Dating Advice for a Man Over 50

Dating Advice for a Man Over 50

If you’re single, the dating advice for a man over 50 is a little different than for men under 50.

Most men over 50 have been married or in a long term relationship, but not all.

Stay tuned to the end and I’ll share a couple tips for men over 50 who’ve never been married and don’t have kids.

Typically, men over 50 are in a different stage of life than those in their 20s to 40s, especially in the following areas…

Career / Money

Other than in exceptional circumstances, like a pandemic, men over 50 usually have their career and finances in order.

As in, he’s got a job he can reasonably rely on to provide enough money to keep him out of the poor house.

If you’re a man over 50 and haven’t got this part of your life on track, you need to prioritize getting this area in better standing.

Ex-wife / Kids

Many men over 50 are divorced and have children or step-children that are a part of their lives.

This means many women who men over 50 consider dating also have young or grown children.

You need to decide if you want to date a woman with children and what that might look like, or if you prefer to date women who don’t have children, which limits your options.

Sex Drive

Biology dictates that as men near 50 their testosterone declines in a noticeable way.

This is normal… but not mandatory. 😉

Testosterone is the primary sex hormone, so when it starts to evaporate, you may feel like having less sex but more cuddles.

But if you’re dating a woman with a higher sex drive, you may want to top up your testosterone.

Testosterone also keeps you from being a door mat.

Hint: Women don’t want a man who’s a door mat.

There’s a test you can do without having to go to a clinic that’ll let you know if you want more testosterone. Details here.

Money Money Money

Whether she’s 20-something or 50-something+, women who date men over 50 expect those fellas to have their career and finances on track.

But as a man over 50, especially if you’ve gone through an expensive divorce, you’ll want to make sure the woman you’re considering also has her finances in order.

If there’s not a huge discrepancy in assets and income, she should not only be okay with a pre-nup, but want one to protect herself.

After all, does she really want to risk her own assets and income if you get into debt or make a bad financial decision?

That’s how you sell the prenup! 😉

Dependants and Independence

If you’re single and over 50, some of the women you may consider dating will have children.

Watch: Should You Date a Single Mother?

But if she’s considering dating you, she’ll also expect that you may have kids and/or grandkids in your life, as well.

It’s always best to explicitly discuss how involved each of your respective families will be in your relationship, to avoid disaster later.

Never assume she’s involved with her young or adult children the way you are with yours.

Discuss, don’t assume!


I know a couple who got together in their 60s, after both lost their long time loves to cancer. #cancersucks

The woman had three grown children and grandchildren and had been a foster care provider for over 25 years until she retired.

The man had four grown children with grandchildren and great grandchildren. He was the go-to babysitter.

His new lady was done with babysitting.

They had to compromise on how to handle it, so he reduced his babysitting to weekends and if his lady wasn’t feeling up for little ones, she’d spend a weekend at her own place.

They’ve worked it out so they can be together without resentment.

Key point: Love isn’t enough! You’ve got to discuss and agree on some unromantic practical things.

Key point: If you want to have a mutually satisfying intimate relationship with a woman, you both have to make each other a priority over all others (except dependent children in your care).

If you date a younger woman who doesn’t have kids, there are other considerations. Watch the video on that.


If you’re over 50 and dating someone your own age, your sex drive is more likely to be on the same page: more cuddle time, less hard core.

But again, discuss, don’t assume!

And if you’re dating or wanting to date a younger woman, you may need to top up your testosterone! Details here.

Extra Dating Advice for a Man Over 50

If you went through a nasty divorce, don’t be bitter, be better.

Not every woman is the Nasty Nelly your ex is/was.

But also, don’t fall for the same crap different deal. As in, don’t wind up with another woman who looks different but has all the same crappy qualities your ex had.

WakeUP2Luv walks you through how to figure this out.

If you lost your sweetheart to Heaven Above, my heart goes out to you; that’s the worst.

Take the time you need to heal enough to be of value to a worthy woman, but don’t get stuck in grief.

Watch: Heartbreak and Lost Love.

Ch Ch Changes

Realize by the time you’ve made it 50 or above, you’re going to be pretty set in your ways.

Not every way, but some ways, and that means older women will be, too.

You’ve got to decide what the deal breakers and deal makers are and compromise on the stuff that’s really not that important.

Again, WakeUP2Luv helps you figure this out.

No one is perfect, but there’s a perfect match for you.

Dating Younger Women

A man over 50 who’s dating a woman in her 30s or younger will need to be more direct with her.

She not only expects directness and certainty, but if you don’t bring up expectations, deal makers and deal breakers, amongst other practical matters, you could be in for a world of hurt later.

What Kinda Things, Anna?
  • “I don’t want kids. I’m getting (/had) a vasectomy.”
  • “I look forward to living with a woman again but only if she wants to sign a prenup—you’d want to be protected in case I make bad financial decisions, too, wouldn’t you?” 😉
  • “I love that you’re fit/slim/dress nicely/wear makeup/whatever. That’s not only important to me now, but it will be forever. Promise me you’ll always __… What’s important to you?”

Hint: If she says, “A man who loves her ‘for who she is regardless of her weight/clothes/makeup etc.’” or something similar, you can jokingly say, “I’d still love yah… but I’d miss yah!” 😉

Do not let her manipulate you into indirectly agreeing to something that won’t work for you long term!

Stand firm!

You could say

  • “Look, you probably want a guy who’s always got a job or isn’t broke, right?” (What woman would say ‘no’ to that!)
  • “Great, so I’m attracted to your personality but also your body/style/whatever. I have standards, too. If my standards don’t work for you then maybe we’re not a good fit.”

Said with zero attachment or bitterness, just casual friendly finality.

You’ll find out if she can get on board with your deal breakers and deal makers quicker if you know what they are and explicitly express them! #WakeUP2Luv

Key point: If she’s a bit older, she’ll have had life and relationship experiences that create deal makers and breakers for her, too.

Key point: No matter how old you are or what age she is, never go for potential hoping she’ll change for you.

The younger she is the more likely she will change over time, but it won’t necessarily be in any of the ways you hope for!

Never Married No Kids Over 50

Assuming you’ve got your career, finances and health in order you, my friend, have the luxury of dating women of any legal age with or without kids without having to consider exes or offspring.

You can remain in a playing-the-field stage as long as your heart and other parts desire.

I call this Stage 1: Testing the Flavours, mostly reserved for men in their 20s. (More on this in my next vlog!)

However, you will likely tire of this stage eventually and want to settle down with a keeper.

Watch: She’s a Keeper IF…!

Again, the best advice for a man in his 50s I can give is to know your deal breakers and makers in advance so you don’t get caught off guard when some sultry princess sneaks up and melts your heart (while hardening your other parts). 😉

Key point: Love and sexiness are not enough!

Regardless of your age or prior relationship status, my WakeUP2Luv program will help you avoid emotionally damaged women and painful relationships by showing you how to…

filter, filter, filter…

for the right woman for you!

Dooo it.

xo AJ


Dating Younger Women:
Dealing with Dominant Women:

Get Your Testosterone Checked!




About the Author Anna Jorgensen

Vancouver dating coach for men who love women! ❤️ (Not PC and not a feminist.)

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