How to Date an Older Man - Cool Dating Advice

How to Date an Older Man

I remember having a conversation with a lady friend of mine about her dating life, she felt men her age wasn’t on her level intellectually or mature enough. She was absolutely tired of dating men her age and was considering dating older men. Plus, she knew I’ve been in a relationship with a man ten years my senior for five years.  So, if I can be in a relationship with a man ten years older than me why couldn’t she? How do you date an older man? Dating an older man has its pros and cons, but that just comes with the territory. If you would like to date an older man I must first tell you to be mentally prepared for it. You mentally need to be ready for more maturity and responsibility he has with his life. Dating an older man is not like dating someone your age or someone younger than you, especially if you are dating an older man that has his priorities straight. If you are contemplating dating an older man this article is for you. So, how do you date an older man?

Please Understand. . .

First and for most I repeat please be mentally prepared to date an older man, because depending on what that man is looking for he’s not up for games. Yeah, some older men may date younger because they may be looking for younger women to bring out their fun side, but at the end of the day that older man has responsibilities. Therefore, he may choose to take care of his responsibilities first before having fun. So that’s something you will have to come to terms with and understand when he says “he’s busy.”

That could be a hard pill to swallow, but a busy man taking care of his responsibilities is an attractive reliable man. That’s why you must consider dating an older man.


You are probably looking for a man that is responsible and reliable right? Good.

When dating an older man understand that his responsibilities may be a lot more than you can handle, unless you have similar responsibilities, like children. When you look at dating older men that may come with children he had from a previous marriage.

It’s not a bad thing that they may have children, just be aware that children may be involved. If that man has children and he loves them dearly, understand he will put his children first. So, if you’re out on a date and there is a concern with one of his children, be prepared for the date to end. Once again, a man that loves his children is a man to adore. This shows that if things get serious between you two, he will love and aim to protect you as well.

Down to Business

We now understand that dating an older man means he has responsibilities and does not have time for foolish games. Now, we must understand those older men like getting down to business, in many ways. Most older men are straight arrows. They aren’t going to beat around the bush. Whatever they desire from you, you will know.

If that man is looking for a serious relationship he will tell you up front.

He may just be looking for a casual date then he will tell you that.

He could just be looking to have some fun in his spare time, he will let you know.

Most men are always looking for sex so you will definitely know this one.

Most mature men aren’t going to lead you on or make you believe a lie. That behavior is manipulative and immature. An older man that knows what he wants will immediately get down to business! How’s that for a “turn on.” Wink* Wink* So, be prepared for him to state exactly what wants from you. And please don’t hesitate to state how you feel, be assertive.

Entertain Him

No, you are not a clown at a circus, but older men love to be entertained. Entertain him in a good way by finding out what he likes to do and doing it. Just because a man is older doesn’t mean he’s boring.


He likes to have fun too.

He will probably be a lot more fun than you, even though you are younger than him. So, what do I mean by entertain? It could be as simple as telling jokes or having a good conversation. Or, if you’re really comfortable with him, wear something sexy and tease him with a little dance before you go out or stay in if it gets a little “hot and tempting.”

Just get creative. He would appreciate the effort.

Give Him Space

The trick is to make him miss you. Leave him alone for a few days, try not to call or text so much or don’t contact him at all. When he wants you, he will come looking.

Older men like to have their space.

They aren’t into the extra clinginess and the constant demand for attention. So, let him call you. Don’t worry, if he truly misses you he will call. Plus, when you guys meet up in person the interaction will be great because you missed each other so much.

Don’t Be A Nag

I’m pretty sure older men have had their share of nagging girlfriends or even ex-wives. This stage in their life they do not want to hear constant nagging or complaining.

Don’t complain about everything because it will get old fast.

When you’re young you tend to be more argumentative and open to confrontation. Older men are the opposite. They are done with immature behavior. Try to get your point across with mature and effective communication because nagging is not going to do it. This could drive him away.

Listen To Him

If I know anything about older men, I know they love to talk. So listen to them, they have a lot to say.

Older men have a lot of stories they can tell you about themselves from their childhood to their adulthood. You can learn a lot about them just by listening to them talk. If you just let them talk they will tell you everything you need to know, no need to ask them tons of questions.

Since they have so much experience in life, you could learn something from them. Since I’ve been in a relationship with someone ten years older than me I have learned a lot about them and life in general.

Conversations with older men are so intriguing. They can actually hold a good conversation and can talk about anything. They are not surprised about much said because they heard it all before.

Do Something Nice

It seems it’s always expected for the man to pay for the bill at a restaurant, buy gifts, or pay for almost everything, especially when the man is older. People assume the older man is more financially stable, in some cases that could be true. Yet, regardless of the man’s financial status do something nice for him.

The next time you both go out on a date to a fancy restaurant pick up the tab. You could also plan the next date and make it a surprise. Or even better cook for him, men loves when a woman can cook. Ask him what’s his favorite foods and plan a romantic evening at home.

Buy him a gift or two.

Of course, he will never ask you to do anything for him, but doing something nice shows you care. It also shows that in a relationship you can give and not always take.

Compliment Him

Older men might not say it but every once and a while they think about “if they still got it.” This means they wonder if they are still attractive. Since they have gotten older a lot has changed.

They no longer look at how they did when they were twenty-something.

When people get older a lot of changes physically, mentally, and emotionally. It’s always nice to reassure them they are absolutely wonderful, handsome, strong, brave, courageous, vibrant, and the list goes on. A compliment here and there is the ultimate ego booster.


When you decide to date an older man be mentally prepared for whatever he brings to the table. This could mean children, an ex-wife, and numerous responsibilities.

He is older so he comes with a lot of life experiences but the good thing is you can learn a lot from him.

He is a person you can really talk to and trust that he will be reliable when needed.

He understands life a lot better than those you may have dated in the past that were your age or younger.

He is assertive.

He gets down to business.

You will never have to guess what he is thinking because he is the type to get straight to the point. You can always talk to him about anything. When dating him do not think he doesn’t like to have fun because he is older, older men love to have fun. So, entertain him some time. Put on something sexy and rock his world. Give him space when needed. After a while, he will miss you and contact you. Listen to him. Don’t be a nag. Do something nice every blue moon and always compliment him. If you want to find older men to date check out our dating sites page for recommended dating websites.

Dating Older Men What are the Pros and Cons





Recent Posts