7 Ways to Survive Dating Over 50

7 Ways to Survive Dating Over 50

I’ve been thinking about writing on this topic for a while.  I’m over 50 and single and have a lot of friends in the same boat.  And what I’ve found is that dating over 50 is just insane!  What I thought I knew –and mastered fairly well in my younger years — doesn’t seem to translate into the dating scene of today.  So what do you do when you’re single and want to meet someone interesting and emotionally available?  Or is that really an option for women in midlife?

From Allison over at Women Bloom, dating at 50+ is like a “roller coaster”:

I’ve been known to think finding the right guy at this time in life, online or otherwise, was akin to pigs flying, or a snowball coolly sipping an iced latte in hell.  Just listen to me rant about my recent adventures on Match.com and you’ll see why I might be excused for thinking that.

But, hope springs eternal.  I have a dear guy friend who recently reconnected with a college love interest. It was not to be in their younger days, but they have blasted aside all logistical complications and emotional fears in their late 40s.  She has moved from her longtime home to live with him clear across the country.  Because they are soul mates.  I LOVE that!  Maybe it COULD happen to ME!  

Could it?  Like Allison, I know women who found their soul mates in midlife.  Over at Gen Plus, guest author Dee Frazier agrees that single women over 50 should get back in the dating game but maybe with a different mindset.  According to Dee, dating can actually be fun if we view it as “just a date — not the rest of your life.”

Are you wading around in the dating pool? Are you clueless of what the new rules are and bogged down with fear? Hesitating because the dating game has changed dramatically since you were in your 20s?

Sooner or later­ if you truly desire a relationship ­ you must jump in. Make a big splash. When you decide that you are ready to play the dating game, look at it as an adventure.

The grown-up dating game has never been more interesting and challenging. There are more players than ever before. Why? Because of higher divorce rates, longer life spans, and a greater tendency to never marry. This contributes to more single Americans than at any other time in our country’s history.

The U.S. Census Bureau tells us that of the 97 million Americans who are 45 or older, almost 40 percent ­36.2 million­ are available singles. There is no shame in being single.

How do we get back in the dating game though?  I’ve tried the online experience several times since I divorced.  On Match.com I heard from men who were interested.  But I had to weed through the profiles myself, which actually seemed like work after a while.  Two of the men I agree to meet were 10 years older than their profile age and another had an online picture of himself at least 40 pounds lighter than when I met him.  

Next I tried a site where they do pre-screening — PerfectMatch.com, the site featured in the movie “Must Love Dogs”.  Well I didn’t get the dog or a date.  After hours of completing my profile and their detailed matching assessment, PerfectMatch matched me with one prospect in the 3 months I was a member.

My last experience was with Chemistry.com — the latest, supposedly most inclusive online dating site.  Again I created my profile, put up a decent photo and filled out the personality assessment.  It was funny how many of the prospects Chemistry sent were the polar opposite of who I said I was looking for.  I was connected though with 2 very nice men who shared that they were getting complimentary Chemistry memberships and had been for months.  I inquired about this obvious disparity — women pay, men don’t, but got no clear answer from Chemistry so I didn’t renew.

I haven’t given up on dating over 50 but here are 7 survival tips I’ve learned along the way:

  1. Get informed.

This isn’t the dating scene our younger selves were used to.  By far the best midlife dating primer I’ve run across is an “everything you wanted to know about dating over 50” article by Alisa Miller over at Nerds Do It Better  — and yes they mean that “it”!  There are books, CDs, coaches, courses and any number of other resources available elsewhere.  But save yourself some money and use Alisa’s article to get the lay of the

land as you venture onto the over 50 dating scene.

She includes links to all the dating sites for seniors — which in dating land means anyone over 40 or 50, which really galls me but I digress.  And Alisa gives online and general dating sites, tips for meeting online or not and a full 10 pages of dating resources that are well-organized with all the links.  I have to admit that when I read her article I was amazed that only 3 people had commented — and one was a man!

  1. Have a dating “kitchen cabinet”.   

Francis and Michael, longtime friends and a gay couple, are my dating kitchen cabinet.  Maybe it’s just me but I like to have a second opinion if I’m really interested in someone.  My friends have the ability to see aspects of someone’s personality that I may not.  Francis and Michael are always honest and candid about what they see and if they don’t like my date, they’ll say so.  It’s not that their opinions are gospel, but they do offer me the opportunity to view a date from a different perspective.

  1. Put your best foot forward.

I hate to say it but there’s serious competition out there based on the numbers from the Census Bureau.  For online dating spend time writing a profile that shows you in the best light.  Get a friend’s opinion on the final draft.  And if you don’t have a great photo, ask that same friend to snap a nice candid shot for you to post.

Have a simple and flattering first date outfit already in the closet — like a uniform.  When you have that first date, you don’t have to agonize over what to where, how it fits, how you’ll look.  You’ll already know and be able to head to meet Mr. Maybe-Right with a little less stress.  And the best thing to show on the first date is the real you.  At 50+, who has time for being anything but authentic.

  1. Don’t settle.

I’m not looking for Prince Charming anymore — I went to his funeral years ago.  As I’ve gotten older, my ideal date is kind, smart, emotionally available (did I say that already?), thoughtful and not addicted to any substance other than chocolate or coffee.  Have you made a list of the qualities you’d like to find in the people you date at this point in life?  It helps you get real clear — again — on what works and what’s non-negotiable for you in a relationship.  If someone doesn’t measure up, don’t settle for less than what you want.

  1. Lighten Up

When I was young, I took the whole dating thing so seriously.  As I think back on it, the end goal was to get married and have a family — at least that’s what I learned back in the day.  Now I don’t really worry about getting married again.  So I’m less wedded — not to make a pun — to the end result and more to the journey in a relationship.

I’ve also accepted that sometimes I meet someone who just not that into me.  If you haven’t read the book by that name, it’s enlightening– and liberating.  From Kathryn Lord, the Romance Coach, here are a few signs that a man just isn’t that into you:

He tells you he’s just not that into you.

He tells you he isn’t ready to settle down into a relationship.

Doesn’t give you a hug or a kiss goodbye.

He doesn’t call.

Sound familiar?

  1. Protect yourself in all ways possible.

First, don’t share personal information, like your contact info until you’ve really gotten a comfort level with someone.  For instance, keep your email private which the top online dating sites always do for you.  If you decide to talk with someone on the phone, call them and *67 before you dial their number so your phone number isn’t revealed.

When you’re ready to meet someone in person — coffee in a very public place is a good first date — advise a friend where you’re going and that you will call after you leave.  My sister and I have this arrangement and it works well.  Once I progress to a longer date, like dinner, my sister knows to call at a certain time.  As I answer the call in front of my date, I apologize and jokingly explain how my sister and I look out for one another because my date — and yours — should know that someone cares about us.  

The other way to protect yourself is at the point you decide to take a new relationship into intimacy.  The bottom line is that over

50, we need our own stash of condoms and — no you can’t depend on the other person to have one.  Nancy over at Boomerful, who found herself single in midlife, reports that:

After more than a year of being single, what I have learned is this: Condoms are a fact of life. Don’t consider any other way, unless you are really monogamous and have both been tested. If you are in bed with a guy and he doesn’t have the guts to use a condom … or he tries to convince you that one isn’t needed … RUN. He is not worth a conversation, much less your body fluids and possibly your life.

If you’re timid about buying a box of condoms from your friendly neighborhood pharmacist — it is a weird feeling — then you can buy them online.

  1. Enjoy yourself.

This one sounds easy but I’m not quite there.  It’s a goal I haven’t quite reached yet in this new world of dating over 50.  I’m hopeful, though.

Karen Batchelor

I am Karen Batchelor, genealogist, avid descendant and sometimes skeleton in a family closet. I’ve been “hot on the trail” of my ancestors for 35+ years and make sense of the future from knowing about the past.

August 22, 2008 6:30 pm by extremeancestry in


Karen Batchelor

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