Search icon

Dating a Divorced Man in His 50s; The Good, Bad and the Need-to-Know!

Are you dating a divorced man in his 50s and would like some advice? Are you worried about meeting his ex-wife or children from past relationships? Have you just started dating and have already spotted a big red flag?

In this article we’re going to explore the benefits and challenges of dating divorced men over 50. There are benefits and challenges with dating any demographic, but let’s start with the benefits.

Table of Contents

The Benefits of Dating a Divorced Man in His 50s

Divorced men are older and wiser

divorced men are older and wiser

Ah, the foolishness of youth! As younger women, we thought we knew everything. We believed in love at first sight; we searched for our soul mate and rejected anyone who didn’t meet our exacting standards.

You get wiser, and gain more experience as you age. Going through breakups or divorces makes you value relationships in a way perhaps you didn’t when you were younger.

We don’t write someone off because they are not our usual type or because their beliefs and values differ from ours. We realize people are multi-faceted and life is nuanced.

Divorced men know what they want

Divorced guys have been there and done that. So, if they put themselves into the online dating world, they want to find a partner. It is up to them whether that means a casual or more serious relationship.

They have a clear idea of what kind of relationship they want. People over a certain age are straight-talking and forthright in their approach. If you are dating a divorced man, it’s unlikely he will string you along for a few dates. He will be honest with his intentions, which is refreshing.

Divorced men are secure with established careers

By the time we get to our fifties, hopefully, we are happy in our own skin, have a secure roof over our heads and have a job we enjoy. I don’t know about you, but I hopped from job to job in my early twenties until I settled down into this career.

Just because a man divorces, don’t assume he has lost everything to an ex-partner. Nor does it show that he has financial worries because he pays child alimony. Certainly, divorces can get messy with lawyers fighting over assets, but many are amicable and leave each partner with a fair amount.

Divorced men have an open mind

Marriages that end in divorce can leave a complicated situation behind. There might be children involved, for instance. Your ex-partner may still be on good terms with your parents.

When we go through a divorce, we know the effect it has. Divorce makes us tolerant of other people’s feelings. Whether that be children, family members or friends; going through a painful separation can make us empathic towards those caught up in the divorce.

A divorced man knows what it takes for a relationship to work

a divorced man knows what it takes to relationship to work

This may sound counterintuitive but bear with me. If a person goes through life without ever making a mistake, they will never learn anything new. This is the same for long-term relationships.

Very few of us are still married to the first person we met. It is much more common for people to have been through several long-term relationships before finding Mr. or Mrs. Right.

With age and experience comes a willingness to sit down, talk, and listen. We know we might not be right, but we are open to communication.

Divorced men learn from their mistakes

Most men experiencing the trauma of a failed marriage have a better idea of how to compromise. Relationships take a lot of work on both sides to be successful.

Evolution programs us to be impulsive. However, having experienced divorce once, the divorced man in his 50s is unlikely to rush into a serious commitment again. Older men know you have to work if you want a meaningful relationship.

The divorced man is open to commitment

In our culture, we stereotype most men as individuals who don’t want to commit. In reality, men are not against settling down, and none more so than a divorced man.

He has already shown a willingness to commit to his partner. He has proved it before. It might not have worked, but at least he gave it a go. After all, would you rather date someone over 50 who had never been in a serious relationship or a person with experience?

A divorced man is more forgiving

I believe we become more forgiving as we get older. We realize that no one is perfect. Time and experience allow us insight into our failings. Things that bothered us in our youth may not matter so much when we are older.

We also learn that people and partners are fallible. It takes compromise for relationships to work. One mistake or indiscretion doesn’t mean there is no second date. Humans make mistakes and as we get older, we understand this. 

With age comes wisdom and forgiveness. Our values may have changed, leading to a great scope for empathy.

The Challenges of Dating a Divorced Man in His 50s

He may not be over his last relationship

he may not be over his last relationship

There are challenges to dating a divorced man. Divorce takes its toll on people. 

If the separation was not his idea, he may still feel hurt, angry, or even bitter. He may not accept that his marriage is over and is just looking for a distraction. That distraction might be you. 

Be mindful if he talks about his ex-wife a lot on your date. Does he badmouth her? Is he disrespectful to women? Is he derogatory when he talks about marriage? 

Use this tool to check whether he actually is who he says he is
Whether you're married or have just started seeing someone, infidelity rates are on the rise and have increased over 40% in the last 20 years, so you have all the right to be worried.

Perhaps you want to know if he's texting other women behind your back? Or whether he has active Tinder or dating profile? Or worse yet, whether he has a criminal record or is cheating on you?

This tool will do just that and pull up any hidden social media and dating profiles, photos, criminal records, and much more to hopefully help put your doubts to rest.

One huge red flag is his views on future commitment. Does he appear willing to settle down again or is it a deal breaker? How long ago was his divorce? If it was fairly recent, it might be too soon for this guy to be dating.

He may judge you based on his previous partner’s behavior

Some of us have triggers from previous relationships. For example, one guy I dated did not like my dog. In the end, he gave me an ultimatum; him or the dog. I chose the dog. Now I am wary of men who do not like my dogs. I know it is not fair, but it’s a red flag to me. We may not realize the emotional baggage we are carrying. 

Your behavior could remind him of something his ex-wife did, and it is troubling him. Perhaps his wife had an affair, and now he cannot trust his judgment. Maybe he feels you’ll cheat on him. Try to understand his worries and triggers and encourage open communication.

Does he want to take things slowly?

Perhaps the reason he divorced is that he rushed to get married the first time. It makes sense to him now to take relationships slowly. It means he is serious about you. However, a word of caution; there is a difference between wanting to take things slowly and a lack of commitment. Build trust slowly with positive actions.

His children might not like you

It is not unusual for a 50-year-old man to have children. However, no rule in life says they have to accept you. They will probably be in their early or late teens; this is quite a difficult age for teenagers. They may have already formed an opinion of you that is not complimentary. I was a stepmother for ten years and I can tell you that kids can smell BS a mile off.

Be genuine with them; show them by actions, not words that you are serious about forming a healthy relationship with them. Make sure they know you are not a replacement for their mother and that they will always come first with their father.

He may have constant contact with his ex-wife

If you are dating a divorced man with children, he will probably see his ex-partner regularly. You will have to be tolerant of this because maintaining a good relationship with his kids and his ex is important. It might be difficult at first, but ground rules can help. 

For example, his ex should be able to call in an emergency regarding the children. However, he is not responsible for running over to her house every time she has a problem. Yes, they can meet to discuss certain issues but make it clear, this marriage is over. You are his family now. 

He is responsible for his children but not his ex.

He may not want to remarry

We’ve all heard the phrase ‘Once bitten, twice shy’. For some guys, one failed marriage is enough. He may not see the point anymore. Marriage is a commitment, stating solemn vows in front of friends and family.

People don’t marry without taking these vows seriously. He would mean them at the time. Perhaps now that he is divorced, he no longer sees the point of remarrying.

When we marry, we envisage growing old with our partner. Of course, some people remarry, sometimes several times. Just be cautious. He might see marriage as a one-time deal.

He could be in financial difficulties

Splitting up is never easy. Assets have to be divided, custody terms agreed upon, and alimony calculated. They may have to pay the mortgage if their ex-partner and children are remaining in the home. If the man is the highest earner, the court may instruct him to pay his ex-wife. 

Division of property can mean that this divorced man is paying for two homes. He could be strapped for cash or careful with his money.

Either way, money could be an issue. If you are expecting to be wined and dined, this guy may simply not have the means to do so. Of course, we do live in the 21st century and as independent women, we don’t assume that men have to pay for everything. What I am saying is that money may be tight for him right now.

He might want to protect his assets

We can empathize with someone who has lost everything through a divorce. It can leave people with different ideas about protecting their finances. Some guys, if they do remarry, may insist on a prenuptial agreement which protects them. They might feel they cannot afford to lose money or assets through a split or divorce.

Understanding the Divorced Man: Life After a Divorce for a Man Over 50

He could be insecure

Your confidence takes a huge knock after a divorce. Sometimes, it is only when the paperwork and court decisions are finalized you realize how much it has affected you. 

Your partner does not love you anymore. This is the person you decided to spend the rest of your life with. Now you don’t know what to think. As a result, you could transfer these insecurities onto the person you are dating.

He could lack confidence

Divorce is a confidence destroyer if there ever was one. Your self-esteem is shattered and you wonder if you’ll ever find someone to love again. For some, even bad relationships are more desirable than being single. 

If you are dating a divorced man in his 50s, compliment him, laugh at his jokes and encourage his confidence.

He doesn’t know how to date

he doesn't know how to date

Anyone who has been married for a long time will have been out of the dating game for a while. He may be reluctant to ask you out for fear of rejection. Perhaps he worries the online dating world has changed too much for him. He may not take you seriously or not spot the signs you are interested in him.

He could feel like a failure

Divorce is a failed marriage. For whatever reason, he could feel as if he is a failure. Being dumped or splitting up is never easy; for either person. Some people view it as a bereavement. If he wasn’t the person ending the relationship, he will miss the companionship and the habit of living with someone.

Questions to Ask a Divorced Man

Does he want to be exclusive?

This guy made the ultimate commitment once, and it didn’t last. He may well want to hedge his bets before committing again. That’s not to say he is a player, he might simply want to explore the dating field a little. Maybe he doesn’t trust his judgment, which is understandable.

Does he want more kids?

Many of us in our 50s already have children. However, if you are a younger woman dating an older man, children might still be on your wishlist. If he already has kids, the thought of diaper changing and late-night feeds may not be appealing. 

He had his children when he was younger. Maybe he worries about how he would cope being an older dad. 

Is he on good terms with his ex-wife?

If the divorce is recent, he could be processing emotions and analyzing what went wrong in his mind. He could mention his ex in conversations with you without realizing it. I would question whether he is ready for a relationship if he constantly brings up the topic of his divorce or his ex.

Tips for Dating a Divorced Man in His 50s

Now you know the benefits and challenges of dating older divorced men. Here are some tips for dating a divorced man in his 50s.

Let him know you like him

Self-esteem takes a nosedive after a divorce. It’s the same for divorced women. An older man may not think he’s attractive anymore. Men prefer action, and straightforward talk and they like to know where they stand. So, with this in mind, he is not going to notice subtle hints. 

If you see him out and about, say hello with a smile. Ask open-ended questions such as “What was your weekend like?” Laugh at his jokes and touch his shoulder or arm. Give him clear signals you are interested in him.

Give him a compliment

Everyone loves a genuine compliment. Compliments are a positive way of showing that you have noticed and admired something about a person. These words can brighten up a dull day.

So, if you see something about this divorced guy that you like, don’t be afraid to tell him. It doesn’t have to be related to his looks or clothing. You could comment on how hard his job is, or how his garden always looks beautiful all year round.

Ask his advice

Have you heard of ‘white knight syndrome’? The brave hero rescues the damsel in distress. These stories have been around for centuries (Sleeping Beauty) and are still present today (Pretty Woman). What they all have in common is that a woman needs a man. 

This may make you want to spit your espresso out in anger, but there’s something hard-wired into men that makes them act in this way. So, ask for his advice or help to solve a problem for you and activate his white knight's DNA.

Be a positive person

No one wants to be around a miserable gut, but how many of us think about what we are saying when we meet new people? Do we always complain or moan about life? Or are we cheery and positive about the future? Positive people are attractive to have around. We are drawn to their energy and their outlook on life can inspire us.

Be passionate about your passions

Have you ever met someone so enthusiastic about a topic they infected you with their excitement? That’s the thing about passionate people, it rubs off on others. Whether it’s true crime fiction, science fiction films or countryside hikes. Let him know what you love doing in your spare time.

Be clear about your interest in him

Sometimes you have to state the obvious. We know that guys like straight-talking and are not too good at picking up on subtle hints

As a woman, you may feel as if you are coming on too strong if you say you want to see this man again. But remember, he’s in his 50s, he’s been married before and he’ll appreciate your forthrightness. You can be obvious at the end of a date by saying “I had a really fun time with you, what are you doing next weekend?”

Encourage him to be open and honest

encourage him to be open and honest

Look, none of us is getting any younger. Wouldn’t it be great if we could just say what we are thinking without being judged or criticized? Perhaps there are some off-limit topics you couldn’t discuss with your ex and vice versa. Maybe he is used to being gaslighted and is afraid of speaking up for himself. 

Let him know that this relationship can be different. If there’s a problem, talk about it. For example, if you are in a bad mood, tell him, but add that it has nothing to do with anything he has done.

Be kind and compassionate

I think kindness gets a bad rap these days. If you say that someone is kind, people infer that you are talking about a boring person that won’t say boo to a goose. We underrate kindness and compassion, but as with the white knight syndrome we talked about earlier, women who are caring and loving attract guys who are looking to trust again.

Use body language

For those of us who are not good at flirting, here are a few tips you can use without feeling like a complete idiot. Mirror his body language. For instance, if he is leaning against a wall, you lean as well. If he has one arm on the table, pop your arm on the table. 

We gravitate to people who are like us, so by mirroring his movements, you are subconsciously telling him that you two are similar. Stroke your hair or twirl locks of hair around your fingers. Stir a drink with a swizzle stick whilst looking him in the eyes. Make long eye contact (more than 4 seconds). Touch his knee, shoulder, arm while laughing at his jokes.

What do divorced men want?

I cannot say what all divorced men want, but generally speaking, if someone has experienced a divorce or separation of any kind, they want to be able to trust again. I would imagine that trust, kindness and honesty are at the top of any divorced man’s wishlist. He wants to regain his faith in love and romance again.

How to approach sex with a divorced man

Be open and honest about your needs and ask him about his. Don’t make assumptions because of a divorce. For example, that he lacks skills or that all he wants is sex. 

I find it refreshing when someone is upfront about their sexual desires. He may follow a tried and trusted method that worked with his wife. If that doesn’t work for you, gently nudge him into the things you like.


What does a divorced man in his 50s struggle with?

A divorced man may have trust issues moving forward. Bitter breakups can make a person less willing to open up in the future. Separating from a loved one is much like bereavement. As a result, divorced men may rush into a new relationship because they are lonely.

Is it worth dating a divorced man?

Of course! Otherwise, you are dramatically decreasing your percentage pool of potential partners. There’s nothing wrong with divorcees. We are all individuals with our backgrounds and history. If you like someone, don’t let their divorce put you off.

What percentage of men in their 50s get married?

Marriage rates depend on gender, race, economic and educational status, plus many other variables. Typically, men and women marry in their 30s. If a man gets to his 50s and is not married, he is three times as likely to stay single. If he had been married before, only a quarter would tie the knot again.


As more marriages end in divorce, it is highly likely that when you reach a certain age, you may date a divorced man in his 50s. Remember, relationships end for various reasons. Don’t let an amazing man slip away because of his divorce. Start dating, have fun and forget the old stereotypes.

Utilize this tool to verify if he's truly who he claims to be
Whether you're married or just started dating someone, infidelity rates have risen by over 40% in the past 20 years, so your concerns are justified.

Do you want to find out if he's texting other women behind your back? Or if he has an active Tinder or dating profile? Or even worse, if he has a criminal record or is cheating on you?

This tool can help by uncovering hidden social media and dating profiles, photos, criminal records, and much more, potentially putting your doubts to rest.


Join Our Newsletter

Receive weekly tips & tricks to improve your love life.
Success! Now check your email to confirm your subscription.