Finding Love Again: Dating in Your 40s After Divorce for Men

Divorce, especially after a long relationship, is soul-destroying to a man. It is the second most stressful thing someone can experience, only preceded by the death of a spouse or child.

Regardless of whether you or she initiated the split and whether it was an inevitable conclusion or the divorce papers arrived on your desk unexpectedly, this is going to be a trying time in your life.

Your heart will be broken, your mind in a bewildered daze, and your brain self-incriminating, insisting that you’re the most worthless piece of human flesh ever to set foot on this earth.

And that’s just you…

The world will be there too: casting harsh judgments, indulging in quiet assumptions, and, most painful of all, making some accurate accusations.

The likelihood is you did screw up. If you weren’t the primary perpetrator, you were a contributor.

So, where do you go? How do you respond?

Do you let this sink you and retreat into your cave of misery and self-flagellation to remain a hermit for the rest of your days? Or do you bandage your wounds, set your shoulders straight, and set out to get right what you failed to do the first time?

Throughout my ten-plus years as a men’s dating coach, I’ve seen men whose lives were in shambles after a divorce lead the most successful romances. Research suggests that a divorce in your forties or fifties will likely result in a quality second relationship.

Divorce, while it can break any man, is often a valuable teacher.

But what does it mean to set out once again? How are you going to avoid what screwed you over the first time? You’re old now–how do you start dating in your 40s after divorce?

Reentering the dating scene after divorce can be a nerve-racking experience with scary potential for further heartbreak.

This article aims to help you navigate this strange new world’s pitfalls and booby traps, figure out what works and doesn’t for you, and ultimately equip you with the tools to “get it right” this time.

6 Tips for Dating in Your 40s After Divorce

First, welcome to the world of adult dating.

You are at a stage where you know exactly what you want and who to stay from. You know what it means to love and be loved. You know what you consider valuable in life and what is meaningless to you in love and relationship.

Here are six valuable tips for dating in your 40s after divorce.

1. Take the Time to Heal Emotionally

The prerequisite to dating after divorce is healing.

If you’re looking for a new love but haven’t taken the time to heal from the wounds of an old love, the new love you’ll find will be twisted and tainted by the fears and baggage you’ve brought with you from your old love.

Do your healing world, whatever that means for you. Here are some of the best ways to heal after a divorce:

  • Get a relationship coach: The advice of family and well-meaning friends can only go so far. Getting the advice and counseling of a trained and seasoned men’s coach with years of life experience in the field can be instrumental in your healing journey. Too many men, ignorant of their weakness and the strength of the foe they’re facing, try to take on their loneliness and the wounds of their previous marriage alone. Don’t be that guy. Men need men.
  • Invest in other areas of your life: If your marriage was the centerpiece of your life, you would need to find other things to fill that position. Invest in your job or your children like never before. Become the best at your profession. You couldn’t be the best husband, so become the best dad in the world. Finding other things to invest in can distract your mind and give your heart time to heal.
  • Find new hobbies: Trying new things, especially at this time in your life, has massive power. Learning a new sport or getting into the gym can be fantastic ways to get your life back on track after a breakup.
  • Be social: Getting yourself out of your house or apartment and into the world can have a staggering effect on your mental state. It can rejuvenate your mind, distract you in the most challenging times, and give you a valuable perspective that cannot be gained behind closed doors with anything more than your thoughts and misery.
  • Let yourself be sad: While you should tend to your mental state and find ways to enjoy life, the most important part of healing is understanding that you must be sad. Allowing yourself to be sad is the key.

2. Adjust your Standards

This doesn’t mean raising or lowering them. This means changing them.

Your marriage failed. You now know something you didn’t–you know what not to do. You know what sorts of people to avoid. You know what works for you and what doesn’t.

Before you reenter the dating scene, you should update your list of what you want and don’t want in potential partners.

Too many men plunge headlong into dating without taking the necessary time to reassess themselves and their situation and fully understand what they are looking for in a prospective match.

3. Conquer the Fear of Being Alone

Loneliness, or the fear of loneliness, drives men to do stupid things. Before entering the dating world after a divorce, you must conquer your fear of being alone.

If you fear being alone, you’ll chase the wrong sorts of women, jump into unhealthy relationships, and end up more miserable than you were, to begin with.

A man who’s just come out of a divorce needs time to heal. He needs time to think. Once you do start dating, be cautious and patient. You won’t find love right away. Give it time.

Dating in your forties or fifties can be easy and rugged. On the one hand, since you have more of an idea of what you’re looking for, you don’t have to do nearly as much second-guessing or wondering as you did in your younger years.

But on the other hand, because your tastes are so particular, it may be some time before you find what you’re looking for. Be ready for a patient journey.

4. Don’t Underestimate the Value of Independence

Never underestimate the value of independence.

Many men drastically undervalue independence in their quest for a new connection and yearning for love.

Some men prefer to move into a new relationship a matter of months after their divorce, and others wait several years.

While neither way is better, I’ve seen guys have the best years of their lives between relationships simply because they recognized the value of this time.

It is a rare thing indeed for a man of forty or fifty to find himself free of the responsibility of another human.

Tour the world as you’ve always dreamed of. Climb that mountain or get into hunting as you’ve always wanted to. Take this time to work on your hobbies and invest in yourself.

While a healthy relationship is incredibly valuable, the intermediate time between two relationships can never be overvalued.

5. Don’t Neglect your Kids

If you have kids, don’t forget about them during this time.

When I say that, I mean three things:

  1. Don’t forget to care for them: Divorce is one of childhood trauma’s most common and damaging forms. Make sure you tend to the mental states of your children, ensuring that they understand an age-appropriate amount of what is going on but keeping them away from the painful parts.
  2. Don’t introduce them to your new girlfriend too early: It’s good to stay open with your children regarding many aspects of your life, but your romantic life following a divorce is not one of these things. For many children (especially young ones), understanding that Daddy could be with anyone other than Mommy is difficult. It is generally agreed that you should wait between six months and a year to introduce a new serious relationship to your children.
  3. Don’t hide their existence from dates: If this isn’t obvious, don’t hide your children’s existence from prospective partners. Your kids are your life. Include mention of them on dating profiles, bring them up on first dates, and do whatever else you need to do to make it clear to potential partners that your kids and you are a package deal.

6. Be Open

The likelihood is there are things you don’t know. You’re a new fish in this dating pool, and you don’t know the lay of the pond.

Dating apps and online dating are changing the romantic shape of our world (in good and bad ways). You’ll likely have to fish some foreign waters to find this new relationship.

Be open to doing things you would never have done in your twenties. It’s likely that in your twenties, you didn’t have a fraction of the resources you do now. You have the money and the dating apps now.

Don’t be afraid to get outside of the local dating circle. Explore the possibilities of dating apps. Make a few mistakes. Find out what works for you.

Be open to the possibilities of an advancing world.

5 Most Common Mistakes To Avoid When Dating in Your 40s after Divorce

While dating in your forties after divorce should be fun, there are a handful of mistakes you should avoid if you want a successful, serious relationship.

1. Moving Too Quickly

Many men move too quickly when they reenter the dating pool (or enter too quickly altogether).

They plunge headlong into this tantalizing world of novelty and potential in their eagerness to throw off the chains of their past relationship and find a new person.

Here are the most common ways men move too quickly and why they do it.

  • Entering the dating pool too quickly: While there is no hard and fast rule for when you should start dating after divorce, as discussed above, healing usually takes several months. If you reenter dating in several weeks, you’re likely lonely or trying to fill some void in your life. Give yourself more time to tend to yourself. Do some self-care, talk to a relationship coach, focus on your work life or your children–do something that gets your mind off of her.
  • Moving forward too quickly with a new woman: If you find yourself ready to start another serious relationship after briefly knowing someone, there’s something up. As before, you’re probably lonely or looking for some form of validation that the end of your recent marriage robbed you of.
  • Looking for sex too early: While there is no fast rule for hooking up, research shows that the longer you wait to be intimate sexually with someone, the more likely you are to share a quality relationship. If you are looking for sex on the first or second date, you’ve got some inside work to do. Ask yourself why you’re going on dates and what you’re looking for.

2. Moving Too Slowly

While moving too quickly can create massive problems in future relationships, moving too slowly can also be a major issue.

Many men, fearing a misstep in their quest to find love again, neglect to step.

They don’t want to screw up again, so they don’t give themselves a chance. They stay home, play it safe, and let all they could have pass them by.

To be successful in love, you have to know when to wait and when to act. A woman will get confused and lose interest if you wait too long.

Whether it’s waiting too long to start dating again or never being ready to make a relationship serious, moving too slowly can be dangerous.

3. Failing to Move With the Times

Simply put, the dating scene of the modern day is not the same as when you first entered.

The quest for potential dates and future relationships has changed drastically, and while some of it will be confusing, failing to move with the times can be a massive mistake.

Like boomers with the advancement of technology, post-divorce daters tend to maintain an arms-crossed, obstinate air in the modern dating world. They insist that there is one way to find happy relationships, and it sure ain’t on those stupid dating apps.

While this opinion isn’t devoid of reason, and there is a justifiable charm in meeting the ideal partner organically rather than selecting them like a dish off of a menu, a dating site in the right hands can be a priceless tool.

Failing to take advantage of the blessings of modern technology can be a costly mistake.

4. Assuming you haven’t Changed

Simply put, the women your twenty-five-year-old self chased are not the same ones your forty-five-year-old self will be going after.

One of the biggest mistakes guys tend to make when dating later in life is failing to recognize the changes within themselves.

As strange as it sounds, many men will look for love in the same places they did when they were young. They’ll assume that the bar and party scenes are the places for them and dive in headlong.

You’ve changed. You’re older. The women you will want to meet aren’t doing the same things you did when you were twenty. To meet suitable potential matches, you must decide what sorts of women you’re looking for and put yourself in those environments.

5. “Get it Right” Syndrome

One of the most common self-sabotaging mindsets in a man’s quest for new love is fear of failure–more specifically, fear of failing in the same way they did last time. I call this “get it right” syndrome.

I’ve seen this drive the most rational men mad throughout my years as a men’s coach. They don’t know what’s right and what’s not.

They’re afraid to commit–afraid of the word “yes.” Afraid that once they’re in deep and all masks are off, they’ll face the exact issue or situation that drove their last marriage into the dirt.

While fear of failure is completely understandable and (in the right portion) necessary, unreasonable fear of failure is stupidity. It’s limiting. You’ll never know what you missed out on if you always fear what may happen.


So, you’ve traversed the deepest valley of despair, and you’re looking for a way to climb out the far side.

It’s going to be tough, but I’ve got some good news: you know what you want and will likely be ahead of your twenty-five-year-old self when finding a new match.

Before moving into this new and exciting time, you can’t neglect your healing. Healing is the difficult first step of any second marriage.

Once you’ve healed and overcome your fear of being alone, readjust your standards and slowly (but not too slowly) reintroduce yourself to the world of modern dating. Getting back into dating is tough after a failed marriage, but it’s what you need to do if you ever want to move on.

If you are having difficulty during this tumultuous time, it may be a good time to reach out to a men’s coach. Here at knowledge for men, we have a dozen of the best coaches on the planet waiting to help men like you. We’ve got you if you’re tired of the candy-coated vernacular and to-good-to-be-true promises of psychologists and therapists.

Here at Knowledge for Men, we get straight to the point. We know what works and what doesn’t. We’re willing to tell you what you need to do better. We know you want to see the change in your life, and we’re here to help you get it.

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