Dating a Divorced Man in His 50s (9 Things To Know!)

So, you’re dating a divorced man in his 50s – or you’re at least considering it.

Good for you, there are a lot of men in their 50s that find themselves divorced and in the dating game.

But it’s certainly very different from being a 20-something and looking for love!

Here are some tips and things you need to be aware of when dating a divorcee in his 50s!

9 Things to Be Aware of When Dating a Divorced Man in His 50s

1. Find Out How Long He’s Been Divorced

You don’t want to jump on the topic, but something you want to know about this guy is how long he’s been divorced, and how many times he’s been divorced.

It’s not a big deal, but it does help you better understand where his head and heart might be right now.

The longer he’s been divorced or separated the better it is, generally speaking. But never jump to conclusions.

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2. Check How Involved He Is With His Ex

If he’s still living with his ex, or if they’re still on good terms, it might be a big red flag.

You don’t want to be the rebound girl, or get in the way of reconciliation. But it might be just that they have kids, etc.

It’s not always a deal-breaker, but it is something to take into account.

You would hope that a guy in his 50s is able to break away, even if it’s amicable, and give you 100% of his focus.

3. Don’t Expect Him to Change Much

There is a saying, “You can’t teach old dogs new tricks,” and this often applies to guys in their 50s who have had things one-way for most of their lives.

If you’re looking for a guy who is going to change his ways, or learn new things, a divorced man in his 50s might not be the best bet.

You should like and accept him for who he is right now, not who you hope he will become.

Of course, everyone changes over time, but drastic changes are usually unlikely.

4. Don’t Rush Him Into Anything

At 50-something, it’s fair to assume this man has probably been through a lot (as I’m sure you have), and might need some time to adjust to dating again.

Give him space, and don’t try to pressure him into anything he’s not ready for – no matter how excited you are to be in a new relationship.

It might take some patience on your part, but it will be worth the wait.

5. Don’t Be Surprised If He Isn’t Tech-Savvy

I know this is a bit of a stereotype and things are changing, but don’t be surprised if a guy in his 50s isn’t quick to respond to texts or keep up with your social media.

Some guys in their 50s might not even own a smartphone, they might have one of those old Nokia or flip phones!

Don’t take it as meaning he’s not interested if he takes a while to reply to your messages, he might just need a little help getting up to speed with your preferred method of communication.

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6. Expect Some Baggage

Everyone has baggage, but when you’re dating a divorced man in his 50s, it’s likely he’s had some life experiences.

That’s not necessarily a bad thing!

He might have some great stories, and life experiences that can make him a great partner and friend.

But it’s important to be aware that he might come with some “baggage” – such as ex-wives, kids, etc.

Just be prepared for it, and don’t be afraid to ask him about his life. It can be a wonderful thing having 50-some years to catch up on, too!

7. Don’t Get Your Heart Set on Marriage

A lot of women want the fairytale ending with a big dress and an expensive ring when they find the man of their dreams, even later on in life.

Unfortunately, that’s not always a reality when dating a divorcee who is in his 50s.

He’s been married at least once, and most men are in a different stage of life in their 50s, and getting married again is not on their agenda.

You never know though, you can’t rule it out for sure!

8. Find Out What He’s Looking For

The best way to answer a lot of these questions is to be upfront and ask him what he’s looking for in a relationship and what he wants from life at this stage.

One of the best things about dating a man in his 50s is that he’s mature and will be more sure about what he wants from life.

I know how easy it is to get carried away and follow your heart, but don’t forget to take a pause and think with your head, too!

9. Don’t Try to Compete With His Ex

Whether he was married for a few months or 30 years, you shouldn’t try to compete with his ex-wife.

They had something that the two of you will not have, but that time in his life has passed.

Plus, there was a reason why the two of them didn’t work out!

No matter what you or he thinks of her or what their relationship is like, focus on the two of you and be present in the moment.

It’s time to see where your relationship goes and to make your own fantastic memories!

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What Do Men in Their 50s Want in a Woman?

It’s hard to say exactly what men in their 50s want in a woman because every man is different.

However, generally speaking, there are some general things you can keep in mind when dating a man in his 50s.

First and foremost, they want someone who is going to accept them for who they are right now – not who they were in their 20s or 30s.

Older men are also not looking for someone to try to change them, they want someone who will love them as they are.

Another thing to keep in mind is that a lot of men in their 50s are looking for a companion – someone to go on adventures with and share new experiences.

They are much more likely to want someone – and they’ll be able to tell – who is emotionally and financially stable.

You never know though, the best thing you can do with a guy in his 50s is to be open and upfront about what you want from a relationship at your stage in life, and ask what they’re looking for.

Good luck!


Image credits – Photo by Joey Nicotra on Unsplash

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