Men Over 50 – 11 Lesser Known Things Women Should Know

Single and Dating | | , Editor-in-Chief
Updated On: November 7, 2023
Lesser Known Things Women Should Know

So, you’re drawn to a man over 50 and wondering what to do about it. Don’t worry, you’re not alone. Men over 50 have a certain enigma and charm to them. Having been through the grind, they appear to be more confident, self-assured and comfortable in their skin. That’s why a lot of women find themselves drawn to men in this age bracket.

However, underneath this calm and comfortable persona may be a host of insecurities, inhibitions, emotional issues and triggers. You know, unless you’re George Clooney. And it’s possible even he occasionally wakes up and wonders if he’s pretty enough. These can make a man in his 50s a complex riddle to solve.

If you’re drawn to someone like that, it helps to get a reality check on the good, bad and ugly about men over 50 to understand what you’re signing up for. We’re here to help on that front with this lowdown on the lesser-known but important facets of men over 50.

Men Over 50 – 11 Lesser Known Things Women Should Know

It’s hardly unusual to come across single men over 50 today. However, not all singles at this stage in life have the same experience and expectations. Individual circumstances have a considerable bearing on men over 50 and their preferences vis-à-vis dating, relationships as well as their world view and attitudes.

For instance, a man who has been single by choice all along will have fewer inhibitions about cultivating romantic relationships than someone who has been through a divorce or lost his life partner. On the flip side, he may be a commitment-phobe or someone with an insecure attachment style, which is why he has remained unattached all along, despite being one of the most handsome men over 50 you’ve ever come across.

What do relationships and romantic partnerships mean to men over 50 living the single life? What are the limitations and advantages of dating in 50s? Here are 11 lesser-known things to be mindful of when considering getting romantically involved with a man in his 50s:

Related Reading: 21 Dos And Don’ts When Dating A Widower

1. They may be comfortable with someone their age

May-December pairings make for great romantic fiction. And yes, we know Leonardo DiCaprio has 19-year-old girlfriends, but he’s merely 46! In real life, a man in his 50s may be more at ease dating a woman closer to his age. Similar experiences, life journeys and cultural references can make it easier for them to connect.

That’s got a lot to do with what men over 50 want in a woman. They don’t just want hollow relationships or a trophy girlfriend/wife. They’re more likely to seek meaningful companionships built on mutual respect, understanding and support. For instance, a divorced man in his 50s has already been through the rigor of at least one past relationship and may not be keen on more trial-and-error in his personal life. He may just find it just easier to connect with someone he has a lot in common with, which can be harder in age-gap relationships.

Infographic on Men over 50
11 lesser known things women should know for men over 50

How to make it work:

It’s not set in stone that a man over 50 would always want to be with someone their age, but they may certainly lean in that direction. Here are a few pro tips that can help you make headway with that man who’s making your heart skip a beat, irrespective of the age difference:

  • Understand his dating goals and make sure they align with yours
  • Make him see how mature, level-headed and sorted you are
  • Work on building a connection with him
  • Give him room to figure out how he feels about you

2. Men over 50 are set in their ways

A friend of mine is dating a man in his 50s. A few months into their relationship she told me that he insists on wearing socks to bed, no matter the weather. He’s been doing it for 20 years and he likes it, so he’s not about to change. A person in their 50s is used to doing things a certain way.

Having lived on their own terms for a better part of their life, they know who they are and what they want. If you want more examples, remember that 90-year-old Warren Buffett has never spent more than $3.17 on breakfast. This self-assured sense of surety is a part of the appeal of men over 50 that attracts many younger women to older men.

do men over 50 fall in love
Both partners have to be flexible and accommodating to deal with past baggage

But it can also prove to be a double-edged sword. One of the biggest disadvantages of this tendency is that getting them to adjust and compromise can prove to be a struggle. If a man over 50 likes you, you might need to compromise a little. Also, consider that Buffett is worth an estimated $73 billion so maybe being set in your ways isn’t so bad.

For instance, if the man you’re with is a smoker, no amount of persuasion may be enough to get him to quit. Or you may find yourself struggling with getting him to change his eating habits, even if it is for the sake of his health. The key to making a relationship work is to strike a balance between respecting his way of life and not giving him a free pass on things that matter to you.

How to make it work:

Pushing to change can equate to pushing him away if you don’t know where to draw the line. Here’s how to navigate this tricky aspect of being with a man in his 50s:

  • Respect his lifestyle and choices
  • Remember he is an adult perfectly capable of making his own decisions
  • Don’t try to mother him
  • But also don’t let him walk all over you
  • Don’t sweat the small stuff
  • Pick your battles carefully, know where to stand your ground and which issues to let slide

Related Reading: First Relationship After Being Widowed – 18 Dos And Don’ts

3. They come with emotional baggage

Listen, men over 50 have already lived a full life. They’ve been around, had more than their fair share of heartbreaks and relationship challenges. All of this translates to emotional baggage. You can’t escape it.

If the man you have your heart set on has been single most of his adult life, he may have been through a crushing heartbreak in the distant past and developed commitment issues. In case he has lost his spouse, he may still be carrying some trauma from that event. If he is divorced, the drama with his ex-wife may have left him emotionally drained.

A friend, who is a lawyer, once told me she has a client who was paying alimony to his ex-wife till age 70. That kind of stuff is a heavy burden to bear. You too may have baggage of your own to deal with. All of this emotional baggage can make the possibility of a relationship untenable if both partners are not flexible and accommodating. In such situations, the ability to prioritize one another becomes a determining factor for the viability of a romantic partnership.

How to make it work:

Carving out a place for yourself and a budding new romance with a man in his 50s isn’t as challenging as it may seem, provided you keep the following things in mind:

  • Accept his life story for what it is, without judgment
  • Be understanding of his baggage
  • Don’t make it your responsibility to fix what someone else broke
  • Focus on your future together
  • Communicate about the future of your relationship
  • Take things forward at a pace you’re both comfortable with

4. They desire intimacy

Is a 50-year-old man sexually active? Has that question been weighing on your mind since you found yourself drawn to a man in his 50s? Well, you can rest easy on that front. Men do enjoy a healthy sex life at this stage of their life. But before getting intimate with your partner, it’s crucial to communicate your expectations. Are you both looking for a relationship? Or a casual fling? This is essential to protect your feelings as well as those of your partner.

Even if you’re on the same page, it’s advisable to hold off getting involved sexually until the sixth date at least. This allows you both to understand each other’s patterns and needs better. Whenever you do decide to get intimately involved, make sure that you practice safe sex. Just because you or your partner may be well past your fertile days does not mean that you’re protected against STDs and STIs too.

How to make it work:

Now that you know the answer to “Is a 50-year-old man sexually active?”, let’s focus on what you can do to make your sexual experiences as a couple as fulfilling as possible:

  • Communicate sexual expecations
  • Define and enforce sexual boundaries
  • Embrace your desire and allow your partner to be open about his
  • Don’t let his age hang over your sexual experiences

Related Reading: 12 Best Dating Sites For Seniors Over 60

5. Men over 50 may have problems performing sexually

Even though men over 50 enjoy sex, they may grapple with some problems or challenges in their sexual performance. Getting an erection at the right time and sustaining it long enough to be able to satisfy a partner in bed remains one of the top concerns of men over 50.

Besides, there may be some awkwardness about getting intimate with someone new after a long time. This awkwardness can adversely impact not just sexual performance but also their ability to enjoy the act. So, a man over 50 likes you and likes sex, but there could be issues, so be kind. He may not be able to articulate this (who at any age wants to admit they’re scared to have sex!), but you’re both at an age where you needn’t be coy. So, please go ahead and talk about it.

You can support your partner on this front by letting them take things forward at their own pace, without feeling pressured to get sexually intimate before they’re ready. A few encouraging words or gestures can also be a huge boost that can turn around your sex life for the better.

How to make it work:

The tricky thing about sexual performance anxiety is every subpar encounter can further fuel anxious feelings, which in turn impact the ability to perform, thus setting in motion a vicious circle that can be hard to break free of. Keeping that mind, here’s how you can navigate the hits and misses:

  • Never mock or make light of your partner’s inability to perform sexually
  • Be supportive but without coming across as patronizing or condescending
  • Don’t sweep intimacy issues under the rug
  • Be open to experimenting and taking charge in the bedroom

6. They may be conscious of their body

It’s true that Brad Pitt and Johnny Depp are both over 50, but most men don’t have the time, resources or need to look like that every day. There are handsome men over 50, of course, but most men’s health at 50 years old is far from what it used to be in their prime. These health concerns have an impact on the way they look.

An unsightly paunch, wrinkled skin, receding hairline are not uncommon at this stage. If you’re wondering whether men over 50 workout, a lot of them do, but age can catch up nevertheless. This can make men over 50 conscious of their bodies, even though the concern about how they’re perceived may not be as pronounced as it is in women.

These body image issues can impact their desire to put themselves out there as well as their confidence in bed. Complimenting your man about all that you find admirable in him can be a great antidote to this self-conscious attitude. “I love those broad shoulders” or “Your gentle touch makes me feel more alive” – such genuine and thoughtful words of praise can make your man view himself in a new light. And take it from us, a six-pack does not guarantee skill in the bedroom.

How to make it work:

As a woman, you know exactly how body image issues can wreck your self-confidence. So empathy and compassion are your biggest allies in tackling this situation. We’re here to help with some additional tips:

  • Be accepting of your man as he is, warts and all
  • Don’t point out his “flaws” even out of concern
  • Compliment him often
  • Be generous with your affection

Related Reading: Older Man Younger Woman: 9 Reasons Why Dating With Age Gap Works

7. They may be old-fashioned

The worldview of men over 50 is rooted in a time when chivalry was desirable. They grew up learning that they’re expected to make the first move, hold doors and pull chairs of their “lady loves”. While the world may have come a long way since, these old-fashioned ways may still be the norm for them.

And not just in the way they date, court or behave in relationships. Men over 50 fashion, eating habits, political and religious beliefs, cultural references may all be from a time when they came into their own. It’s unlikely that any of it is going to change now. So, your best bet is to accommodate their good old-fashioned ways as best you can.

If he wants to be the pursuer, let him. When he plans a date, tell him that you enjoyed his company and had a good time. Unless he says or does something that is downright outlandish, socially unacceptable or goes against your values, there is no harm in playing along.

How to make it work:

This can be a particularly tricky issue in relationships involving younger women and men over 50. While your worlds may seem poles apart sometimes, it doesn’t have to drive a wedge between you two. Here’s how you can bridge the gap:

  • Be at peace with who your man is
  • Give him space to be himself
  • Suggest healthier choices if you must, but don’t insist on them
  • Bring your worldview to the table, let him view things from a different lens
  • Steer clear of dad/grandpa references

8. They crave emotional support

Men over 50 may be from a time of machismo-driven stereotypes like “boys don’t cry” or “tears are a sign of weakness” but deep down they desire and crave emotional support. More than anything else, what men over 50 want in a woman is a companion they can share their most intimate thoughts with.

At this stage of life, most social obligations are taken care of and professional pursuits have pretty much plateaued. That’s why the need to have someone to share the day-to-day goings-on becomes more pressing than ever.

A man may feel lonely after a divorce, loss of a partner, or may suddenly find his single existence extremely lonesome. A man over 50 who never married could crave emotional intimacy. That’s also one of the reasons when men over 50 decide to start dating again, irrespective of why or for how long they’ve been single.

How to make it work:

Yes, men over 50 may crave emotional support but not know how to ask for it. The onus of building emotional intimacy may fall on you. Here is how you can deepen your connection, one day at a time:

  • Get to know your man better
  • Ask him questions about his life so far
  • But don’t prod if he’s not ready to talk about certain experiences
  • When he talks, truly listen
  • Open up to him and share your most intimate thoughts with him
  • Build up on your connection by prioritizing each other day after day

Related Reading: 15 Things Divorced People Should Know When Getting Into New Relationships

9. They won’t feel threatened by you

One of the most spectacular aspects of men over 50 is how secure they can be in relationships. A man who has lived a full life, complete with ups and downs, accomplishments and regrets, has no reason to feel threatened or eclipsed by his partner.

That’s why they won’t feel intimidated by smart, educated, successful and opinionated women. Quite the contrary. Older men appreciate intelligence in a potential romantic interest and are stirred by the fact their partner can challenge them every now and then. So, bring on your arguments and show off your successes to your heart’s content. He’ll appreciate it, and you.

How to make it work:

Well, his secure, self-assured temperament is one of the biggest assets of a man in his 50s. So, you don’t really have to do much on this front to make things work. However, it’s vital that your actions don’t make him feel like he’s being taken advantage of. Here are a few ways of ensuring that:

  • Be transparent and honest with your partner
  • Honor the promise of trust and loyalty
  • Don’t resort to petty mind games to get his attention. If you feel something is lacking in your connection, talk to him about it
  • Appreciate him for being a bankable support system
do men over 50 fall in love

10. Admitting mistakes can be hard for men over 50

It’s hard enough for men of any age to admit they’re wrong. But as someone who has built a life for themselves over the years and is used to living it on their own terms, men over 50 can tend to be a bit of a Mr. Know-it-all. Be it politics, social issues, weather or the right directions to your lunch destination, he might lead with the assumption that he knows best. Even if he doesn’t.

Also, a divorced man in his 50s could be carrying the baggage of having always been told he’s in the wrong in a past relationship and may have tired of it. Or maybe he’s a man over 50 who never married and never had to admit too many mistakes! If he is not right, making him see the error of his ways and admit his mistake can be exasperating. While it’s not the most pleasant thing to have to put up with, it is just a harmless irritant that grows on you over time.

How to make it work:

His inability to say, “Sorry, my bad” can become a source of chronic conflict in the relationship if not handled the right way. Here are a few ways to prevent that eventuality:

  • Pick your battles wisely or you’d be caught in an incessant loop of petty arguments
  • Don’t lose your cool when making him see he’s wrong about something
  • Come armed with facts and figures, he won’t back down easily
  • Never lose sight of the bigger picture
  • Know where to draw the line: do his views on global warming irk you enough to risk your relationship? If so, by all means, go in all guns blazing. If not, agree to disagree

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

11. They may hesitate in asking you out

Do men over 50 fall in love? Yes, they can. But whether or not they act on those feelings is a different story altogether. Blame it on the baggage of the past or having been off the dating scene for far too long, men over 50 may struggle with expressing their interest in someone new.

More often than not, this is a defense mechanism to protect themselves from getting hurt. A man who has suffered the pain of heartbreak in the past wouldn’t want to put himself in a vulnerable spot. Unless he feels it’s safe to do so. So, if you like someone in their 50s and get a sense that the feeling may be mutual, make sure to express your interest to him through your body language, eyes, words and actions. It might just be the nudge he needs to act on his feelings.

How to make it work:

If it seems like your prospects with this man in his 50s you’re crushing so hard on are in limbo because he just won’t make a move, it may be time to take matters into your hands.

  • Flirt with him in person and over texts so that he take a hint
  • Welcome him to dating in the 21st century by asking him out
  • Plan a stellar first date and knock his socks off
  • Focus on building a connection with him, so that you can draw him out

Single men over 50 are in a league of their own. While there are challenges to being involved with them romantically, the pros far outweigh the cons. If you can succeed in drawing him out and building a meaningful connection, it will be the most rewarding and fulfilling companionship you’d embark on.


1. What happens to a man’s body at 50?

At 50, a man’s body can be riddled with a host of health issues and medical conditions. Diabetes, heart conditions, weight issues, erectile dysfunction are some of the common problems men face at this age.

2. Can a 50-year-old man date?

Yes, of course! As they say, 50 is the new 30. As more and more people are living more wholesome lives, dating at 50 is no longer a rare prospect. A man in his 50s can be open to new romantic partnerships irrespective of the circumstances surrounding his single status.

3. How to get the attention of a man over 50?

A man over 50 is likely to look beyond physical appearances and outward charm in choosing a partner. If you want to get his attention, charming hin with your intellect and intelligence is the best recourse. Only when he feels that there is the scope of a genuine partnership based on mutual respect and support between you two will he want to take things forward.

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