Wedding Woes

Bonus: How to date after 20 years

Hi Jane,

I’m a single 47-year-old woman who hasn’t had a date in 20 years. Yes, you read that right. I had two long-term relationships in my twenties that ended badly. So I swore off men for good. Apparently I’ve done a good job at that. I have a rich life with a daughter I adopted 12 years ago and have rarely felt the need or desire for male companionship. But recently, something has been slowly gnawing away at me. I think it’s loneliness. This could be due to the fact that I only have one or two friends that I stay in contact with since becoming a mom. But I think I’m finally feeling the absence of having someone to connect with intellectually, socially, and physically. So how does one like me enter the dating world after having been away from it for so long? Can it happen organically or do I need to turn to online dating? Should I be honest about not dating for 20 years or should I pretend to be a much hipper version of myself?

Signed,

Single So Long

Re: Bonus: How to date after 20 years

  • It doesn't sound like this person is all that go-out-and-meet-people social as she said she only keeps in touch with 1-2 friends. So online dating is probably the best fit and will allow her to weed people out prior to going on dates and dating will be less time consuming and discouraging. 

    Regarding honesty versus pretending to be "hipper" (lol), honesty...obviously. There's no need to blurt out "JUST SO YOU KNOW I HAVEN'T DATED IN 20 YEARS". But being like "yea, I date all the time. That's me! Such a veteran dater." is weird and awkward. 

    Personally, I would just pretend I was going out to drinks with a friend I hadn't seen in a long time and was trying to re-get to know. Less pressure. More natural. Either you decide "this is why we drifted" or "this person is cool, let's do this again".
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    charlotte989875OurWildKingdomernursejsparklepants41
  • Pretending to be anything you're not is never going to work in the long run. Maybe online dating is a good start, or just starting to join activities you're interested in and see if you meet people there. And if the dating history comes up don't lie, but also no need to have it be the first topic of conversation. It's a big deal to you but it likely won't be to other people. 
    OurWildKingdomernursej
  • IDK if it's just me and my friends, but all of the women in my circle who tried online dating after returning to the dating world only lasted a few months and we were all like:


    we seemed to have more luck in going to MeetUps and finding new groups based around interests, that we then found people to date out of.  That way there's already a commonality to connect on and something to do.  Plus, that'll just get her out of the house more in the first place, which might help more generally.

    charlotte989875OurWildKingdomernursej
  • I definitely think she should start with online dating.  It's a great way to suddenly have the potential to meet a ton of people...all who are also actively looking for romance.

    I'll bet she finds she has a lot in common with people who are recently divorced and also haven't been on the dating scene for many years.

    Quite frankly, I don't see many situations...even once a relationship starts...where she'd ever need to be super, specifically blunt, if she didn't want to be.  The first few dates...if the subject naturally even comes up...would be, "Oh gosh, it's been awhile since I dated, so I thought I'd try this online thing (haha).  How about you?  What brought you to Match.com?"

    As things progress and more history is shared, "You know, I had two really bad relationships in my past, though nothing recent.  I've been focused on raising my daughter.  But now that she's left the nest, it's time for Mama to have some fun!"  It's true, it gives the gist, but without a potentially scary declaration like, "Ack!  You're the FIRST man I've held hands with in TWENTY years!!!"

    Wedding Countdown Ticker
    OurWildKingdomsparklepants41
  • VarunaTT said:
    IDK if it's just me and my friends, but all of the women in my circle who tried online dating after returning to the dating world only lasted a few months and we were all like:


    we seemed to have more luck in going to MeetUps and finding new groups based around interests, that we then found people to date out of.  That way there's already a commonality to connect on and something to do.  Plus, that'll just get her out of the house more in the first place, which might help more generally.


    I think online dating is quite polarizing. I online dated for 2 years and had a lot of fun. I think I learned a lot about myself and what I was looking forward. I also met my H and we've been together for 9 years in total. I do think that you have to be prepared that there are going to be some nopes though. I also think that the site you use needs to be right. I tried POF (hell no for me), match and then finally eHarmony where I stayed for the most time and where I met H.
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