The Truth About Dating in Retirement

Steve McDonald By Steve McDonald
Bond Strategist

Slap In The Face Award


This week’s slap is another tale from the retirement belt about dating and finding a mate later in life. No, it’s not a repeat of the “nurse or a purse” story.

This is about what some boomers are doing to meet someone to date.

Finding someone for a romantic relationship later in life is a tough climb. First, we have probably forgotten how tough dating is. It can be awkward.

Second, checking out a complete stranger – with intimacy as an end goal – is not what most of us have been practicing for the last 30 or 40 years.

Just the opposite. Although I have known a few folks, men and women, who never gave up the chase.


If you live in a small town, the chances of meeting an eligible person are almost nil. It’s a numbers game, and the numbers just aren’t out there.

Even in big cities, dating can be tough. I have friends who live in Manhattan who say it is almost impossible to meet someone.

So while we would like to rely on word of mouth from our friends, many of us are turning to the internet for prospects. This is where the problems start.

Here are three things that you should not do if you plan on meeting someone online. They’re kind of obvious, but according to what I’ve been reading, it happens all the time.

1. Choose the wrong pictures.

Where did anyone ever get the idea that you can use a 20- or 30-year-old picture of yourself and think the person on the other end wouldn’t figure it out?

Really?! And this is common.

Years back, I had a date with a woman whose picture looked like the description she listed below it: a 40-something. Believe me, her 40s were a long time ago.

We all have bags and sags. If your appearance is all that matters, or if you’re hung up on it and can’t face yourself, move on to another pursuit!

2. Lie about yourself.

Next is fibbing… oh, call it what it is: lying! That’s what the internet seems to be best for.

It doesn’t work any better now than it did when we were 17. If you haven’t done exciting, glamorous things or haven’t been a huge success in the business world, it’s OK.

Your potential mate will find out if you fib or exaggerate, and then you will look like a nut case or so insecure that any healthy person would run in the opposite direction.

Most of us have led routine, work-a-day lives. That doesn’t mean we can’t be attractive to another person. It means we raised our kids and paid our bills as best we could. Any person who has done it knows that’s enough.

3. Go cliché.

I can’t speak for the ladies, but I can tell you, from a man’s perspective, no guy is attracted to or excited by a woman who describes herself as enjoying quiet walks, leaf fights, sharing good books or sunsets together on the beach.

Get real! This is about companionship, fun, maybe travel and maybe sex. It’s not having dinner alone and not being the odd person out (again). If your idea of dating is an excerpt from a light and lovely romance novel, you’re doomed.

They’re out there. They are looking for you as hard as you are for them and, despite what you friends might tell you, the rules haven’t changed. Nice gets nice.

Good luck out there,


P.S. My better half and I are hosting The Oxford Club’s VIP Austrian Investment Experience trip to Innsbruck, Salzburg and Vienna this November 25 to December 2. It’s a great trip with nothing but five-star hotels and Michelin-rated restaurants, and it’s all wrapped up in the beauty and spirit of the Christmas markets of Austria.

Those of you who have gotten to know me at our conferences and meetings will understand what I mean when I say I guarantee we’ll have a lot of fun. And we may just learn a few things too!

There was a great deal of interest in the trip at the recent Investment U Conference in Las Vegas, and we can take only 35 to 40 Members.

So if you’re interested, click here for all the details.

And who knows? You just might meet someone special along the way…