Dating Confessions of a Single Baby Boomer

Dating Confessions of a Single Baby Boomer

I’ve played the dating game and it’s truly a game of chance.  You don’t know which cards you’ll be dealt in the looks and personality department.  Although you might change some of those cards with diet, exercise and a good plastic surgeon and put yourself out there, there’s still that element of chance that you may or may not find your soulmate.  As we age, the game is more of a crap shoot, but there are winners.  I’m not a gambler.  I know I’m mixing games, but I do know that you have to decide whether to depend on chance or get out there and play the hand you’re dealt.

Thousands of literary pieces are available on the subject of dating if you decide to play the game.  I admit I haven’t read them all, but there’s generally a common thread.  I can recommend, ”Dating After 40: Create Your Ideal Relationship Kit” by Rosalind Sedacca, CCT & Amy Sherman, LMHC which includes the book, “99 Things Women Wish They Knew Before Dating After 40, 50 & Yes, 60!” plus a quiz, a journal, ebooks, and a coaching seminar.  You can also get a free ebook, “Smart Dating Advice for Women Over 40: Answers to Your Most-Asked Questions” at, so you can get an idea if this publication is really for you.

However, that’s not exactly what I’m addressing today.  Here are my thoughts on how we handle what happens when a relationship goes wrong.  I feel that when you break up with a partner you experience the 5 stages as grief with a twist.  I’m using a male pronoun here, but this could apply to any gender.

  1. Denial-No one could leave someone as loving and caring as me. He’ll be back when he realizes what he lost.


  1. Anger-How can he be so stupid? I’m awesome.  Then thoughts of untraceable revenge plots start to form in my tortured mind.


  1. Bargaining- Sure we can still be friends. Maybe if I stick around long enough to listen to your problems you’ll realize what a mistake you made.


  1. Depression-What’s wrong with me? Why wasn’t I enough?  Why can’t I quit crying?


  1. Acceptance-He’s never coming back. I’ll get on with my life without him.  I need to cut off all contact.  (This isn’t possible if he’s the other parent of a minor child.)

Once you’ve completed the cycle, you’ll need to decide whether you want to date.  Taking a break from dating is a healthy idea or you may fall into the rebound pit and walk around with the walking wounded looking for someone to take the place of your lost love.  When you do pull yourself out of the mire here are some warning signs for people to avoid.  Remember, even though I’m using ‘he’, I’m referring to either a man or a woman.  Women are alleged to be the deadlier of the species.

Avoid dating candidates who are:

  • married, separated, divorced numerous times, recently divorced or widowed. The first 3 need no explanation and the second 2 need time to heal.


  • caretakers of children or their family members, unless you want to take on that responsibility too.


  • emotionally, mentally, or physically ill. Also, stay away from a person recovering from addictions.   You may think you can save or help him, but you can get in way over your head before you know it.


  • stalkers who know too much about you before the date. Looking you up on Facebook may be fine.  I suggest you do the same and check  to see if he’s a sex offender.  If he knows too much about your personal life, then don’t engage with him online or in any other way.


  • only willing to email or talk on the phone. In order to really get to know him you need to spend time together.  What you see on your screen or hear on the phone can give you a totally different picture of how the person acts or even looks in real life.  How many of you were shocked when you actually saw the person?  It’s all too common for an individual to post Photoshopped photos or one of him when he was younger.


  • living farther away than you want to go for a date. If he’s from another country, he’s probably thinking rich American and the possibility of citizenship.  If he’s not closer than you both care to drive, then how will you really get to know him?  Sometimes you can weed out the insincere by suggesting that he comes to your location, but not your home.  You usually never hear from him again.  Anyone on the internet could also be a catfish, “Someone who pretends to be someone they’re not using Facebook or other social media to create false identities, particularly to pursue deceptive online romances.”-definition taken from


  • tattooed with the name or face of a previous lover. They’re probably never going to get over that one and you can’t compete with a ghost.


  • much younger than you. Men fall for this more often than women, but everyone is susceptible.  After all, it’s flattering, but in the end he may want the parental figure he never had or a sugar daddy or mommy.


  • insisting you to come to his house or hotel room or wants to come to yours. This is really a no brainer.  You don’t want to be alone with a virtual stranger.  Pick a crowded location and make sure he doesn’t follow you home.  Likewise, if you meet someone on a trip remember that after you leave the romantic atmosphere of that foreign locale, the dream may be over for him.  Giving him an email address is probably the safest way to stay in contact unless he’s a hacker.

I ran an experiment with a supposedly free dating site.  After filling out an extremely short profile, I got a message in about 3 minutes from a man in another country.   I immediately blocked him.  The same day I received 3 other messages from men in the U.S..  During the next 5 days I got 6 more messages and 3 flirts.  Some were older than me and some younger.  Some said they wanted marriage and others were interested in sex.  Relocating wasn’t a problem for a few.  Most of their profiles were very short or nonexistent.  I’m not going to subscribe, but it was a thought-provoking test to see the type of man who responded and how many would reach out based on a Smartphone photo and very basic information.

Yes, I once was a hopeless romantic, but I’ve learned that I have to avoid unnecessary risks when dating.  I’ll save my risk-taking for the things on my Bucket List.  Finding your soulmate may be on yours, but be careful out there and guard your body and your heart.  They’re fragile and worth saving for the right person.

Continue your adventure!

Linda Lea

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