Dating in My 50’s: Does it Get Better?

Dating in My 50’s:  When Did the Rules Change?

I was a late bloomer in high school and really didn’t start dating until college. I learned the rules really well.  I waited for a man to ask me out and I didn’t make the first move.  I would obsessively think about whether someone would call and whether or not “he” liked me, but I never doubted the way the process was supposed to work.  I knew that I was supposed to wait and the men I went out with never questioned that I was a “good girl” with morals and values.  Sure, some would try to push the envelope, but when I said no, they stopped.  I never once felt like my options were limited or that not dating was preferable to dating.  Something has shifted since the almost 30 years I was single, and I am no longer confident that a second chapter is a reality for me.

Since day one, the singular component of my life that confused me was that I became the center of gossip just because I had become a widow.  Five days after the funeral of my Phil, I was told my a man who was the same rank as my husband was, that there was a dating pool going among the people Phil worked with as to how long it was going to take me to date and remarry.  Some said six months and the last date was two years.  At the time, it was offensive since Phil and I were so insular and neither of us put out any vibes for wanting anything but one another.  Now?  I want to know when these men are going to pay me.

Six weeks after Phil had died, I got a glimpse of how much my life had changed.  Couple friendships evaporated and I couldn’t understand why until a woman assumed I was after her husband because he had Phil’s autopsy report and he had come to count Phil’s underwear and socks when those black foot lockers came home.  She took the report to someone who told me that I needed to honor my Phil’s memory.  Really?!  If I were making a play at a man, I wouldn’t give pictures of a dead person.  This singular event bothered me so much that I ran away to Germany to get away from the gossip and speculation.  I wasn’t ready for any of it.

The first time a man hit on me, I was running the first marathon after Phil died.  I am a marathon maniac and as I came upon a man with the requisite outfit, I encouraged him to run on to the end.  He recognized me.  To this day, I will never forget the savage from Maryland who started running to tell me how much his wife didn’t understand him.  He actually said, “I have needs, you have needs, maybe we could….”  That would be a big fat no.  It hasn’t just been him.

I work with a man that many people thought we should get together.  I went out with him one time.  He wanted the Friday Night Special girl.  You know, hide me during the week to avoid gossip or people knowing, go out Friday and get it on, and then go back to work on Monday.  The answer was and still is NO!  Come to find out, this man had a girlfriend and this girlfriend got into his e-mail and has repeatedly e-mailed me as to how I wrecked her relationship.  One date and the word no did not end her relationship.  He just found someone else to have the Friday night on the side fun.  Her name is not Linda.

It is interesting how many times I have heard, “My wife and I have an understanding…”  Well, I am not the on-the-side understanding kind of girl.  Why would I want that kind of relationship?  Why would I cheapen myself to that level?  I think the ugliest aspect of that statement is that it works for some women….I am not her.  I would rather be alone than in  a relationship like that.

I had another man ask me out.  I was actually looking forward to it UNTIL he kept texting me as to what I was going to cook for him and what I cooked well.  I tried joking with him about not being Suzie Homemaker.  His comeback?  He asked who cooked when I was married.  Well, I did for the most part, but I am not her any more and the fact is that while I like to putter in the kitchen, it is my love gift .  It is not a gift that someone who wants to take me out for the first time should be pressuring me for.  Needless to say, we never went out.

Then there was the private investigator who told me that he had Googled me and when he saw how nice looking Phil was  and what his story was, that he felt intimidated and maybe I could help him with that intimidation.  He was a one time very short date wonder.  When he called to tell me that he had a face lift to look younger, I rolled my eyes—No thank you.

I had another man I went out with three times.  He was a man of faith and I enjoyed talking about my faith and laughing with him, but there came a day when he told me that he wasn’t feeling chemistry, but maybe I could help him discover if we had chemistry.  Ew?  Don’t let the door hit you in the tush on your way out.

I went out with another man who made me feel really icky about dating and men to the point that I haven’t dated in six months and we were only going out a month.  He was a taker. He acted normal and he put the full press attentiveness on.  We made plans six months out, and then he shut it off by using words like, “try before you buy” and “going back to an ex-spouse if she wants me back.”  He was the one who cried frequently, but told me that he couldn’t be there emotionally for me and that my strength came across as the sin of pride.  Like I had a choice with the sniveling soft person he was.  He lived in a world of Amish guilt.  Was he Amish?  No, but he lived in that area and he was as tethered to the irons of rigidity as they were, but as bitter as they come in terms of women proving themselves.  This one chipped my self-confidence in many ways because I never saw it coming.  He had a light switch that clicked off overnight without a warning and his words gouged my heart creating a wariness that I never before had.

I decided to try the online dating world.  Epic failure.  First, I am too afraid to meet anyone and the chat rooms turn into a bully fest.  People are mean and it doesn’t matter if it is a Christian dating site (it says it is) or a secular site.  I feel like a piece of meat and that people are shopping for the best piece of meat. The scammers run rampant and I am not convinced that anyone ever dates off of these sites.  The Christian online site was what made me give up ion that mode of dating, also.  Many men wanted the little ladies and had the attitude of the women totally submitting finances, lives, etc. to them.  Both the men and women often stood in judgment against anyone they perceived to be different or that they felt threatened by.  I made it known that I had given up on dating from the online site, thus I did not get bullied often, but cyber bullying is awake and alive on these sites.  I finally had enough of standing idly by, and I  left.  Online dating through any site with a chat room, Christian or not , is not for me.  Online dating is not for me.

I laugh because it is funny, but kind of sad, too.  I haven’t dated in a half of a year.  Would I like to?  Not if my options are Friday night special, try before you buy, Suzie Homemaker, or chemistry- men.  I would rather just wait and hope that one day a man will run into my life and that God will conk me on the head and say, “This one, dummy, this one!”

Tag….your turn.  No names.  Share a bad dating story.  Yours or someone else’s.  No names.  Just fun.  Make me laugh this snowy, snowy day.  I do not get to run, thus shoveling and laughing is all I have.


  1. stayathomegingers says:

    One time I had a date I was actually looking forward to. I curled my hair, did my makeup nice and I even put on a skirt. I hate skirts. 🙂 I showed up to the restaurant on time and in walked a guy who looked like he had just walked out of the gym showers, without showering. He had on a faded, too small blue shirt, black gym shorts and…wait for it…crocks. He wore orange and green crocks. I kid you not.

    I decided to at least go through with the date and by mid-date I was so exasperated with this man (boy-child) that I decided to be as obnoxious as I could so he wouldn’t like me. Turns out he liked that.

    Turned him down for a second date. And he was like “but I think you’re really hot.”

    Mmmmm…thanks. But no thanks

    Never wearing a skirt again. 😉

  2. stayathomegingers says:

    My friends and I now just refer to him as “Crocks”. 😉

  3. In 2005 I met a man and we dated for a month. He worked offshore, and was only home every 2 weeks. He had his 3 kids on his home weeks, so our “dates” included them. (I was more of a babysitter!) I got to know him better, found out his “religious beliefs” were a made up story to lure in women. Things got worse as time went on. Noticed he was an alcoholic and obsessive gambler. When I told him I was done, he said “no problem, women are like buses there is another one every 20 minutes.” I offered to give him the bus fare! Loser!! My last time meeting someone via an internet dating site. No thank you!

  4. This story is hilarious–crocs?

  5. stayathomegingers says:




  1. […] Dating in My 50′s: Does it Get Better?. […]

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