23 Expert tips for Dating an Older Man

Thinking of Dating an Older Man?

This is a must-read for any woman who is thinking about dating a man who is a number of years older than them.

I will tell you what the major obstacles are and the best ways to avoid them.

If you want to make dating an older man work, there are a few vital tips you absolutely need to know.

But you jump straight to the nitty-gritty, it’s a good idea to figure out just why you actually want to date an older man? What is it that you find so attractive about dating a guy who is years older than you?

If you’re like me, you probably first thought about dating older guys when you were back in college.

You realised even then, it wasn’t cool to date guys your own age.

The older guys usually had a car, had money and could take you places you couldn’t afford to go to by yourself.

They appeared to know a lot more than you did and it was exciting!

Ok, so that was all good when the guy was 2 – 5 years older than you, but what about if he is 10 – 20 years older?

Well I can assure you nothing changes..ok so almost nothing.

Even today, if you’re a woman seeking the company of an older man, the excitement will still be there.

You’ve probably dated a few men around your own age and possibly a few ‘toy boys’ as well.

Obviously, if you’re reading this article, that hasn’t worked out too well for you! or you are looking for something different.

So it might be time to explore the option of dating an older man.

Here are my top 23 tips for dating an older man.

Think about why you want to date an older man?

Are you looking for a serious life partner to settle down with?

Perhaps you just want to have fun for a few dates?

Is the main reason because he is rich and you hoping to be spoiled?

Maybe you didn’t have a father figure growing up and you want him to be it.

Whatever the reason, I have always found it a good idea to work out why you want to be in this relationship. Try to figure this out before becoming too involved.

You could be in a period of your life where you don’t want to get too serious. Maybe you just want to see what dating an older guy would be like?

This is a great way to ‘test the waters’ to see if an older man would be a better fit than the same age or younger men you have been out with previously.

If it is to find a partner to spend the rest of your life with then you will be more serious and devoted to making the relationship work.

Some women (mostly young women) deliberately seek out successful mature aged men because they see them as a bank. They hope this man will spend thousands of dollars on them. Clothes, jewellery and expensive trips are usually the most sort after items.

I hate to spoil your dreams ladies but the vast majority of older men looking to be in a dating relationship can spot your intentions a mile away.

If this is the sort of relationship you want (and you are prepared to do what is required to be in one) then perhaps you should be looking for a Sugar Daddy.

Another reason women seek to date an older man is because they have what is often called ‘Daddy Issues’.

This is far more common than you think and it doesn’t make you a bad person just because you didn’t have a great father/daughter relationship.

However, dating an older man in the hope that he will somehow be a substitute for your father is fraught with psychological problems.

My colleagues and I often see many instances where women become very submissive and the man takes advantage of that.

Fine if that’s what you’re into but be sure it is what you want.

Ok, so you’ve figured out why you want this relationship, here are some tips to make it work. 

Always be yourself.

Alright, you’ve seen this older man at work, at the kid’s ball game or during your daily commute and it’s obvious he is interested in you.

The first thing you need to remember is that even though he may know a little about you (or possibly nothing), he has been attracted by who you are.

Don’t try and change into someone you are not. Clearly, he likes what he has seen so go with it. Just because he is older doesn’t mean you all of a sudden change into a different person.

Be who you are and allow it to work to your benefit

Older men often have learnt to accept who they are and apply the same logic to their partners.

You might think you are a bit quirky and maybe even a little strange but that might be what attracted him in the first place.

Many older men like someone who is has a different outlook on life to them and who brings a refreshing new perspective to their lives.

You’ll probably find he actually encourages you not to change!

Older men have had a life before they met you.

Almost all older men come with baggage. (When you think about it, what guy doesn’t!) It might include an ex-wife, children and possibly even grandchildren.

You can’t change any of this so it is best to accept things as they are and move forward, dealing with the issues as and when they are raised.

Some older guys want to talk about their past. They’ll willingly share their life experiences with you so you can get an idea of where they are coming from.

You’ll find his past behavior, in particular how he dealt with major events in his life, a great way of telling whether or not he fits your expectations should similar circumstances arise.

If your older guy wants to know about your previous relationships or major life events, don’t be afraid to tell him.

Revealing a former life-changing event, well into a relationship can cause serious trust issues. Better to lay all your cards on the table from day one.

Older men want to know what you have been through so they can get a better understanding of you and how you think. It helps them to know what types of issues should be avoided.

One thing is for sure, the more he likes you the bigger the effort he will make to minimize the effect his baggage has on your relationship.

Don’t rush things

It’s worth taking a bit of time at the beginning of your new relationship to establish whether your new man is a player or after a serious relationship.

Personal experience has taught me that some guys just want to go out with a younger woman for the thrill or to prove something to their ex’s or their mates at the club.

Older men in particular, like the idea that they can still attract a younger woman. In their minds, it somehow enhances their personal esteem.

Fortunately, they are the minority of the mature aged male population and are also easy to pick.

So assuming you’ve found yourself ‘a keeper’, there is still no need to rush the relationship.

As you would in any new partnership, take your time to get to know your man.

Establish whether this older man has children.

You may already know but if you haven’t asked, you need to.

Before your relationship progresses too far, the issue of children needs to be discussed.

The majority of men who are Dads have ongoing involvement with their children.

His kids will usually play a large role in his life and you need to be aware that sometimes you may need to play second fiddle.

Remember, this will often involve ongoing dealings with an ex-wife or partner.

Ask yourself if you will be able to deal with this situation, especially if you have no kids of your own.

Taking things one step further and depending on the age of the children, are you prepared to be their stepmother?

Then there are your own needs and desires to address.

If you have no children and having them is a big deal for you, remember an older man might not want to have any more.

It is essential you discuss these issues at the very beginning of your relationship.

Finding out what each of you expects out of life in as far as children are concerned is absolutely essential.

Once you are both on the same page with this, you can move forward.  

Don’t be afraid to discuss the future.

Older men have been around the block a few times!

So an older man is more likely to be more forthcoming on his points of view, his feelings towards you and what he wants out of life.

He is likely to know what he wants fairly quickly and you will be the first to know.

He will more than likely just tell it as it is.

Make sure you tell him your feelings and what you are looking for in the relationship.

Despite his maturity, success, and stage in life, it is not all about him.

For this relationship to work, both of you need to understand each other’s expectations.

This is essential to ensuring the relationship doesn’t fizzle out.

It becomes very difficult to make it work when each of you wants different things.

Best to get your expectations out in the open very early in the relationship.

Look after your appearance.

Think back to what you looked like when this older man first saw you.

Were you made up and looking glamorous or were you in your sweat pants and a T-shirt?

However you looked at the time, he liked it, so the important tip here is not to go backwards.

So many relationships fail when the parties stop looking after themselves.

No one expects you to look like you’re going on a first date, all the time.

Just remember if he liked you wearing makeup when he first met you, it would be a good idea to at least make a bit of an effort to wear it whenever you see him.

Similarly, if you keep your weight around the same as it was when you met, you can be pretty confident he will be happy with that.

If this older man of your dreams didn’t shave for weeks, wore daggy old clothes all the time and put on 60 pounds, would you still be as attracted to him?

I don’t know about you but I wouldn’t be.

The added advantage is when you take care of your appearance, it makes it a lot easier for you to remind him he might need to do the same. 

Don’t remind him of the age difference.

Ok, he is older than you, maybe 8 years, maybe 20, but you don’t need to constantly remind him.

Chances are you’re going to notice some signs of ageing in him. The gray hair that wasn’t there yesterday or that wrinkle which has just appeared out of nowhere.

He no doubt has seen it too and it’s probably best not to make a habit of pointing out these things.

Similarly, unless he is incredibly proud of his magnificent maine of hair, referring to him as a ‘Silver fox’ possibly is not a good thing!

(Although some older men do like that expression –  it makes them feel like an animal!!)

If there is a significant age difference between the two of you, other people are bound to comment.

Concentrate on your relationship, not the age difference and ignore people who don’t understand what each of you has together. 

Introduce him to new things.

One of the things I’ve found when dating an older man is that there is often a big gap in wat you have in common.

Unless you have found a really cool, older guy, there is a very good chance you will have vastly different interests.

This is your chance to introduce him to the things that you like. Things that are new to him and that he might find interesting.

Don’t expect him to like everything you show him but if he is keen to pursue the relationship, he will at least be appreciative of your efforts. 

Don’t be childish.

Older men have usually achieved more in their lives and are far more mature than men you may have dated that are your own age.

I can say from personal experience, the older the guy is, the less crap he will put up with.

That cutesy little girl act (with accompanying little girl voice) that may have successfully worked on younger men, won’t cut it in this relationship, girlfriend.

Sure, you are younger and he might expect you to not have the same level of maturity as him, but don’t behave like a child.

Hissy fits complete with pouting and whining will not cut it when you are dating an older man.

If you want this relationship to work, you are going to have to act and behave like a mature woman. 

Don’t let him intimidate you.

Ok, he is older, probably wiser, possibly richer and has been around for longer, but that doesn’t make him the boss of you. (Unless of course, he is your boss!)

Relationships should be 50/50.

You have a right to your opinions, the right to say no and the right to suggest workable alternatives to his ideas.

Just because you are the hot younger girlfriend, it doesn’t give him the right to always get his own way.

Don’t always be a ‘push over’.

Men in general and particularly older men, often will respect a woman who challenges them, often far more than a girl who says yes to everything.

You may not always win the discussion, but you will at least have expressed your point of view and hopefully, he has taken notice. 

Learn from his Experience.

By the time a guy reaches his forties and later, he has acquired significant experience in the ways of the world.

One of the main benefits of dating an older man is that he is able to provide you with real-life solutions to many of your problems.

When he gives his point of view on something, you should listen.

Chances are he has been there before you so he can give you some perspective on the problems that exist in your own life and how to fix them.

He has probably also travelled more than you, likely has a better paying job and has reached a point in his career where he is respected by his peers.

Take all the information he has and learn from him.

Even if it doesn’t work out, you will have gained so much knowledge for your next relationship.

Show some appreciation.

When you are dating an older man, remember there is a very good chance he has been married and divorced.

At the very least he has had a number of long-term relationships.

Studies have shown one of the major reasons men leave relationships or have affairs is because they do not feel appreciated by their spouse or partner.

Fact is, men need appreciation. They want some recognition for what they provide whether it be financially, emotionally or physically.

If your man gives you a gift or does something nice for you, show that you appreciate his efforts by thanking him.

How you thank him will, of course, depend on just how much you appreciated his efforts!

Spoil him in the bedroom.

You’re always going to be younger than him so you may as well use it to your advantage!

Almost all older men find sleeping with a younger woman a major turn on.

There is a good chance you will be fitter than women his own age and possibly a lot more adventurous.

Ok, older men sometimes take a bit longer to get up and running but the plus is they tend to last longer and I’ve always found that worked very well for me!

Ask him if he has a few things that he particularly likes. This saves you having to guess and lets you know what works for him. As long as they fall within your comfort zone, you may already have a head start (pun intended)

Be daring, do things to him that he may never have experienced. Make him crave you! Be like a drug that he just has to have.

If he likes the lingerie you have, suggest he take you shopping and that he can buy whatever lingerie he would like to see you in.

Lingerie shopping might be something he has never done in his life. When he sees how good you look in it, you can be sure he will buy it for you.

As the relationship progresses, just make sure you are getting as much as you are giving. One-sided relationships ultimately don’t work out. 

Make sure he has his finances sorted.

I discovered years ago that older men have a better understanding of personal finance. They tend to have built up a secure asset portfolio.

Even if the ex-wife relieves him of half of it with when she goes, mature age men tend to have the skills and job security to rebuild their fortune.

It’s nice to go out with someone who can pay their own bills and still have enough left over to spoil you on occasions.

There is nothing worse than being told: “I can’t afford to take you out this week because I had to have my car serviced.”

I’m not saying they need to earn a million dollars a year but if you’re going to be in a relationship with an older man, he needs to at least be able to pay his way (and preferably your’s as well).

Be very wary of any guy who comes across as having nothing and expects you to pay for him. 

Dating an older man means you may have to communicate his way.

Older guys have been around the block a few times!

They tend to be better at communicating their feelings than a younger man.

The mature aged man has more than likely reached a point in his life where he doesn’t have to prove anything to anybody. (Except when he is trying to impress you!)

So an older man is more likely to be more forthcoming on his points of view, his feelings towards you and what he wants out of life.

An older man will know what he wants fairly quickly and you will be the first to know.

He will more than likely just tell it as it is.

If you have been dating guys who are shallow and lack honesty, dating an older man who has this upfront approach, might be a refreshing change!

However, you may need to adjust your communication style to be a bit closer to his.

For instance, the modern day texting thing may not be his preferred way of having a conversation. In order to make the relationship succeed, you might want to practice the old fashioned method of real conversation by speaking! 

Partying may not be his scene.

Older men tend to have left the party scene behind.

You will be able to figure out his attitude to partying pretty early in the relationship.

Often the older man’s idea of a great night is to stay home, have a nice meal, a few glasses of wine and spend quality time with you.

Great, you think, but surely not every night!

If you still see yourself as ‘the party girl’ and need that social scene to complete your life, dating an older guy may not be right for you.

His friends and family may not like you.

Family and a guys friends group can be a strange lot.

They have known this older guy that you are dating, for a lot longer than you and they know his history.

He has shown them his relationship weaknesses over the years so they will try to protect him from anybody whom they feel is trying to take advantage of him.

They may see you as a bimbo, someone just after their friend’s money, some kind of trophy, a short term fling, or even a girl with Daddy issues. The list goes on.

If he really cares about you he will do everything he can to reduce the stress his friends and family might cause you.

For your part, take time to engage in conversation with them. Show them that you care about this older man who is their friend and that the relationship you have with him is serious.

Time is the decider in these cases. The longer you are in the relationship, the more obvious it will be to his family and friends that you are ‘the real deal’.

When they see how happy you make him, it becomes much harder for them to hold a grudge against you. 

Respect his work.

Most older men who have a successful career have worked very hard to get where they are.

This was probably one of the things that attracted you to him in the first place.

If you are like me, it is a bit of a turn on to see the respect and admiration he attracts from his work colleagues.

Men in general and older men, in particular, derive a great deal of their self-esteem and confidence from the status they have achieved in their working lives.

Do not try to mess with an older man’s career. Sometimes, no matter how much he cares about you, he will put work before you.

The more powerful a position he has, the more likely this will occur.

If you care about him, give him a bit of space to do what is very important to him.

Remember, it is that hard work and the money he makes from doing it, that ultimately pays for those occasions when he spoils you. 


Dating an older man has many advantages but also a few negatives.

You will have someone more mature, established in their career and possibly wealthier than if you were going out with someone your own age.

He will have more life experience, probably be a bit more laid back and more than likely, have an innate desire to take care of you.

Not to mention he will have solutions to your everyday problems because he has been there before you.

On the other hand, he may be more fixed in his ways, be a bit more controlling (although some women love men to make all the decisions) and he may not want children.

If you look at all the points made in this post, there are enough issues raised to enable you to make an informed decision.

Wikipedia explains in great detail why relationships with age differences occur in their article on age disparity in sexual relationships.

Good luck and let us know your experience in the comments below.