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

October 15, 2022 |
dating an older man
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Salt and pepper hair. A face hardened by experience. A certain sense of calmness and stability. There is 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.

If you want to dig a little deeper into the consequences of dating an older man or the possible red flags when dating an older man, you are in the right place at the right time. Having a certain set of rules to guide you can make the journey easier for both partners.

We are here today with a bunch of advice for dating an older man, backed by psychologist Jayant Sundaresan (Masters in Applied Psychology), who specializes in offering counseling for a range of relationship issues such as communication breakdown, expectation management, infidelity, separation, and divorce.

Dating an older man? What to expect – advice from Expert

So you are falling for this amazing human being who’s some 15 to 20 years older than you and you are not quite sure how to date an older man or what to expect from this relationship. Now that you are trying to decode the dating older men psychology, let me tell you, being romantically involved with an aged man has its own set of perks and stability.

At the same time, you should know that it may not always be a smooth sail even though you feel this intense physical and emotional attraction toward him. Mainly because such unorthodox partnerships like yours are often influenced by many external factors.

Jayant says, “First, we have to clarify how much older is ‘older’. Is it a couple of years or are we talking about almost a generational gap? Then certain interesting things might come into play. Let’s say the younger partner is in their mid-20s and the man is in his 40s. If we increase the age by ten years for both, it would still fit this scenario. But their dynamic would be very different. 

“That ten-year gap would create a huge difference for the younger partner. In their 20s, they are still exploring certain things for the first time. So in ten years, they will have the opportunity and experience to understand themselves better. That wild urge for experimentation in dating is more or less done.

“When they meet an older man, an instant comparison with men of their own age group takes place. They will find men of their age lacking in certain areas, which becomes one of the reasons for this attraction. The best part about dating an older man who is a good catch is that by the time you get to know this person, he has already become the finest version of himself which has been processed over time. 

“He had his own journey, his ups and downs. Over time, he might have mellowed down in particular areas. Now he comes across as a much more calm and relaxed person who’s not in a hurry. He is also likely to be very clear about his expectations from this relationship. There won’t be any silly relationship mind games likes the ones that play out with men of your own age.” 

When asked how to date older men, our expert suggests, “An older man won’t be afraid to apologize or take ownership of his actions. With him, you will experience a softer male ego and less relationship insecurity and fear of commitment. Rather, you are the one who needs to be sure about why you are with him. Is this a pattern or a one-time thing? Are you ready for the long run or just want to live in the moment and see where it goes?”

On the flip side, Jayant points out two major downsides of dating an older man in your 40s (could be 20s or 30s too):

  • The past baggage: You have to be ready for him to have a past, particularly in terms of relationships. He may even have children who are probably closer to you in age. If he is a well-maintained handsome man, you may not always see that age difference immediately until you meet his children. It can hit as a stark reality
  • Lack of flexibility: He may be very set in his ways. His opinions and attitude would be based on his personal life experiences, be it negative or positive. The openness we have when we are younger can be missing in him. He is no longer willing to change, unlike younger men who are still on their journey. So, you are either dating a finished product or a work in progress 

Related Reading: 15 Reasons Young Men Fall For Older Women

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.

When George Clooney told Esquire, “At 52, I found the love of my life and I’m really happy. I’ve never been happier in a relationship by any stretch of the imagination”, it sounded like the most romantic thing in the world. Despite having a 17-year age gap, George and Amal tied the knot in 2014 and have been going strong ever since then and are raising two beautiful children together. The relationship trajectory ran quite similar for another celebrity couple, Alec Baldwin and his 26-years-younger wife Hilaria.

While these celebrities have the social status and support to pursue such unconventional partnerships, it may not be the same for an average couple. As a generation who grew up rooting for Monica and Richard in Friends, dating an older guy is certainly not taboo for us. But before you go ahead and romanticize these famous couples, you should take a glance at the real-life struggles of sustaining such a relationship in the long run.

This is not to say that dating a man 15 years older or 20 years older can never work out, or that it’s 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. To help you understand what dating an older man takes, we’re here with a rule book of dos and don’ts:

infographic on dating older men
Dos and don’ts of dating an older man

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. But in your case, putting it off may not be in your best interest as a couple.

Related Reading: Stereotyping Men: Why It’s Time To Think Outside The ‘Man Box’

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? If you ask us for tips for dating an older man, we would suggest not to push him to get into something he doesn’t want or is not 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 emotional 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 many things. So rather than doing things just to defy him, try to learn from his experiences.

Dina, one of our readers from Chicago, tells us, “When I started dating Michael, initially I was worried about insignificant matters like how to dress when dating an older man or what if he tries to impose on my life like a guardian instead of being an equal partner. But his maturity and emotional availability became major strengths in our relationship. No one else could ever pacify my anxiety attacks with so much calm and patience as him.”

4. Don’t: Lose your individuality

One thing that attracts a younger woman to an older man is his wise nature. 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, and 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.

According to Jayant, “Any relationship should be an addition to the happiness that already exists in your life. Then there won’t be an issue of individuality. But if this is what your life starts and finishes with, then your sole existence is defined by the relationship. The whole experience of dating an older guy should look something like this – both of you are moving steadily on your respective life journeys while they are intertwined for some time.”

Related Reading: The 7 Types Of Boundaries You Need To Make Your Relationship Stronger

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 with secretly savoring the fact that while your man may have his charming looks and wisdom, you have the gift of youth as well.

Don’t skip that hike in the Grand Canyon you have on your wish list simply because your partner doesn’t want to come or won’t be able to manage physically. The difference in your age doesn’t have to become one of the cons of dating an older man. 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 greys in his hair or commenting on wrinkles on his hand 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 and that’s one thing you have to be mindful of to get a better grasp on the ‘dating older men’ psychology.

7. Do: Find time for age-appropriate activities

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. Don’t be too quick to mark this difference as one of the red flags when dating an older man.

Embrace the differences. Just because you’re dating an older man, doesn’t mean you have to put your life on hold or that he has to radically change who he is for you. 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.

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

8. Don’t: Pester him to accompany you everywhere

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 a.m. may not only not resonate with him but will be physically draining too. Then how to date an older man without accidentally coming across as an insensitive partner?

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 for these consequences of dating an older man.

Jayant says, “Very rarely would you find someone in your family and friends who will give you valid tips for dating an older man or share their thoughts objectively. They will come with their own agendas, projecting their own fears on you. The majority of the people around us tend to think in right and wrong, black and white. They won’t understand how this world is gray. They will keep coming back to the age gap.

“Your family will speak from the perspective as if they are observed by a judgmental audience. Now that you are going out of the typical standard marriage template, how will your parents explain it to their community and other family members? They may not get the concept of personal choice. When it comes to society, anything that is radically different or out of the box is unacceptable.”

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.

Jayant suggests, “How you filter the external validation and the pieces of advice for dating an older man is an extremely personal decision. You have to ask yourself some basic questions. What do you love about this person as an individual? Do you love the version of yourself that your partner brings out in you? If you are clear in your mind as to why you are in this relationship, opinions of a third person won’t really matter.”

11. Do: Be in tune with your feelings

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 intimacy 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’s not ready for. At the same time, don’t let him pressure you into saying yes to the next step in the relationship if you are not 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 an older man in your 40s with 15 years of age gap, 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 the ‘dating older men’ psychology and help you understand your partner’s actions better, as you’ll 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 you’ll dread thinking about 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 and 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.

Jayant says, “Everybody is at a different level of being evolved and dealing with their burden from the past. It brings us back to the question of how mature you are and whether you have processed your own emotional baggage. You have to spend more time with your partner to understand them and note which parts of them are unalterable. It’s better to stay focused on the good things coming along with the relationship rather than fixating on the negatives.”

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. “How to date older men?” you wonder. Well, 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. Maybe slide into a little PDA if he is okay with it. 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 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

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. Don’t think too much about how to dress when dating an older man or how to sound smart to impress 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 too and he might just surprise you with joie de vivre that you couldn’t imagine him being capable of.

dating older man in your 20s
Keep the relationship fresh

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 feel like he is parenting and not romancing you.

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

Related Reading: 10 Signs Of Emotional Attraction From A Man

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 especially if your man is feeling up for it. He may require you to initiate intimacy to get him in the mood. Don’t hold yourself back from displaying your wild side.

Take charge in bed, experiment a little with different sex games for couples like role-playing, 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 your 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 deterrents 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

Just because you’re separated by your years doesn’t mean you have to treat him any differently than you would another romantic partner. Shed the tendency of shying away from showing your romantic side and don’t treat him with a sense of reverence. Put 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 someone, 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 two 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 uncommon 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-year age bracket.

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