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Internet Dating from a Male Baby Boomer’s Point of View

online dating boomers seniors

by Ray Gregoire

Ten years ago, my first wife died of breast cancer. Where do you go to find a beautiful, intelligent 25-year-old professional woman to date at 58 years old?

After contemplating my requirements for a future partner, I realized that the only beautiful 25-year-old professionals were participants in the worlds’ oldest profession, the pay-to-play profession, if you get my drift.

Match.com and Other Dating Sites

After investigating church groups, ski clubs, and biking clubs, I came to the conclusion that in today’s electronic age the internet was the best venue to start my search.

online dating seniorsI posted a recent picture, filled out the questionnaire as accurately as I could, and posted it on match. The search was on and I must admit I had a ball. I would type in the age, body type, education, location, etc. of what my perfect match would be and, voila, hundreds of pictures of ladies meeting those criteria would show up. Sort of like the Sears Catalogue of eligible women.

Most Women Use Old Photos

I soon learned that most women used old pictures and lied about their weight in their bios.

I vividly remember my first coffee date. I walked into a Starbucks in Seattle and looked for the woman I had met online. She was not there. Then I saw an older, heavyset lady who resembled my date a little. I approached her and said, “I think I’m looking for your daughter.” That was the end of that date.

Lesson learned here, ladies: Underplay not overplay your picture and profile. It’s better for your date to be pleasantly surprised versus disappointed. All dates that were made with women who posted deceptive pictures or profiles were our first and last dates.

Dating Tips for Men Over 50

These tips are for men, but ladies should read them, too.

Serial Daters: Be cautious of serial daters who just love to date but have no plans of seriously settling down. I peeked at Match today and found maybe a dozen ladies who were on this same dating site 10 years ago.

match.com online datingToo Many Divorces: Be leery of women who have divorced two, three, four, and in one case, six times, as most of these women are unable to form lasting relationships. You don’t want to start over again at age 75.

Living in the Past:  If your dates have difficult, serious issues or baggage from the past, move on. These women bring their problems up almost every time you meet.

Listen and Pay Attention: Ask questions and listen. It is amazing what you can discover on a 30 minute coffee date. If a red flag pops up, move along.

I had three or four coffee dates a week and if I found a lady with the right chemistry, I would ask her out right away. Then, we’d go out a couple of times, and if there was a major red flag, I’d break it off and start over again. At this age, you’re not going to change them. They are what they are.

Excel Spread Sheet:

Most of the time, we didn’t get to a second date, but I wanted to keep track of who I had dated and what I thought of them. I used an excel spreadsheet to keep track and rated each lady from one to ten in different categories.

  • Appearance
  • Compatibility
  • Intelligence
  • Financial Independence
  • Loyalty
  • Affection/Affectionate
  • Children (Low scores for kids who lived at home or caused problems.)

Then I Met My Wife:

I dated 60 or so ladies in 3 months until I met Tina and we got married 9 months later. She’s not perfect and neither am I, but it has worked out great for the last nine years.

More Articles for Baby Boomers:

Online Dating: Meeting a Guy for the First Time

Why Do People Get Divorced?

Second Marriage Advice for Baby Boomer Women Over 40

Best Cruiser Bikes for Older Women - Baby Boomers

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Ray Gregoire is a retired executive from Johnson & Johnson.

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3 Comments

  1. Wanda S. Maxey

    Thanks for an interesting article with some great advice. Glad that it worked for you.

    Wanda

  2. Debra Lynn

    I really, truly am sorry. I am not trying to bash all men who date online. It just sounded that way. I am up at night, with a bad virus, can't sleep, snowed in with my two cats. No good excuse. And I would like to comment, I love your sites, as I am a size 14 and I wish that I could find pretty clothes, as I just turned 60. I once was a size 22. Size 12 and under is foreign to me. My dad was 300 pounds and weight was an issue in our family. Deb

    • Tina-Boomerina

      Debra,
      You can bash men all you want. Not a problem. I do it from time to time. Try searching for Plus on this site. I have a few articles about good websites with plus sizes in Europe (and US and OZ).
      T