Retirement Transition and Change

“3rd Act Dating” by Patricia Cavanaugh

By May 31, 2011 May 25th, 2023 3 Comments

Romance once again: More knowledge and ease

Several months ago I decided to take flight into the world of dating after many years flying solo.  Boy things have changed!  I found myself both excited and scared as I dipped my toe into the water of possible romance once again.  Oh my, was I unprepared!

Mutual friends introduced me to a new potential partner.  He called and we decided to meet at a local teahouse for our first rendez vous.   He was a little late so I paid for my drink and waited.  We had a good first meeting, with lots of things to talk about and share.  As we parted, I expected that we might set up another date.  But I felt too nervous to say anything.  I thought he was supposed to do the asking.

Days went by without hearing from him.    I knew he was busy but I was trying to be open about everything.  Then he called to ask me to meet him for dinner. I come from a fairly traditional background and assumed that he would pick me up so I was a little taken a back when he suggested that we arrive separately at the restaurant.  Was he being careful of my privacy or was he ashamed of his car?  I checked out my assumptions with my young friends who said this was not unusual. So I met him for dinner, and again we had a lovely evening.  However, when the check came, I was confused and a bit miffed.  I assumed he was going to pay, but he thought we would split the bill.  I told him that I was used to the man paying, but he said in his world everything was always split.

I left that evening surprised at how the dating world had been liberated.  But what were the rules? Nothing was clear.  The gender roles of old had been obliterated while I was off leading my married, then single life.  We parted at the restaurant with no plans for our next meeting. I was pleased when I heard through my friends that he liked me and was interested as was I.

I did research on the bill paying etiquette and found that there is no clear agreement on who pays the bill anymore.  Some men still do and other’s think it would be an insult to the woman to pay the bill… that somehow she would feel beholden or “less than” if she didn’t pay her way.  Wow, this was new!  Clearly it has been a long time since I dated.  Then, my friends told me that I don’t always have to wait for the man to call.  It is ok if I pick up the phone and initiate a meeting.  This was exciting and freeing but awkward for me.

After many false steps and a few stalwart ones I finally feel that my dating wings are on right side up and placed correctly for maximum flight effectiveness. The relationship with the gentleman mentioned above did not take flight but it did prepare me to step into the 21st century of dating with a little more knowledge and ease.  If you are interested there is a local business designed for over 40 dating called Matches that Matter. Check them out.

Do you have a dating story you would like to share?  We would love to hear from you.


  • Meredith Stout says:

    Hi Patricia, I love this personal story and your openness in sharing it. I am sure it will give moral support to everyone testing out the “mature generation” dating world. I happen to love my independent, solitary living, but I remember those adventures well. Thanks for your blog, Meredith

  • Perry C says:

    Loved the dating story, Patricia!
    Very well written.
    A door opener!

    Perry C

  • You know I just decided recently I’m not paying for anything anymore in the dating department. So decided before going out with a new man I told him, look, here’s how I am, I’m not going to share the bill with you, if you invite me somewhere you’ll be paying. That’s pretty much it. I also told him I understood if that was not acceptable to him. It was just fine. I’m done with paying, if he has the money and wants to ask me out then he knows what to expect. I would recepricate in some way perhaps if we have a relationship by taking him out and paying, however, I’m done with the paying stuff. Sounds harsh, doesn’t it? I’m starting a new business and every dollar I have goes into that business so my real situation is what I’m going on.

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