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  • atskitty2
    Assistant Admin
    • Aug 2013
    • 4467

    Dating in middle-age

    Are you newly single and back in the dating game over 40? Over 50?
    What are the challenges you face?

    I was lucky to meet my partner at age 46, and now at 52, I couldn't imagine dating again.

    What I notice with my friends is that they've sort of given up if they're single/divorced. It seems that old idea of getting "set in your ways" is a thing, at least with them. While I do think there's some loneliness there, it seems they'd rather be lonely than try to adapt to having another person around and give up their independence.

    Having grown children and now maybe even grandchildren could also influence your decision. How has that changed your outlook on dating?

  • Wednesday L.F.
    Veteran Member
    • Oct 2020
    • 362

    I’m not single, but I did start meeting new men for various adventures (mostly sexting) about 2 years ago. When you already having a loving partner at home, dating is a lot more fun. Before I met my husband, every bad date made me feel like I’d be alone forever. Plus my self esteem is much higher than it was in my 20s. I know more about what I’m seeking and what I’m willing to tolerate. It’s a much different experience.

    meanwhile, the men I encounter are more polite, make more effort, and are less hung up on physical stuff. A lot of them are divorced, and a few told me they were eager to prove to themselves they weren’t at fault. I’m having a lot of fun.

    all that said, I’m not sure I’d be looking for a partner if I found myself suddenly single. Lotta labor diggers out there, sadly. I’m not that gal.

    Comment

    • open leaf
      Junior Member
      • Jul 2025
      • 8

      That’s such an honest take. Dating later in life does feel different—there’s more independence, more routines, and sometimes less willingness to compromise. But at the same time, there’s also a deeper understanding of what you really want and need in a partner.

      I’ve seen friends benefit from talking things through with a counselor, even before getting into a relationship. Marriage or relationship counseling isn’t only for couples in crisis—it can also help you reflect on what kind of connection you’re looking for and how to build something healthy from the start.
      Last edited by Alison H.; 10-08-2025, 08:59 AM. Reason: No outbound links.

      Comment

      • Alison H.
        WHI Lead Administrator
        • Aug 2019
        • 312

        I haven't been in the dating pool for a very long time, but at this point in my life, if I WAS, I can imagine that I'd value independence to the point where anyone I was dating would come second to myself, if that makes sense?

        I think as we get older, our independence, our routines, and our needs are just different than they were at 20, 25, or even 30. It's not necessarily an unwillingness to compromise, so much as the fact that we know ourselves better and are probably less willing to put up with less BS from others.

        Comment

        • JonnyR
          Veteran Member
          • May 2018
          • 211

          So with me, I've been "single" now for awhile, and I can personally attest that dating is a rough slog, especially using apps and whatnot.

          While I'm sure that women have their own beef with men, my personal beef with most women, at least where I live, is what I'd like to call the "director" syndrome.

          While stating that they want a man to lead, initiate, and protect, etc, they somehow try to take things over, direct, and crap all over whatever a guy is trying to do.

          Case in point, I'll talk to a woman, we have good conversations over the app or text, and then I ask if they're open to talk on the phone, or meet in person to say hello.

          Oftentimes, they'll completely commandeer the entire situation and make it about what they will or won't do -- "I don't ever talk on the phone; I don't ever meet in person without a video call; I don't ever do a video call and only do a phone call"...it's pretty exhausting!

          They are not easy-going and become extremely rigid...I try to meet them where they are and be flexible, but it does get tough.

          Another example is if we do get to the "date" stage, I'll pick a time and place (which women appreciate...they say!), and oftentimes they instead try and change the place, time, day, etc -- so we go from "I'm going to be here on X day, would you like to join me?" and them saying yes, and then coming back several hours or days later with a NEW plan, day, time and something they'd rather do...

          This completely ruins the masculine/feminine vibe, as no true masculine guy likes to be directed, told what to do, or pointed in some direction when he was leading and taking initiative in the first place, only to be contradicted.

          And before you preach about perhaps not picking places that are public, safe, desirable, near the woman's location, yadda, know that I consider all those variables before making the plan to make the interaction as seamless as possible without resistance!

          Anyway, all of this is to say, yeah, dating when folks are more rigid and older is tougher, no doubt!!

          At this stage of my life, I don't think I want or can live with someone else, and if I did ever move in with someone, we'd need separate bedrooms and lots of space. It just is where I'm at in my life, and logistically, makes the most sense.

          Luckily, I have someone in my life (sorry for burying the lead!) who feels the exact same way, and we've known each other for over 20 years now, and have really hit our stride and appreciate each other so much more than when we were younger as a result of all of this!


          Comment

          • jns
            Assistant Admin
            • Mar 2010
            • 8398

            Originally posted by JonnyR
            So with me, I've been "single" now for awhile, and I can personally attest that dating is a rough slog, especially using apps and whatnot.

            While I'm sure that women have their own beef with men, my personal beef with most women, at least where I live, is what I'd like to call the "director" syndrome.

            While stating that they want a man to lead, initiate, and protect, etc, they somehow try to take things over, direct, and crap all over whatever a guy is trying to do.

            Case in point, I'll talk to a woman, we have good conversations over the app or text, and then I ask if they're open to talk on the phone, or meet in person to say hello.

            Oftentimes, they'll completely commandeer the entire situation and make it about what they will or won't do -- "I don't ever talk on the phone; I don't ever meet in person without a video call; I don't ever do a video call and only do a phone call"...it's pretty exhausting!

            They are not easy-going and become extremely rigid...I try to meet them where they are and be flexible, but it does get tough.

            Another example is if we do get to the "date" stage, I'll pick a time and place (which women appreciate...they say!), and oftentimes they instead try and change the place, time, day, etc -- so we go from "I'm going to be here on X day, would you like to join me?" and them saying yes, and then coming back several hours or days later with a NEW plan, day, time and something they'd rather do...

            This completely ruins the masculine/feminine vibe, as no true masculine guy likes to be directed, told what to do, or pointed in some direction when he was leading and taking initiative in the first place, only to be contradicted.

            And before you preach about perhaps not picking places that are public, safe, desirable, near the woman's location, yadda, know that I consider all those variables before making the plan to make the interaction as seamless as possible without resistance!

            Anyway, all of this is to say, yeah, dating when folks are more rigid and older is tougher, no doubt!!

            At this stage of my life, I don't think I want or can live with someone else, and if I did ever move in with someone, we'd need separate bedrooms and lots of space. It just is where I'm at in my life, and logistically, makes the most sense.

            Luckily, I have someone in my life (sorry for burying the lead!) who feels the exact same way, and we've known each other for over 20 years now, and have really hit our stride and appreciate each other so much more than when we were younger as a result of all of this!

            Sometimes an easier solution would be to search for a significant other in places that have more traditional man and woman roles. From what I have seen in Southeast Asia, the roles are more traditional. That is not the only place. I would think that the roles are more traditional in much of the third world. You may have to learn another language, though, so you can communicate correctly.
            I have but one lamp by which my feet are guided, and that is the lamp of experience.
            ...
            Shall we gather strength by irresolution and inaction? Shall we acquire the means of effectual resistance by lying supinely on our backs and hugging the delusive phantom of hope, until our enemies shall have bound us hand and foot?

            From a speech by Patrick Henry on March 23, 1775 at St. John's Church, Richmond, Virginia

            Comment

            • atskitty2
              Assistant Admin
              • Aug 2013
              • 4467

              JonnyR I definitely see this in friends and co-workers. There are so many games, so much jockying for position.

              One of the women I work with is going through a divorce, late 40's, and she's already getting out there on dating apps. She's met herself a man that she's already trying to jerk around.

              Glad you have someone in your life that can be a partner and mutual needs are met.

              Comment

              • JonnyR
                Veteran Member
                • May 2018
                • 211

                atskitty2 Thanks I appreciate that! When you say "jerk around" I was curious what you meant by that? And if you'd talked to her (or perhaps you're not even close enough to) about it and why she's doing it, or more so, why are women doing these things now?

                Is it attachment style? Is it trauma? Is it PTSD from bad dating or insecurities? What the heck is going on here?

                Why are the masculine/feminine dynamics so messed up!?

                Comment

                • Alison H.
                  WHI Lead Administrator
                  • Aug 2019
                  • 312

                  I think part of it might just be the evolution of the female dynamic. Some of it could be related to past experiences, but I think a bigger part of it (for some, at least) is this:

                  They don't NEED a man the way they did decades (or centuries) ago, and have more agency over their lives and what they're willing to tolerate (or not), and maybe more than ever before, they're able to seize what *they* want (versus what society thinks they should want or have).

                  I mean, women couldn't even have credit cards in their own names until 1974. Now, women are taking on a more "male" role as far as having agency over their own lives, if that makes sense. They're working full-time, supporting themselves, buying houses, treating themselves to things they want, whatever et al, and they don't need to rely on anyone else for those things.

                  Which means they're exercising their right to date or "play the game" like men have been for... pretty much forever.

                  But for women who are divorced after a long time, part of it might be sowing the oats they couldn't sow before. That's new, thrilling, and probably to a degree a bit of a power trip. That's not a bad thing, I don't think. I mean, if you were stuck in a marriage for years and years and were suddenly free... I wouldn't be "jerking guys around," but I get the instinct to, from a psychological perspective.

                  And the same might be true for women who had had long-term relationships in the recent-ish past and are single again, I'd imagine, just because they can.

                  Comment

                  • JonnyR
                    Veteran Member
                    • May 2018
                    • 211

                    That's an interesting take for sure! But are men really "playing the game" when they just suggest a place to meet and a time and take the lead?

                    I am ok with someone having agency in their dating life -- all the power to them -- it's that there seems to be a disconnect with what women say they want, vs what they really show they want.

                    Another interesting trend that I see is with the following wording in some shape or form:

                    provider, protector

                    Whether the woman says she wants a man who is a "provider and protector" or explicitly states this in a way that makes me feel a bit uneasy as a true independent and masculine man...

                    It's almost code for "you're paying for everything, and pretty much doing everything I want, and if you can't handle that, don't reply"...

                    It's almost like the sugar dating thing -- there seems to be some type of script or nomenclature that they're getting from somewhere cause it's rampant...

                    Not very sexy or appealing if you ask me!

                    Comment

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