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The Pros and Cons of Dating as a Boomer Woman

By Andrea McGinty August 25, 2022 Dating

So, you find yourself single, a bit distant from your twilight years, but not exactly in your 30s or 40s. I can tell you as a dating coach for over 30 years, there are good men out there. Why? I get to meet them every day!

Perhaps you have been married for 30 years and suddenly end up divorced. Or like me, married for 25 years, divorced, but wasn’t quite ready to date with an ailing father and two teenage daughters. But, three years later, now the excuses are gone!

Whether you are just in your 50s or hitting 65, the dating world can be a scary place. It’s new, we didn’t grow up with it – after all in the 80s and 90s, what a stigma there was around using a dating service. Plus, popular online dating sites didn’t really hit their stride until around the year 2000. By then, many of us were wrapped up in relationships, perhaps children and marriage.

So How Does One Find Love as a Middle-Aged Woman?

What do you do when you realize you are ‘out there’ again? Footloose and fancy-free, no longer spoken for, no longer tied down, partner-less, SINGLE?

It’s probably not what you had in mind for this stage of your life, but let’s face it, it’s not all bad either. Perhaps you have left a toxic relationship behind; perhaps you just grew apart; perhaps there was more for you to experience and this was just part of your personal journey.

Regardless of how you got there, dealing with being single can be tough at any age but there are pros and cons to being out there again with a little experience under your belt.

Let’s Start with the Positives

  1. When you are in your mid years, you tend to know yourself better. You know what you want, and what you are willing to settle for.
  2. You have probably had a few relationships, or at least a long-term one, and you know what you love and what doesn’t float your boat.
  3. I believe, as older women, we accept ourselves more. We don’t tend to be as picky about our bodies, our personalities, and are more aware of our wants and desires.
  4. We have been ‘around the block’, so to speak, and know we can survive on our own if we need to. We are often more self-sufficient and independent and have established friendships that can sustain us through challenging times like breakups.

There Are Some Negatives as Well

  1. Previous expectations can interfere. I tell my clients that every man you go out with doesn’t have to be your next husband. Once you learn this, you will actually become quite good at dating. After all, a first date is nothing more than an audition for a second date, right?
  2. With over 1400 dating sites in the US, you would think there would be one good match out there, but it’s quite overwhelming to find it. What do I choose? eHarmony, Coffee Meets Bagel, okCupid, Zoosk, Tinder, Bumble, Silver singles, Elite singles… the list goes on.
  3. You may not feel confident putting yourself out there so you do nothing. You think you will bump into a good man at the grocery store or church. But let’s face it, that’s like playing the lottery.
  4. Listening to your married or single friends stunts your dating life. Of course, they are your friends for a reason: they love you. But that doesn’t mean they know anything about online dating strategies!

It’s True That Dating Takes Guts

Dating and being single in our middle years is quite daunting.

When we were younger, it was simple. You see a boy. He sees you. You like each other and go out on a date. Not these days. Not even close.

And guess what? Most of it is good!

A few weeks ago, in my line of work as a dating coach, I had written my 66-year-old client Anna’s dating profile, chosen the dating site and her photos, and posted it all online for her. Imagine her shock when she woke the next morning to 63 likes. What? She called me and said those men were not what she wanted – and how could she possibly read through all these messages and profiles.

I laughed and reassured her, “Don’t worry, those are just likes, not your matches. You and I are now going to find the right men for you based on your criteria using the search engines and algorithms,” which I began teaching her.

We went over individualized messages for each potential date – there is definitely an art and science to crafting good messages that get the response from the men you want to meet. As I told her, a heart or like gets you nothing! Almost at once, she saw what she called ‘normal’ men, and we were off to the races!

Anna now has been on four first dates, two second dates, and has a third date coming up with one of the gentlemen we found for her. Her confidence is soaring as she’s realized, yes, there are normal, terrific single men out there!

In addition to online dating, find hobbies you like, rediscover yourself as a single person. Be kind to yourself. And, when you are ready, go out and date as a social activity.

In the meantime, just enjoy! Every interaction you have teaches you something about yourself. So put on your dancing shoes, get out the glitter, pull out the golf clubs or pickleball paddle, and go out there and have a ball. Let’s face it, half the fun is in the looking!

Do you think there are pros and cons to dating when older? Are there qualities you’ve gained with the years that have helped you with online dating? What are they? How did you cultivate them?

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The Author

Andrea McGinty is the founder of It’s Just Lunch dating service. She sold it and founded so she could help singles navigating online dating. In the 2020s, she knows the best way to meet people is through online dating using a professional coach and specializes in singles in their 50s-70s!

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