Dating An Older Man: 21 Dos and Don’ts To Make It Work

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Salt-and-pepper hair, a face hardened by experience, and a certain sense of calmness and stability – there’s a lot that makes the idea of dating an older man irresistible. Well, not every older man may give you goosebumps like George Clooney or Hugh Grant, but dating a man 15 years older, or 20, is surely an exciting proposition, as they are more mature and less likely to play games. This probably also answers the question, “Why are young women into older men?”

But while women dating older men is quite normal, like every other relationship, this too comes with its share of problems and pitfalls. So, understanding the pros and cons of dating an older man is crucial to ensure you’re making the right decision.

In this article, we will delve deeper into the possibilities, advantages, pitfalls, and expectations that come along with a relationship with older man, backed by expert insights from 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. We will also give you some tips on dating an older guy. So, let’s begin…

What To Expect When Dating An Older Man — Advice From Expert

So, you are attracted to someone who carries all the markers of his age — the salt and pepper hair, the lines hardening his face just a little — with grace. To top it all off, he is knowledgeable and kind and makes your heart skip a beat. You want to take the leap your heart’s been egging you on to but perhaps you’re not quite sure how to date an older man. Or maybe, you’re already dating a man 20 years older but don’t what to expect from this relationship.

We’re here to help. Women dating older men is nothing new, but being romantically involved with an aged man has both pros and cons. You should know that it may not always be a smooth sail even though you feel this intense physical and emotional attraction toward him. This is primarily because such unorthodox partnerships are often influenced by many external factors. Now that you are trying to decode the ‘dating older men psychology’ and wondering what to expect when dating an older man, let’s delve deeper into this.

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Our expert Jayant lists some positive aspects of such older male younger female relationships that can answer your question, “Why are so many young women into older men?”:

  • Older men are a ‘good catch’: The best part about dating an older guy is that by the time you get to know this person, he has already become the finest version of himself. His personality has been processed over time. Jayant says, “He has had his own journey and his ups and downs. He is probably both mentally and financially stable.”
  • There’s better clarity: An older man is most likely to be clear about his expectations from the relationship. He is likely to have dated other women in the and there’s less chance of silly relationship mind-games
  • They are likely to be more mature: Jayant believes, “A relationship with older man is likely to be mature, as such men are better in terms of maintaining the relationship.” He won’t be afraid to apologize or take ownership of his actions. He will have a softer male ego and less relationship insecurity or fear of commitment

Speaking about the pros and cons of dating an older man, Jayant points out a few red flags when dating an older man in your 40s, 30s, or even 20s:

  • 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
  • Lack of flexibility: His opinions and attitude are likely to be rigid and he may not be open to change
  • Your interests may clash with theirs: You might start liking people of your age group better by the time you grow up to be of a certain age

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 in your 20s or 30s is no longer a big deal, age-gap relationships do come with their unique set of challenges. For instance, your cultural references or social life 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 Clooney tied the knot in 2014 and have been going strong and raising two beautiful children together. While these celebrities have the social status and support to pursue such unconventional partnerships, it may not be the same for an average couple.

Related Reading: Men Over 50 – 11 Lesser Known Things Women Should Know

This is not to say that dating a man 20 years older or more can never work out. Take the instance of my neighbor, Sylvie, who was 25 when she fell for her professor, who was well in his 40s. They took their relationship forward after Sylvie left the college and remained in touch even when she relocated to another city for work. They eventually got engaged last summer.

However, knowing what you’re signing up for helps you manage relationship expectations more realistically. Now that we know the answer to, “Why are so many young women into older men?”, we’ll look at how to go about it. To help you understand how to date an older man, we’ll present to you certain rules for dating an older man. You may also call these pieces of advice for 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 a mature older man in your 20s. Ask yourself questions such as:

  • Are you in it just for the experience?
  • 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?” is definitely one of the questions to ask an older man you are dating.

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

2. Don’t push for what he doesn’t want

One of the rules for dating an older man is to not force him to do what he doesn’t want to. One such instance is when a woman gets emotionally invested in the relationship that was initially meant to be casual and then starts to push the man into committing quickly.

If you ask us for tips for dating an older man in your 20s or 30s, we would suggest not to push him to get into something he doesn’t want or is not ready for. Here’s what you should do instead:

  • Be honest with him about your feelings and leave the rest to him
  • Understand that the emotional baggage from his past relationships can control his relationship choices
  • Be prepared to talk to him about practicalities, such as mortality

3. Do learn from him

One of my friends, Cathy, who has had some personal experience with an older man, said, “I’ve been sleeping with a man 20 years older than me and the best part is, I feel he is so knowledgeable, not just about sex but about life, in general.” A lot of women like older guys because an older man brings a lot of life experience to the table. In fact, being in a mature relationship is one of the biggest benefits of dating an older man. So, keep an open mind and be prepared to learn from him. Remember:

  • He may end up pulling the ‘at your age’ card more often than you like. Take it positively
  • As with anyone with more years and experience behind them, your older partner is likely to be right about many things
  • Instead of defying him, it may be wiser to learn from his experiences

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

Dina, one of our readers from Chicago, tells us, “A relationship with older man is tricky! When I started dating Michael, I would often be worried about insignificant matters, like how should I dress when dating a mature older man or what if he tries to impose his views on my life?” His emotional maturity became a major strength 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

A coworker of mine, Alice, a young woman in her early 30s, once told me, “I dated a man for 8 years. He was almost a decade older than me and started controlling every aspect of my life. We parted ways after our relationship turned sour due to arguments.”

What attracts a younger woman to an older man most is his wisdom. While it’s great to have a partner who can offer you guidance and sage advice at every step of the way, on the flip side, you can become too dependent on him. So, you mustn’t allow him to take over your life, as it’s critical to not lose your individuality when dating an older guy. Here’s what you should do instead:

  • 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, try doing things on your own at times
  • Be financially independent and learn to take care of your own needs

Jayant says, “Any relationship should be an addition to the happiness that already exists in your life. 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 be mutually fulfilling, with both of you moving steadily on your own paths while being intertwined for a while.”

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. One of the advantages of dating an older man is that you’ll always be ‘young’ beside him. There is nothing wrong with secretly savoring the gift of youth. So, don’t skip that hike to the Grand Canyon that’s on your wish list simply because your partner doesn’t want to join you.

Related Reading: 12 Best Dating Sites For Seniors Over 60

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. So, don’t make him conscious of his age. For instance:

  • Stop pointing out his greying hair
  • Don’t comment on his wrinkles
  • Don’t ridicule him for his lack of pace during your early morning jogs
  • If he’s retired, don’t joke about him having too much free time

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

Age-gap relationships may have partners belonging to different generations. So, it’s quite possible for a partner tp find it difficult to participate in activities that draw the other. As a woman dating an older partner, your idea of fun may not match with his. 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.

relationship with older man
Age-appropriate activities can prevent your old man-young woman relationship from turning boring

So, here’s what you can do instead:

  • Embrace the differences. Just because you’re dating a mature 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, try out new things, and have fun. It’s healthy to pursue personal interests in relationships
  • Be clear about your likes and dislikes. Among the many perks of dating an older man is that he’s likely to be supportive of your need to be your own person

Related Reading: 21 Things To Know When Dating A Man With Kids

8. Don’t pester him to accompany you everywhere

Yes, doing things together is an important part of relationship dynamics, even if it’s an older man and younger woman relationship. 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 be your idea of fun but may not resonate with him. Now, you may be wondering how to date an older man without accidentally coming across as an insensitive partner. Here’s what you can do:

  • 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.
  • Go for couple-friendly activities nearby that you’re both likely to enjoy. 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

9. Do brace yourself for opinions from family and friends

When you start dating a mature older man, the possibility of your friends and family reacting less than favorably to the development is very real. The moment you declare, “I like an older guy”, There can be a range of negative reactions — from questions about what attracts a younger woman to an older man to suggestions against pursuing the relationship.

Don’t let it get to you though. Take it as one of the 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 those around us tend to think in black and white. They don’t understand how this world is gray. They will keep coming back to the age gap.”

Related Reading: 12 Facts Of Older Woman Younger Man Relationships

10. Don’t let others change your mind

If you’re convinced about your feelings for this man, don’t let others’ opinions on the negative consequences of dating an older man influence your decision. Just because your friends or parents don’t approve doesn’t mean you shouldn’t date an older man you have a connection with. Be proud to declare, “I like an older guy.”

Here’s what you should do instead:

  • Don’t let your loved ones’ judgment change your tracks
  • Set boundaries for your family and friends and let them know what is acceptable
  • Let them know that dating an older guy was your personal choice as an adult. You can try to make them see why you’ve chosen to be with him
  • Give it time and wait for them to come around

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, the 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 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.

Related Reading: 11 Expert Tips To Have A Successful Second Marriage

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.

So, speak up if you’re falling in love with an older man. If there is ambiguity, have an 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 there’s room for open communication about the things that matter.

13. Do accept his baggage

Even if you’re dating an older man in your 40s or 50s, there is bound to be some baggage in his life. An ex-wife, memories of a dead spouse, children, grandchildren — the list can be endless. 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 and help you understand your partner’s actions better, as you’ll see where he is coming from on certain issues.

Related Reading: 21 Tips For Dating A Widower

14. Don’t let his past overwhelm you

Don’t date an older man, if you let his past overwhelm you 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.

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 just by a few years but a couple of decades, romancing him may not come to you organically. You may wonder how to date older men and show them you care. Well, don’t let the ‘dad syndrome’ get in the way of your relationship. Here’s what you can do instead:

  • Display your affection through gestures, words, and touch, as often as possible
  • Slide into a little PDA if he is okay with it
  • Even if it feels a tad awkward at first, try and find your comfort zone with him

Related Reading: 20 Rules Of Dating A Single Dad

16. Don’t try to make him jealous

Don’t date an older man if you intend to make him jealous with your younger conquests. 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. 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

Women like older guys because they bring emotional maturity and stability to the relationship, but as the younger partner, you should not hesitate to 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, and 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 his joie de vivre.

Stories on Older Man Younger Woman

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. So, avoid:

  • Temper tantrums
  • Unrealistic expectations
  • Irresponsible activities that make him feel like he is parenting and not romancing you

While one of the benefits of dating an older man is that he will always care about 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. In fact, this is one of the disadvantages of dating an older man. 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. Here are some things you can try:

  • Take charge in bed and initiate sex by kissing or touching him
  • Experiment a little with different positions or even sex games for couples, like role-playing
  • Be prepared to lead at times and follow at others
  • Don’t be surprised 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. He could be a victim of all or any of the following:

  • Achy joints
  • Back pain
  • Prostate issues
  • Poor digestion
  • Mental blocks

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.

Related Reading: 23 Things Mature Women Want In Relationships

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, and equipped with the tips on dating an older guy we have provided in this article, you may find being with an older man a delightful and enriching experience — one that may change your perspective on older male younger female 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 guy 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 on 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 at times, because of all the experience, stability, and sense of security he brings to the relationship. With him, you may not have 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 okay when dating?

It is not uncommon to be dating a man 15 years older, or 20, or even more. 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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