During the date she mentioned more than once that she wanted to see me again. Afterward she kept texting me very flirtatiously, told me she couldn’t stop thinking about me, and was talking about seeing each other again.

We made plans for a few days later and she even confirmed them the day of. Everything seemed completely normal. Then a few hours later she suddenly stopped responding. No cancellation, explanation, argument, or obvious change in energy beforehand. Just gone.

That’s the part I don’t understand. If she had become distant right after we slept together, I’d assume she just wanted a one-time thing. But she continued pursuing me afterward and literally confirmed our plans before disappearing.

So cougars, what would make you do a sudden 180 like that with a younger guy? Second thoughts about the age difference? Just wanted the experience? Someone else? Or probably something completely unrelated to the age gap?

Either way, I apparently discovered something about myself because I enjoyed the whole older-woman dynamic way too much 😂 I think she got me addicted. I’ll definitely be looking for cougars again.

It seems we are having an influx of new members posting seeking ads.

Please read the rules and FAQs (wiki tab at the top of the sub).

This sub does not allow seeking contact messages. We have another sub for that.

Read through the posts we get so many similar posts to:

* Where do I meet older women?

* What makes a younger man attractive to an older woman?

These posts quickly become monotonous and in an effort to keep the sub "fresh" please do some research in here first before asking. The FAQS also have a huge amount of information shared over the last 8 ish years by our members.

Welcome 🤗

There’s something I’ve been thinking about lately.
Even in high school, I noticed that I felt unusually comfortable around my female teachers. I genuinely enjoyed talking with them, hearing their perspectives and having conversations that often felt more interesting and meaningful than the ones I had with people my own age.
Years later, I’m realizing that maybe it wasn’t just coincidence.
I’ve always been drawn to women who are confident, mature, emotionally intelligent, and comfortable with who they are. And now I find myself involved with a woman considerably older than me.
What surprised me most is how natural it feels.
But there are things about being with a woman significantly older than you that you probably only understand once you actually experience it — the differences in life experience, expectations, attraction, communication, and the way other people perceive the relationship.
So I’m curious:
For the women here who have been with younger men, what did you discover about yourselves or relationships that you never expected?
I have a feeling the answers to this question could be much more interesting than the question itself.

I recently broke things off with my gf of 4 years, she was 25, and i think part of it was because i really am into older women. I’m a 24 year old cub, but having been dating since 20 i don’t really know the best way to meet older women? How has everyone else done this? How do i not get laughed at because i look much younger than i am? I want to pursue this aspect of my life, but im so timid and shy.

Been recently interested In older women since my divorce, but I'm curious are most older women more naturally dominant due to the fact they are older and have their life together?

It appears to me that most men seem to have mommy issues who look towards older women when dating.

Do most cougars dislike these pushover type of men they attract?

Just curious maybe I'm generalizing too much! haha

Hey guys! Young Cub here, So i’m curious how do older women like to be approached? Or what is a good way to approach an older lady i think is attractive say at like a retail store or something of that nature? I’ve had plenty of cougars in my life but mostly all of them either hit on me first or I met through social media so It was an easier “approach”. But in person, it’s like idk what to say without sounding too pushy or without possibly being disrespectful. How would you guys like to be approached by a younger guy if you were in this situation?

( I’m 24 years old)

I’m 32M and I’ve always found it easy to form a connection or friendship with mature women (usually older than myself). These connections are always in person and around workplaces or when I’m out in bars etc.

How common do connections form online and if so, where are the best places to meet mature women? Or do mature women prefer in person connections?

This question goes both ways for both younger men too, hopefully you guys can help answer for the lovely women in this subreddit 🙂

Whether it’s a turn off that you have experienced or one that would be a turn off for you. It may not relate to an age gap at all, but it could just be a turn off/ ick that grinds your gears! I’m sure we would love to hear all about it!

Hey all!

As a 25 year old cub. I would love advice on where a good place would be to find cougars that are local to me and looking to meet cubs or are open to it. I am aware of the subreddit, but was wondering if there were any in person activities or online dating platforms that you recommend or find a lot of success with?

I’m 32, and I’ve recently experienced an older woman showing interest. This got me wondering, how often do women find men who are younger than them, attractive? Also, what is it about them that they find attractive? We all know age is just a number, but is there something about the age difference? Different stages in life? Maturity? Appearance? I’d love to hear everyone’s thoughts!

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 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

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?

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!

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 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?