Tips for Dating a Man Twenty Years Older - Cool Dating Advice

Tips for Dating a Man Twenty Years Older

Everyone always says that when it comes to relationships, age is just a number. This is true, but it can sometimes have an effect on dating and relationships if you don’t go about it in a good way.

You shouldn’t let age stop you, but at the same time, you should focus on the aspects of the age gap that have big roles in your relationship. Don’t worry about being judged for going after an older man, it only matters if you are happy. Here are some tips about dating an older man.

Don’t focus on age

If you spend your whole relationship being concerned about the age gap, it will have negative effects on your relationship. If you think about it too much, you may realize he’s closer in age to some of your family members than you, like say your father.

It may seem weird, but you two found each other for a reason, and if you weren’t okay with the age, you wouldn’t be in this situation.  If he notices that you make comments about it all the time, and can’t stop focusing on it, he may not think that you want to stick with him. It may make him feel insecure, and you don’t want him to feel like that.

You’re in different stages of life


You both are in totally different stages of life… and that’s okay! Embrace that and learn from each other. Basically, just realize he may not want to do everything that you want to do.  Don’t expect him to go out and party with you. He has already had plenty of that and is just in a different stage of life.

If you want someone to party with, this may not be your fit. At the same time, he also needs to understand the same thing about you. You guys can both have fun and live your own lives while knowing that you will always have each other and everything that goes along with that.

Stable life

When dating an older man, it is nice to know that you will always have a stable life. He will have a stable job and house and you will never have to worry as much.

It is not like dating someone who is just out of college and has no stability.

This isn’t like being in high school or college and dating a boy who has no idea what he is doing with his life. You are dating someone who has already built a life. This is a great aspect of dating an older man and gives you the opportunity to live your life to the fullest.

Make sure to always tell him how appreciative you are for this.


Focus on his maturity.

Also, focus on being mature as well.

He doesn’t want to date someone who is immature, he wants a serious relationship, or he wouldn’t be after you. This is probably one of the main reasons that you were attracted or him. No more immaturity with an ignorant boy, you wanted a man.

This is not the kind of man who is going to break up with you over text. This is the kind of man who will hold doors for you, buy you flowers, make you a homemade dinner and treat you will.

Older men know how to show your appreciation because they have already been involved with enough girls to know the dos and don’ts. They have probably been hurt before and they know that you deserve to be respected and treated right.


Be thankful for this and make sure he knows that you are thankful for this. It is important to focus on these things If you are ever feeling down about anything that is going on in the relationship.


Not only will you man be confident about himself, but he will also give you so much confidence and self- esteem. You need to realize that older men are looking for confident women because they don’t want to play games.

Don’t play with him and don’t play with his heart.

He has had enough games in his life, and he doesn’t need anymore. Treat him right and he will make you the happiest girl in the world.

Also, not only will you man be confident about himself, he will give you so much confidence and self- esteem. He will worship the ground you walk on, so give it right back to him. Hype him up and make him feel young again. 


Realize that he will know more about life than you. This does not mean that he is smarter than you, it just means that he has lived through more than. Take his advice and don’t be ashamed of your age, youth, and wisdom. Listen to what he has to say and ask him about his life. Make him feel good about his knowledge.

Don’t be jealous

An older man is not going to get jealous of young guys around you because he is confident with what he has, and if you’re willing to hurt him, he’s willing to let you go.

He does not want someone who is immature and playing games. If he is not going to get jealous, you need to do him a favor and lose the jealousy as well. Don’t be jealous of other lady friends in his life, or women at work. You have to give him the benefit of the doubt and treat him the way that you wanted to be treated.

Remember that he has probably dealt with a few emotional women in his life.

Family and friends

Don’t be surprised if it takes a little bit for your families to warm up to the idea of you two being together. Don’t let this affect your relationship, because eventually once your family realizes that you two are in this for real, they will accept it.

On this note also don’t focus on what everyone else thinks in general. Your friends may not agree with it at first, and others may look at you and make comments in public.

You have to take this with a grain of salt and get over it.

If you are happy nothing else matters, and you should never let other people’s opinions affect your happiness. Be proud of your man. Introduce him to your friends and family and be proud to show him off. If they see how happy and proud you are, they will accept it.

He has had a whole life before you

It is important to remember that your man has lived an entire life before you. Get to know about his past, and plan for your future. You need to know about his past life in order to understand who he is. Your past makes you who you are. It is important to get to know the people in his life too.

Don’t be jealous that you don’t know any of these people or anything about his life, you are learning and you two are about to make a new life together.

You won’t have the same friends… and that’s okay!

When dating an older guy, you may not always have common friends. You can make friends with his friends, as he can with yours, but normally you will also both have groups of friends around your specific age group.

You need to realize that this is okay!

Neither of you should have to give up friends. Keep your friend groups, have fun, live your life, and appreciate your man. Don’t try to force him to be friends with a bunch of young girls. Bring him around, show him off, but still go out and have fun with your friends.

You both deserve to have happy lives outside of the relationship. As long as you don’t get hung up on these things and focus on them too much, your relationship will be just fine. Like I said earlier, if you focus too much on having different friends, it will have a negative effect on your relationship. Just focus on being happy and making your man happy too.


Overall, as long as you are okay with dating an older man and all the things that come with it, you will successfully have a healthy, happy relationship. In the end, it is all up to you, how you feel, and what makes you happy. As long as you don’t let other opinions dictate your relationship, everything will be fine.

Forget jealousy and focus on appreciation and maturity.

Between the two of you, you will have so much knowledge about different areas, and such a mature relationship, that you are bound for success. You guys can live a happy, stable life and prove to others that age really is just a number. You can prove to others that it doesn’t matter what age you are when you have found someone tha27t you really click with. Love is a beautiful thing and should be defined by numbers.

If you are dating someone with kids check out our article how to date someone with kids. Great insight into what to do when kids are involved.



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