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20 tips for dating an older man you need to know about!

Dating older men can be a totally different and sometimes even scary experience. But don't worry; we're here to help you make this one of the best times of your life!

Author picture of Janet Smith
Dating Expert Janet Smith October 11, 2022 • 9 minutes read
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So, you’re dating this older guy, and you’re wondering what the heck you got yourself into, huh? Well, don’t worry – we’re here to help.

Dating an older man is actually way easier than it sounds. So, buckle up, and let’s get started.

Here are 20 tips for dating an older man that will help keep things fun and easygoing:

1. Communicate openly

1. Communicate openly

It’s important to communicate with your older partner about what you’re looking for in the relationship. If you’re not on the same page, it can be easy to get frustrated or feel like you’re being taken advantage of.

You should also feel comfortable communicating your needs and boundaries. An older man should be respectful of your wishes and not try to push you into anything you’re not ready for.

Are you unsure of why he’s into you? Here are the 10 most common reasons why older men date younger women!

2. Don’t be afraid to be assertive

If you want something, don’t be afraid to go after it. Older men respect women who are assertive and confident. He’ll be more likely to respond positively to your needs if you’re direct about them.

Just because he’s older doesn’t mean he knows everything. If you want something, don’t be afraid to ask for it. He’ll respect you more for being direct, and he’ll be more likely to give you what you want.

It’s important that you see yourself as an equal. Just because you’re younger than him doesn’t mean you’re lesser than him in any way.

3. Be confident

One of the most attractive things about dating an older man is your confidence. He’s attracted to you because you’re young and vibrant, and full of life. So, don’t be afraid to show it!

Be confident in yourself and in your relationship. Older men can be attracted to women who are confident and secure in themselves despite dating a man that isn’t their age.

4. Be honest about your intentions

4. Be honest about your intentions

If you’re only dating an older man because you think it’ll make you more mature or because you want to experience something different, you’re not being honest with yourself or with him. Be upfront about your intentions from the beginning.

It’s okay to want to date an older man because you’re attracted to him or because you’re looking for a different type of relationship than you’re used to. But don’t lead him on if you’re not interested in something long-term.

5. Keep things fun and easygoing

One of the best parts about dating older men is that they tend to be more laid back than guys your own age. They’re usually not into playing games or drama, so things tend to be more relaxed and easygoing.

This doesn’t mean you should take advantage of his laid-back attitude or that you shouldn’t communicate with him about your needs. It just means that you can usually expect things to be a little less complicated than they would be with a younger man.

Do you want to know more truths and tips about dating older men? These 15 will enlighten you!

6. Enjoy your conversations

Older men usually have a lot of interesting stories and experiences to share. They’ve had more time to live life, and they’re usually more than happy to talk about it.

But that doesn’t mean you should just listen and not contribute to the conversation. Older men also love women who are intelligent and can hold their own in a discussion. So, don’t be afraid to share your own stories and experiences.

So, enjoy your conversations! Ask questions and be interested in what he has to say. You might learn something new or get some new perspectives on life.

7. Don’t move too quickly

7. Don't move too quickly

Don’t assume that just because he’s older, he’s looking for a serious relationship right away. Some older men just want to date casually or might be getting over a previous relationship.

So, take things slow, and don’t assume that he’s looking for something long-term just because he’s a little older than you. You need to talk about that.

8. Show him new things

He may have seen a lot in his life, but not everything. Showing him new things is a great way to keep things fresh in your relationship.

It doesn’t have to be anything big or expensive. Just something that you think he might enjoy or find interesting. It’ll show him that you’re interested in him and that you care about his interests.

To show him something new, you often don’t even need to leave the house. Suppose he’s only enjoying old movies; show him something from the last five years!

You may find that he loves it, or you might have an interesting discussion about the differences between then and now.

How about showing him some current-generation humor? These 37 “dating me is like” jokes are a banger!

Maybe you can come up with your own as well!

9. Don’t try to change

This is probably the most important tip on this list. You should never try to be someone you’re not just to please him or to fit into his life. He’s attracted to you for who you are, so don’t try to change that.

Of course, there’s nothing wrong with growing and changing as a person. But that should come from within yourself, not from someone else’s expectations.

If you’re trying to be someone you’re not, it’ll eventually catch up to you.

10. Let him take the lead

10. Let him take the lead

He’s still the man, so let him take the lead sometimes. This doesn’t mean that you should be a doormat or that you should let him make all the decisions. It just means that you shouldn’t be afraid to let him take charge every once in a while.

This is especially important if he’s a lot older than you. He may have some conservative views, but that doesn’t mean you should change your own views to match his.

It’s okay to disagree and to have different opinions. That’s what makes relationships interesting!

11. Be supportive

Just because he’s older doesn’t mean he doesn’t need a shoulder to lean on. Everyone goes through tough times, and he’ll appreciate your support when he’s going through a tough time.

Of course, you shouldn’t be his only source of support. He should have friends and family that he can rely on too. But it’s still important to be there for him when he needs you.

12. Laugh at mistakes

We all make mistakes, and no one is perfect. So, don’t be too hard on him or yourself if anyone of you makes a mistake. Just laugh it off and move on.

Making mistakes is part of life, and it’s important to be able to laugh at them. It’ll help you both to relax and not take things too seriously.

13. Accept his flaws

Nobody’s perfect, and that includes older men as well. So, don’t expect him to be perfect. He’s going to have his own set of flaws and quirks, just like everyone else.

And that’s okay! Nobody’s perfect, and you shouldn’t expect him to be. Just accept him for who he is, flaws and all.

14. Accept his baggage

Everybody gathers a little bit of baggage as they go through life. And that includes older men as well. So, don’t be surprised if he has some baggage of his own.

He may have an ex-wife, children, or even debts. And again, that’s okay! We all have baggage, and it’s nothing to be ashamed of. Just accept it and move on.

15. Don’t be too clingy or needy

15. Don't be too clingy or needy

One of the worst things you can do in a relationship is to be too clingy or needy. This will only push him away and make him feel suffocated.

Of course, it’s normal to want some attention and affection from your partner. But don’t go overboard. Give him some space, and don’t be afraid to do your own thing sometimes.

If you’re scared because you don’t know if he has strong feelings for you or not, you should check out these 22 telltale signs!

16. Don’t play games

Older men have usually been through a lot of relationships, and they know when someone is playing games. So, don’t try to play games with him. Just be honest and upfront about your feelings.

He’ll appreciate your honesty, and it’ll make your relationship stronger in the long run.

17. Discuss the future

After being in a relationship for a while, it’s normal to start thinking about the future. So, don’t be afraid to have a discussion about where you see things going.

Of course, there’s no need to make any long-term plans just yet. But, it’s still important to talk about your hopes and dreams for the future. This will help you to see if you’re on the same page.

18. Be patient

Things may move a little slower than you’re used to, so it’s important to be patient. This is especially true if he’s a lot older than you. He may not be as active or energetic as you are, and that’s okay.

Just take things at his pace, and don’t try to push him to do things that he’s not comfortable with.

19. Have realistic expectations

19. Have realistic expectations

One of the worst things you can do is to have unrealistic expectations. So, don’t expect him to be perfect or to always agree with you. Just accept him for who he is, and don’t try to change him.

And don’t expect the relationship to always be exciting and perfect. There will be ups and downs, just like in any other relationship.

20. Enjoy your time together

At the end of the day, it’s important to just enjoy your time together. Don’t stress about the little things and just focus on enjoying each other’s company.

After all, that’s what relationships are all about! So, just relax and enjoy your time together.

There you have it. 20 tips for dating an older man. Just remember to take things at your own pace, and don’t be afraid to be honest with him. If you do that, then you’ll be sure to have a happy and healthy relationship. Thanks for reading, and good luck!

New guides for love and dating: Books every woman should read

Navigating the world of dating and relationships as a woman can be tough. There are so many different expectations and standards to uphold, and it can be difficult to know where to turn for advice. If you're looking for some guidance, check out this list of books about relationships and dating for women.

  1. Flirting: How to Flirt for Women Wanting to Date a High-Value Man, Including Seductive Body Language Techniques and a Guide to Get Your Ex Back
  2. Handle with Care: A young woman's guide to identity, self-worth, purpose, and relationship
  3. Dating with Purpose: A Single Woman's Guide to Escaping No Man's Land
  4. Dating for Women: Modern Woman Dating Guide (The Modern Dating Series)
  5. The Awakened Woman's Guide to Everlasting Love
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Author picture of Janet Smith
Dating Expert

Janet Smith

Janet Smith is a freelance writer who writes about psychology, relationships, and dating. She has always been interested in understanding the human brain and how it affects our …

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