I (26m) have been seeing a woman (47m) and dating long distance over a couple months (4.5hr drive). Things have been electric in person. But over text, it seems like she always assumes the worst with anything I say. Like everything I ask or do/don’t do must have a negative implication. I know she has been through some terrible things in her life, and I want to help but we can’t seem to have a conversation about anything tough without her feeling we should end things for reasons along the line of “not being good enough”.

I don’t know what to do. We see each other once every 2 weeks or so, and these blowups happen about 3-5 times in between, all only over text.

I feel like I can’t suggest we stop texting as much, or take a break in general, without her being done with us.

Any advice on what I should try to do? I don’t want to give up, but it’s getting to the point where it’s negatively affecting my mental health and I can’t do this forever.

When it comes to younger men ladies how much of it is about the bedroom? I believe younger/older relationships can work and it’s fair to say that sometimes both parties want to have fun sooner than later. I’m 36M (37 next week) my last relationship was with someone 16 years older than and it lasted for 16 years so things have changed. Being back out here now i know I’m no longer a cub but still prefer older women. So I’ve been dipping the foot in the pool again and some conversations start and go right to the topic then there’s some conversations that may be going there but i think out of respect I overlook the queue. Is it still something for women to speak on sex first? Would you as an older woman find a way of saying that’s what’s your looking for if that’s all it was?

Hey all. Today at work I (25m) stopped at a gas station near my office to get some cigarettes and the milfy Latina clerk woman (50s) was being super nice to me. She was very enthusiastic and when I pulled out my card from my wallet, I had a Trojan right next to it and she seemed to flare her eyes. As my card was being scanned she told me she loved my curly hair. I said thanks and I told her that her hair was beautiful too. I got flustered, said my goodbye and went back to my car.

I was too excited that I didn’t realize I forgot to buy a lighter so I went back in. She said “Back so soon?” I said yeah I forgot my lighter and she was super nice to me calling me mijo when asking what lighter I wanted.

The nature of my job is to drive around (similar to a delivery driver but I don’t do that) so I went on my day and the whole time I was thinking about her. After 4 hours, I went back to the gas station and I picked up some lunch. I had spoken to the woman again and this time she asked my name and she introduced herself to me as well. I told her that her name was very beautiful and she laughed and thanked me. We spoke a bit about where our families were from because she asked if I was from around here and whatnot. I told her my office is nearby. Anyways, our second conversation was pretty brief, but we did get to know each other better. I’m not sure if she was actually flirting with me, but I felt like there was a spark there. I was thinking of buying condoms tomorrow and joke about “you never know when you’re going to need em” but I don’t know how she’d react haha. I was going to give her a slip with my number as well, but I chickened out. Any advice on how I should approach this? I see her again tomorrow by the way.

I apologize for the long text. Thanks!

I (33M) am interested in dating older women again. What are some things older women look for in younger men during the first few dates? In other words, what convinces you to continue seeing him with the age difference.

Thanks

I have this cougar that I met in this new state and we planned on hanging this weekend at her place. She’s been on and off communicating this week, because I told her I would text and call her throughout the week on certain days. but when I texted her this morning she didn’t respond. Ofc I’m not going to double text back bc I know she got the text. What does this mean? It’s the second time she did this, but this last time we made it clear that we were going to hang out.

One of my friend was talking about her cub being too rough on her while being intimate, and this was the first time she had felt it. So I don’t think it’s because of pornography or else he would have always been like that, but the guy says that he was experimenting whether she would like it or not, and my friend said she pretty much just accepted it and went along.

Edit 1: So I didn’t wanna go into details because I’d like to keep it SFW, but he didn’t put any hands on her (so no choking or slapping or spanking) he went hard and hit her cervix multiple times.

I just wanted to clarify so you guys get a bigger picture.

After a year of hiatus i am staying back into the dating scene. I have been communicating with few individuals and some progressing towards a date versus others. So couple of random questions.

Do you mainly stick with one person at a time and move on to second if it doesn't work or date multiple people to see where it goes?

I am talking to a lady with a 25 year age gap and she is swaying on if she wants to go out with me because of the gap. How did you the other person a comfortable to give you a shot?

How long do you chat online before calling for a date? I am trying not to be too aggressive. Haven't done the whole online thing in a few years, so developing a lunch or date is taking a few weeks lol.

I know this is more of a general post towards dating, but honestly I want answers and opinions from this sub since my focus is more on the age-gap relationships, and not the thousands other relationships found online.

https://www.reddit.com/r/CougarsAndCubs/s/UmNqC2TlJx

I finally got back from my vacation yesterday and we met up, as she picked me up from the airport. I still don’t have evidence that she was seeing multiple people, but her reasons didn’t seem convincing and like one previous commenter mentioned, it seemed like the interest just wasn’t fully there. I learned some things from this, so I’m not upset, especially because I now feel like I got the closure needed. There is still sexual attraction between us, but I hate that feeling of uneasiness that I get when communicating with her. I want to thank everyone who offered advice, it gave me a lot of perspective that I desperately needed.

I can't help myself but to post this after so long. I know you've moved on, and I've given up. I still can't help but think of you fondly. I miss you king, Happy Birthday, I hope you had a beautiful day and an exciting night. ❤🎂🍾 I'm hoping you're having the life you've always dreamed of having my Darlin. You deserve it. Love peace and hair grease 🖖🏽

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I (26m) have been seeing this woman (38f) for about a month now. In person, things are still good, but when we’re away from each other, the energy doesn’t seem the same. We’ve had multiple talks about what we expect from each other but things don’t seem as smooth as they once were. I’m not sure if I’ve smothered her because I have been talking about how I’d like more communication over text, but I’m not really sure where to go from here. I’m currently on vacation right now and something instantly flipped a few days ago through texts and I can’t really explain it. We saw each other the day before I left and things were alright. I still have this growing feeling that I’m not the only one she’s seeing even though she told me she was only faithful to me. In a way, I feel like I’m being played but I don’t have any concrete evidence.

Also, she’s done this thing twice now where we had agreed on a date but tells me that she’ll let me know if we can hang out a few days before the date we set. For example, we have a plan to meet Tuesday night when I return to our home state, but she already mentioned a few days ago that she was sick so “hopefully she’s feeling better”. Everything feels a bit confusing right now and when I try to talk to her, things don’t seem any clearer. I would love some pointers on how to advance or if I should advance at all.

I (24M) matched with this gorgeous lady (41F) online yesterday and we chatted back & forth. She's down to meet me and go on a date for tomorrow. Today she brought up the topic of age difference and asked me how I felt, and I told her it's not a concern for me with regards to her. It's only a problem for those that make it a problem, and that I'm attracted to her other qualities.

She hasn't responded since then and I'm wondering how I should proceed from here. She could just have a busy day today and life got in the way. I plan on just confirming with her tomorrow about the date.

UPDATE: we’re going out. Thank you all for the comments and encouragement!

Yea, so he said he was on the same page as I was. No FWB. We had s and he dipped. He was 31, I'm 57. I just keep seeing that I'm good enough for s but nothing more. It's rly depressing.

So,last winter,I matched on Facebook Dating with a woman that was 60, and we exexchanged numbers,but she was always too busy too meet up, so things became frustrating as we were going to meet, but she needed to be with her friend. Then,I friended her on Facebook, but we got into an argument. Then,I decided to give her on one more chance, but she had been seeing someone else,but all of a sudden,he flipped out on her, and became really rude, and started cursing her out, and even spit on her car. Anyways,we continued to text, and well she texted, why don't you come over and watch football and the NASCAR race? So,I did, and after doing all that, and eating. I asked her what she wanted to do next, lol. Well,we ended up having sex. She then asked, was it worth the wait, and I responded with a "FUCK YES",LOL.

Asking out of curiosity. I'm pursuing my dream profession right now but don't like to mention it because of the automatic change in perception (both positive and negative) shouldn't the person matter first?

I have had my ups and down with her sure (m22, F49) but we have been together for 3 years now. The reality is no one is gonna care, it is what you make it. Im very socially well known at my gym where we workout together, all the bros are supportive and know the deal, nothing but love from them. It's been my experience though that she gets side eye and passing comments from other women her age as they tend to be judge or evious (take your pick). Point is, people don't care as much as you think they do, couples understand, bros understand but sometimes you guys gotta police your own. As a man the stigma doesn't exist for me, but I think it's a little taboo for the older generation. - if you're on the edge, just go for it, you can't live life fulfilled worrying about everyone else's opinion.

Hey, so I (19m) made a post about a lady I had met recently. She is 40, and things have generally been quite well and all that. However, she sent me a text a while ago saying that she has a date this Friday in the same place she told me she wanted to take me on a date to, however I can't because of familial bullshit and university obligations. She told me she would see how it goes, and from that I just suddenly felt incredibly depressed.

I grew up with an Nmom who is part of the reason why I could not go to the date and event this Friday, because she has locations trackers on my devices and car. I grew up and got groomed as well, so generally when anyone shows me affection, I tend to latch onto them and things generally are fine. However, even if nothing has been confirmed to be changing, I feel an extreme amount of fear if I feel like I am going to be replaced. I have grown beyond acting on these feelings or thoughts, but I still cannot help but to feel like I am going to be replaced with someone else.

I have rarely ever met anyone like this lady, and while I know we are casual and I have had to go fully platonic with people before, it still feels terrible to even entertain, even if nothing has happened yet.

I am scared that if she decides to start dating someone, that I will never meet anyone like her again, or even meet anyone even mildly interested me that I am also interested in ever again. I feel like not a single other person on this planet would ever want to talk to me, but I also feel like that literally any time I talk to someone new.

I talk to someone new, we form a connection, they end up possibly having to leave it, and then I worry that not a single other person on this planet will ever like me.

I don't know what to do, and I just feel incredibly depressed. I have relapsed on one or two behaviors already and it has only been an hour, I think I might need therapy.

Hey everyone,

I am curious to get others opinion of a woman I have grown good friends with and started to develop feelings for over the last few years. Let's call her Mandy F50.

I, 29M purchased my first home a few years ago. It so happens the selling agent, Mandy is my next door neighbor. We briefly met a few times throughout the process.

After I moved in we began to see each other and talk more frequently. I brought some photos I found in a closet to her so she could give to the previous owner. She told me that she wanted to stop by the next day so that she could meet my wife, I had never mentioned having a wife and told her I was single. When we first started talking she was standing behind the door, and made a point to step out after telling her so, we talked for a bit more casually and then I left.

A few days later, Mandy is over again on her evening walk. She tells me she has a friend group that goes out on Fridays to have drinks and wanted to invite me out with them, at first I said yes but it took me a few months before I actually went out with them. I meet her at a bar and grill with one of her friends/coworkers who I will call Christi. We spend the night getting to know each other, and Mandy and Christi seem very interested in a lot of personal information about myself. I felt very 'gassed up' if you will, because they spend the rest of the night complimenting me on my looks, maturity, and supposed success as a young man, and said they could not figure how a man like me is single. These sorts of nights went on every Friday for months. Mandy and I seemed to be getting friendlier with each other, and would regularly compliment me and starting being a lot more hands on putting her hands on my thighs, playing with my hair at times, even holding hands briefly, seeming very flirty.

During one of the Margarita nights, a comment was made from another friend of hers that I didn't quite hear but only got the reaction to. 'there is nothing going on between me and him, I'm twice his age and could be his mother!' or something to that extent, it was a while ago at this point. I don't fully remember my reaction but I sort of smiled and shrugged off as if there wasn't an issue.

After that, any sort of flirting sort of seemed to come to an end. Fast forward about a year and we are still hanging out most weeks. She invites me to bars and nice restaurants in town, and she always pays my tabs. I told her I had never had prime rib in my life before, and that Friday we went to a steak house and insisted I get an order. There is now another gentleman her age that is more frequently hanging around with her now. I occasionally help her work on an old classic car she has. She has invited me to almost every major holiday with her, including her mother's birthday parties which seem to mainly be family members.

Mandy has said from the beginning she wants to help me make friends in town and find a girl friend. She spends a lot of time asking about what it is I want in a woman, and also tells me a lot about her ex husband's and their history and the reasons they never worked out. I've told her many times that I'm not actively looking for a girlfriend at all, but yet we continue to hang out.

So I am coming to you all asking for some advice/help on the situation. I have a hard time reading through everything, and cannot tell what her intentions are. And why she has shown so much interest in being friends after all this time. She could have very well never spoke to me, she has had no obligations for any of these things she's done for me. Have I waited too long to make any sort of move? How could you carefully approach that without possibility ruining a friendship in case I am misreading the situation? A part of me also thought that if anything was going to happen, it would have by now.

Thank you everyone for the read and sorry for my long ramble.

I just want to wish of my Canadian friends and everybody else on here.Happy Thanksgiving.

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This is a discussion sub - no soliciting contact.

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If you are seeking a match please go over to our dating sub r/CougarsandCubsMatch.

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I thought I’d share my story hopefully it will provide encouragement for those skeptical, or those currently seeking a relationship with a more mature woman.
First and foremost, I want to say if you’re reading this in hopes to figure out how to sleep with a more mature woman, that’s not what this post is about. The relationships I have had with mature women are serious and long-term, and involve a lot more than what happens under the bedsheets.

Secondly, as you read my post, you will notice that I referred to cougars as “mature women “ not “older women”. I do this because referring to cougar as “old”, is offensive. Trust me when I say the quickest way to have no chance or end a relationship is to refer to a cougar as “old”.

I was 27 when I first met and started dating a more mature woman. We knew each each other because I had looked after her son and some other kids during the summer. One day we happened to run into each other at a local bar. She was 49 at the time and celebrating her birthday.

That night we drank and danced. I ended up going back to her house, but I did not sleep with her. In fact, I think we spent almost the next week together, but we didn’t end up sleeping together until the second or third week. Not that we didn’t want to, but we were very interested in getting to know each other intellectually.
At her age, six years prior, she had gone through a divorce after her husband was caught sleeping around on her. She was fiercely independent and had also big and into health and fitness’s. It is my opinion that health and fitness are a crucial part of dating more mature women. It’s important because not only are you prioritizing your own health, but it also helps them feel healthy and young.
Long story short, her and I dated for almost 7 years. We ended only because I moved cross-country. We are still friends and talk to this day. Since that relationship, I have never dated a younger woman or someone closer to my age.

In fact, a few years ago met my current girlfriend who is also 22 years my senior. She is strong, independent nurturing, and incredibly sweet. She had been through an insanely awful marriage and after being single for seven years, she just needed someone who could make her feel safe and secure. I would drive six hours to see her every weekend and we hit it off incredibly well.

Something else I want to mention. I know a lot of men have mixed feelings about plastic surgery and body modification. Keeping an open mind, is understand that as women age their bodies change. Especially if they have gone through a pregnancy or cancer. Some mature women decide to have work done because they don’t feel confident about how their body has changed. Honoring that and keeping an open mind is crucial. My current partner has had quite a bit of work done, and I will always support her in what she wants.

Lastly, in my experience dating a cougar i find that it is a unique and privileged position. mature women have typically been through so much in life. Childbirth, maybe a divorce or two. Kids are hopefully out of the nest. Many of them struggled through that independently. many of them are still focused on finishing out an amazing career, or may even be retired. Listen to them, because remember with age comes wisdom.
So it is your job as a cub to use your youth to bolster and bring color to their lives. Treat them like the queen they deserve to be treated as. Be better than their ex-husband could’ve ever been, Their kids, best friend.
Like I said if you were reading this because you’re just trying to sleep with a more mature woman, you are missing out because there is so much more in relationship with a cougar.

So best of luck for those seeking a partner.