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She’s Out of Your League: No, Go for It

by Ray Gregoire

Have you ever said to yourself, "He or she is out of my league?" Well, that's not true. You should go for it.

Dating in High School

Growing up I had a friend; let’s call him Bill. Bill was not very attractive, having a bad case of acne, but Bill always dated the most beautiful girls. One day, I asked Bill (I was 16 at the time) how he got dates with all those hot chicks. His answer was a big surprise, and here was his dating tip: He just picked up the phone and asked them out. His theory was they were so pretty, guys were afraid to ask them out of fear of rejection and the prettiest girls seldom had dates.

I immediately applied Bill’s philosophy, and ‘voila,’ I had dates with every hot girl in town. Of course, the first dates only lead to a second date if I showed sincere interest in the young lady.

Online Dating at 59 Years Old

I got married and suddenly 38 years later I found myself a widower at 59 years old.

Fear of being alone took hold, and I felt I must start dating soon. My mind quickly went back to Bill’s philosophy and I signed up on Match.com, where I found thousands of available females.

I immediately picked the best looking ladies and sent them emails. I knew I could get a date, especially if I could talk to them on the phone or, better yet, could meet them in person. Little did I know at the time that many ladies used very old pictures on their profiles…this is a ‘no no’ in my book, so many first dates were last dates. I had maybe 20 of those dates.

Looks Aren't Everything

I did manage to date the three loveliest ladies on match.com, all of which actually looked even better than their online pictures. Of course, looks aren’t everything, and I soon discovered that lovely lady number one was a serial dater and number two was a certified nutcase.

I Met My Wife on Match.com

That leads me to number three, Christina, the creator of Boomerinas.com.

It was Sept 23, 2003 and I had arranged to meet Christina at the local Starbucks. When she walked in I almost fell off my chair. She looked like a supermodel and here I was in shorts and a T-shirt. I immediately said to myself, “This is it. Let’s see if you are as good of a salesman as you think you are!"

Our initial conversation revolved around a book she was writing on “Online Dating.” Was I just a research subject? I immediately became very supporting about her book and offered a lot of advice about a man’s perspective on online dating. We talked for two hours and she had to cancel her 5pm date (good work on my part). No games here on my part. I asked for a dinner date on Saturday night and the rest is history. We got engaged 3 months later and married 8 months later.

The moral of the story is, “ She’s never out of your league.”

More Articles for Baby Boomers:

Is This True Love and Will it Last?

Internet Dating Tips for Women Looking for Men

Graphic Floral Print Trend for Summer

Hippie Wedding Dresses for a Casual Bohemian Chic Celebration

What do you think of this article? Leave a comment at the bottom of the page. It won't show up until I have time on my hands... could be a while... hope not.

Ray Gregoire is a retired executive from Johnson & Johnson.

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  1. Christina Gregoire

    Yep, that's what happened. I knew Ray was trying really hard to "sell" himself and it was so endearing that he was hard to ignore. And...Ray was right to worry that he was just research for my book. I picked three random guys (who had contacted me) and I was using the info to write my book. So, ladies, as long as you keep it safe, you meet in a public area, and you don't let the guy know where you live (or your last name), you can have a quick coffee date with almost any man from match.com or any other online dating site. But, you have to use your intellect and you have to be reasonably careful. Match.com has a list of common sense precautions. Read it before you even write your profile.

  2. Brenda Reeves

    If men were honest, looks are everything. If women were honest, money is everything. That doesn't mean we end up with either one though.

    • Raymond Gregoire

      Yes looks do matter especially to men I confess. I don't think money was a factor but I do plead quilty to "looks" being important especially because my wife looked like my teenage fantasy girl "Doris Day”