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Men who dated an older woman, what are some challenges and how to overcome them ?

Men who dated an older woman, what are some challenges and how to overcome them ?

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11 Comments

  1. Being less financially stable and independent in your 20’s while the older women is used to established men and expects that out of you in order to take you seriously.

    How to overcome it? Well you can either find an older woman that maybe doesn’t mind being a bit of a sugar momma, at least in the beginning. Or, you could wait until you have a more established career and stable income to date older woman. Or, you could just be satisfied with shorter term less serious relationships.

  2. Two years older so not really a difference, but I think the point still applies that the amount the earth flew around the sun is a dumb way to measure age. I treated her as I would treat my any other equal similarly as I did when I dated a younger girl.

  3. For me when I first started dating older women it was more we were at different places in life and had different tastes usually because of generational gaps. Many had established careers, adult or near adult children and enjoyed music and movies from the 70s and 80s. Most were pretty understanding that I wasn’t going to be nearly as independent as they were and that we would lack similar interests. However, now I’m pretty close to where they are now when it comes to established careers and financial independence so its not a challenge anymore. The generational gap is still there interest wise.

  4. For me was that while dating a 32-year-old woman 9 years older than me, I was expecting a more mature partner and no drama. However, the drama was there and she was not as mature as I expected so it didn’t last long.

  5. This was pretty hard. She was 15+ older than me. We really got along and had a wonderful relationship, we both had decent income and were grad students at the time. Mentally and sexually we were a match made in heaven. Socially? Not so much. I was ok with her friends, got along decently as far as I perceived at the moment. She hated my friends, though. We used to have arguments about the age gap every time we saw or even talked about my friends because she felt insecure about me being way younger than her (her daughter is only 4 years younger than me). She didn’t think we could make it work because of all the social stigma and that’s what ended up being what tore us apart.

  6. I mean when I was in my teens I dated an older woman but we had to sneak around

    Now once I got older, I dated a couple of older women I guess one was I was 25 maybe 26 and she was in her early 40s, casual , but no real challenges outside of maybe not catching a pop culture reference lol

    And even though I’ve dated younger women before I’m 35 now and my girlfriend is 22 , and we love each other and get along great and that’s really now that comes down to, maybe we’re together for the rest of our lives or maybe we break up next week but that’s just relationships sometimes

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