Why Dating Over 40 Feels Like a New Challenge

After a 20 year marriage I found myself suddenly back in the dating game. After a few horrifically failed dates I realized that the dating world has changed drastically. I no longer was able to gauge a man's interest level immediately, I was no longer able to tell if a guy wanted me, found me beautiful or interesting. Men were guarded now; hell, I was guarded! Each date suddenly felt like I was starring in Groundhog Day. The conversations were all the same... Why you're single, what you do for a living, kids, pets blah blah blah.

I plugged along and read anything I could get my hands on from how to flirt to "Why Men Love Bitches" (yes, this IS an actual book!). I tried all the flirting techniques, "dating rules" and the other garbage to no avail. Friends offered their advice: "You have to put yourself out there if you want to find someone" or "It will come to you when you stop looking." Really? How can you do both? I found single friends telling me how to "play the game". (Well, if it works so well why are YOU still single?)

I found men confusing and felt many were sending mixed signals; maybe it would be random texts then I may not hear from them for days. I may see them 3 times one week then not for another 2 weeks. I wanted consistency, I was tired of the games and the "chase". After a while I decided I was just going to be who I was: a single mom who loved beer, wings and sports who is more comfortable in flip flops and a ponytail than heels and makeup. Dating hasn't become any easier but I feel better about myself walking into a situation knowing that I'm being authentic and that if a man is interested, it will be the real me he likes.


Most Helpful Guy

  • Dating for women over 35 sounds a lot like dating for men under 35... so now that you've come to appreciate the struggle, please share that little nugget with any daughters you have...


Most Helpful Girl

  • hey, i am in this area of life its all new to me the possibility of proper dating because initially in my flush of single life i just had fun usually with guys quite a bit younger which is cool because they werent serious and neither was i, now im a bit bored im not looking for a relationship concept that will evolve into us living together but perhaps a partner who i would see on a regular basis. some new thoughts I've been having are like when we were all younger your starting out looking for a future partner usually a potential mother or father to our offspring settle down with and build a life but here we are now, grown up had the kids, self sufficient, settled in our ways, financially secure and pretty independent. so im thinking we are then going out meeting guys who are the same and getting middle aged settled and the drive a man often has when younger has no purpose for us and them at this point. I've met some guys who i do get on with but they often say they dont want anything serious... like whats the point... the fact that both us women and men of our age group can easily get casual encounters with people especially younger ones because of societies less moral outlook upon this, leaves us all a bit out there in a new world. i also feel we have matured and have very well rounded characters and beliefs which make it a little more tricky when combining with a new person whereas when we are younger we have more fluidity about us to evolve together. so i have these thoughts i still have no clue as to what to do or think or respond to them, or it but its a start i suppose lol xx would love to know your thoughts? xx

    • getting bored of your boy toys, hein? :P

      "im not looking for a relationship concept that will evolve into us living together but perhaps a partner who i would see on a regular basis"
      on a non-sexual base I guess? because the other one should be no problem finding

    • Show All
    • I want a best friend I can sleep with :)
      Honestly I want a man that is willing to take time getting to know me before anything sexual happens

    • And yes my goal is to be married again. Not today, not tomorrow, next week, next month nor next year but someday :)


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What Guys Said 3

  • You're right though. In dating, everyone gets more suspicious of the opposite sex as you get older. On top of that the dating pool has shrunk.

  • Now that you're over 40, would you date a guy who's 18 to 30?

    • Me personally... I don't like to go more than 10 years younger. I don't wish to be with someone close to my children's age

  • Hell dating in the 20s is difficult but i can only imagine its harder as you get older.


What Girls Said 2

  • I think how we meet people to date is more a challenge for me than my age. Do not get me wrong, my 43 year old bodied is envying my 26 year old body or even my 38 year old body. lol!

    But I think online dating (edating) makes it harder. When men asked me out in person before online dating, I had the benefit of knowing they actually wanted to date me. They were interested in me. I knew this by the very fact that they asked me out. lol!

    With edating, it is a numbers games, a profile game and then a very awkward game of meeting a stranger for the sole purpose of deciding if you may be interested in dating this person. Incredibly awkward and uncomfortable for me. I hated edating.

    But if you want to have a relationship again, I do not know what the alternative is other than putting oneself out there and doing it. :(

  • I was married for 22 years. The dating scene has changed so much. What I learned... set up some guidelines for yourself and stick to them.