Dating An Older Man – The Ultimate List Of Dos and Don’ts

dating an older man

Salt and pepper hair. A face hardened by experience. A certain sense of calmness and stability. There is just much that makes the idea of dating an older man irresistible. Gee, I’m feeling a little weak in the knees even as I write this. Probably because images of George Clooney and Hugh Grant are swarming my mind.

Well, it is surely an exciting proposition. However, like every other relationship, this too comes with its share of problems and pitfalls. That’s why fully understanding the pros and cons of dating an older man is crucial to ensure you’re making the right decision.

Once you’re sure that you’re in it for all the right reasons and decide to take the leap, you’ll have to learn to navigate the relationship maze from a fresh perspective. Having a certain set of rules to guide you can make the journey easier for both partners.

Dating An Older Man – The Rulebook Of Dos and Don’ts

While dating an older man is no longer a big deal, age-gap relationships do come with their unique set of challenges. For instance, your points of reference for things in life or pop culture influence can be markedly different. This can make finding common ground to connect over a lot harder.

This is not to say that dating a man 15 years older or 20 years older can never work out. Or something you should steer clear of at all costs. However, knowing what you’re signing up for helps set and manage relationship expectations more realistically. With the right tips for dating an older man to help you through this journey, you can surely make it a fun and fulfilling ride.

infographic on dating older men

To help you understand what dating an older man takes, we’re here with a rule book of dos and don’ts:

Related Reading: 15 Reasons Young Men Fall For Older Women

1. Do: Discuss what dating means to you both

When starting things up with someone considerably older, there must be absolute clarity about what you both want from the relationship. Let’s say, you’re dating an older man in your 20s. Are you in it just for the experience? Or are you open to the prospect of it turning into something more serious and long-term? Is your potential partner interested in a long-term relationship at that stage of his life?

An honest discussion right at the onset of the relationship can save you from heartbreak or a nasty breakup later. Where do you see this going? – This is definitely one of the questions to ask an older man you are dating. Yes, I get that most couples don’t want to touch that question with a 10-foot pole for as long as they can avoid it, in your case, putting it off may not be in your best interest as a couple.

2. Don’t: Push for what he doesn’t want

What if at some point you become emotionally invested in the relationship even though you agreed to keep things casual? Don’t push him to get into something he doesn’t want or isn’t ready for. Be honest with him about your changing feelings. Leave the rest to him.

You have to be mindful of dating older men psychology before you set your hopes and expectations in stone. Understand that the baggage of his past and clarity about his mortality can be big factors governing his relationship choices.

3. Do: Leverage the benefits of dating an older man and learn from him

An older man brings a lot of experience to the table and that counts as one of the biggest benefits of dating an older man. So, keep an open mind and be prepared to learn from him. He may end up pulling the ‘at your age’ card more often than you like. It can become an irritant, if not taken in the right spirit.

As with anyone with more years and experience behind them, your older partner is likely to be right about most things. So, rather than doing things just to defy him, try to learn from his experiences.

4. Don’t: Lose your individuality

While it’s great to have a partner who can offer you guidance and sage advice at every step of the way, you mustn’t allow him to take over your life. That’s why it’s critical to not lose your individuality when dating an older man.

If you feel strongly about something, speak your mind, put your foot down, stand up for yourself. Even if only to go ahead and make the mistakes he warned you against. He wouldn’t be the wise man he is without making mistakes, stumbling, falling, and then learning to get up and get on with life.

There is no reason why you should miss out on such important learning experiences.

Related Reading: I’m a young mature woman in love with an older man who’s a child at heart

5. Do: Relish your youth

Just because you’re dating an older man in your 20s or 30s doesn’t mean that you have to feel guilty about having youth on your side. There is nothing wrong in secretly savoring the fact that while your man may have his charming looks and wisdom, you have the gift of youth on your side.

The difference in your age doesn’t have to become one of the cons of dating an older man, if you don’t let it. One way of ensuring that is by staying true to who you are at this stage of life without feeling guilty or apologetic about it.

6. Don’t: Rub his old age in

Reveling in the glory of your youth shouldn’t be done at the cost of your partner’s advancing years. For instance, pointing out new grey’s in his hair or commenting on wrinkles on his hand while gently stroking it is a no-go territory.

One of the most crucial tips for dating an older man is to never use his age against him. Even if done in jest, it can be hurtful and damaging to your relationship.

7. Do: Find time for age-appropriate activities

 dating a man 15 years older
You don’t have to put your life on hold

As people in different age brackets – possibly even from different generations – your ideas of fun and relaxation can be opposite to each other’s. He may want to spend a Saturday evening at home, reading and sipping on his scotch. You may want to go clubbing.

Just because you’re dating an older man, doesn’t mean you have to put your life on hold. Get in touch with your friends, make plans, and have fun. It’s healthy to pursue personal interests in relationships. Even more so in the case of age-gap relationships.

Among the many perks of dating an older man is that he’ll always be supportive of your need to be your own person. All you have to do is voice it.

8. Don’t: Pester him to accompany you

Yes, doing things together is an important part of relationship dynamics. However, that doesn’t mean you get to pester him to do things that you find interesting. A pub crawl till 4 am may not only not resonate with him but also will be physically draining.

Instead, find common interests you can pursue to connect on a deeper level. For instance, if you both enjoy reading, a trip to the local library or bookstore, followed by a hearty brunch or coffee date could be a great way to spend a Sunday morning. Fishing, wine-tasting, a romantic outing to the beach, a movie night at home – there are so many activities that you can enjoy as a couple.

Related Reading: 12 Facts Of Older Woman Younger Man Relationships

9. Do: Brace for opinions from family and friends

When you start dating an older man, the possibility of your friends and family reacting less than favorably to the development is very real. From prodding questions about what attracts a younger woman to an older man to advising you against pursuing the relationship, there can be a range of less than positive reactions when you break the news to them.

Having to stand up to societal constructs and others’ ideas of what romantic partners should look like can unarguably feel like one of the disadvantages of dating an older man. Don’t let it get to you though. Be prepared.

10. Don’t: Let it change your mind

If you’re convinced about your feelings for this man, don’t let their opinions influence your decision. Just because your friends or parents don’t approve doesn’t mean you don’t date an older man you have a connection with.

You can try to make them see why you’ve chosen to be with him. Or just give it time and wait for them to come around. As long as you can see the benefits of dating an older man you’re with and being with him makes you happy, that’s all that should matter.

11. Do: Be in tune with your feelings

falling in love with older man
Have clarity about what the future holds for you

As your relationship progresses, you must be in touch with your feelings. Are you falling in love with an older man? Do you feel a deep emotional connection with him? It’s important to be able to answer these questions with clarity to decide what the future holds for you.

Once you do find an answer to these questions, it’s a good idea to check in on how he feels to make sure you’re on the same page. Use the right questions to ask an older man you are dating to get the answers you’re looking for without making him feel pressured to commit to something he may not be ready for.

At the same time, don’t let him pressure you into saying yes to a next step in the relationship if doesn’t feel like you’re ready to take it.

12. Don’t: Assume how he is feeling

Just because he is older and has been through the rigmarole of relationships doesn’t mean he is with you just for the thrill. Even if you both started things casually, it is possible that he too may develop serious feelings for you along the way. Steer clear of assumptions on how he feels about you. If there is ambiguity on the matter, have a frank and honest discussion with him.

Not letting communication barriers in your relationship bog you down is among the most valuable tips for dating an older man. Keep those channels open so that you can have honest and frank conversations about the things that matter.

13. Do: Accept his baggage to understand dating older men psychology

If you’re dating a man 15 years older, perhaps more, there is bound to be some baggage in his life. An estranged spouse. A deceased spouse. Children. Maybe even grandchildren. When you sign up for such a relationship, you have to be accepting of these extensions that are a part of his life.

Doing so will give you a better insight into dating older men psychology and help you understand your partner’s actions better, as you can see where he is coming from on certain issues.

14. Don’t: Let his baggage overwhelm you

If you’re falling in love with an older man, don’t let his life’s baggage overwhelm or deter you from taking things forward. Yes, it can be intimidating to think that you may become a step-parent to his children, who may not be much older than you. Or how his family may react to the relationship.

But, as long as it works for the two of you, trust the other pieces to fall in place with time and a little effort. Know that his family, his past relationships aren’t yours to get involved in until you’re both ready for it. This way you can make one of the biggest perceived cons of dating an older man less intimidating.

15. Do: Show affection

If you’re dating a man who is your senior not by a few years but a couple of decades, romancing him may not come to you organically. Not at first anyway. But don’t let the dad syndrome get in the way of your relationship.

Display your affection through gestures, words, and touch as often as possible. Even if it feels a tad awkward at first, you will find your comfort zone with him eventually. Just ease into it and don’t let any build-up pressure get to you.

Related Reading: 20 Rules Of Dating A Single Dad

16. Don’t: Try to make him jealous

There is a good chance that there may be other guys making passes at you, expressing their interest, or trying to win you over. Using them to make your man jealous is a terrible idea. No matter what your reasons, this approach is sure to backfire. And your relationship may crash and burn, as a result.

One of the biggest advantages of dating an older man is that he is more likely to be secure about you and the relationship. Savor that instead of trying to challenge his sense of security.

17. Do: Have fun

dating older man in your 20s
Keep the relationship fresh

If he brings maturity and stability to the relationship, as the younger partner, you bring freshness and novelty. So, don’t hold yourself back from having fun when you’re with him. Let your hair down, goof around, make him laugh. It will help keep the relationship fresh and brimming with the right vibes.

Help him get in touch with his carefree side, and he might just surprise you with joie de vivre you couldn’t imagine him being capable of.

18. Don’t: Be immature

You have to know the difference between being a whiff of fresh air and acting out like an immature teenager. When you aim for the former, don’t fall into the trap of the latter. Steer clear of temper tantrums, unrealistic demands, or doing irresponsible things that make your partner feels like he is parenting and not romancing you.

He shouldn’t have to watch you get knocked out of your sense drunk, carry you home and care for you just because you want to have some unbridled fun. As a rule of thumb, anything that may make him want to use the words ‘you’re grounded’ qualifies as immature behavior you ought to steer clear of.

Related Reading: 10 Bollywood Age Gap Movies That Show Love Transcends All Bounds

19. Do: Initiate intimacy

It is no secret that the libido takes a hit with age. But that doesn’t mean that action in the bedroom has to remain dormant unless your man is feeling up for it. That may require you to initiate intimacy to get him in the mood. Don’t hold yourself back.

Take charge in bed, experiment a little, be prepared to lead at times and follow at others, and brace yourself to have your mind blown when he shows you how well he knows his way around a woman’s body.

20. Don’t: Disregard his limitations

In case you’re dating a man 15 years older or more, you have to be mindful of the fact that his reluctance to get things going between the sheets may be more than just about reduced libido. Achy joints, back pain, prostate issues, poor digestion – these are all common in older men.

These can become a deterrent to intimacy. Don’t disregard any valid health concerns he may have just because your hormones are raging and raring to go. Without a doubt, these limitations can feel like disadvantages of dating an older man. But then, which relationship is free from its share of pros and cons.

As long as you’re both emotionally invested, you’ll find a way to work around it.

21. Do: Treat him as you would any partner

don't date an older man
Shed aside the awe and embrace him for who he is

Just because you’re separated by your years doesn’t mean you have to treat him any differently than you would another romantic partner. This includes shedding the tendency of shying away from showing your romantic side as well as treating him with a sense of reverence. Shed aside the awe, and embrace him for who he is – your partner.

With the right approach and mindset, dating an older man can be a delightful and enriching experience. One that may change your perspective on relationships forever. If you have your heart set on one, don’t hold yourself back. When you do decide to give in, these tips for dating an older man will hold you in good stead.


1. How do you tell if an older man loves you?

When an older man loves you, he will go out of his comfort zone to make you feel special. Things between you both will progress to a deeper level. He won’t hold back from sharing his feelings with you once he is sure of them.

2. Is dating an older man better?

Yes, dating an older man can be better because of all the experience, stability, and sense of security he brings to the relationship. With him, there will be no mind games or hot-and-cold vibes.

3. What does an older man want in a relationship?

He may want a casual fling or a serious committed relationship. There is no way to define relationship expectations based on age alone. It varies from person to person.

4. How much of an age difference is OK when dating?

It is not common to be dating a man 15 years older or 20 or even more. As per the old dating age rule, the maximum acceptable age difference is calculated with a simple formula – half his age + 7 years. So, if you’re 25, your partner should be in the 38 to 40 years age bracket.

I Am Attracted To A Younger Man Who Is The Opposite Of My Husband

10 Things That Attract A Woman To A Man Instantly

I had a Crush On An Older Woman and It Changed Me


This website uses cookies to ensure you get the best experience on our website.