Pros and cons of dating an older man

We help you decide whether you should go for that silver fox

Older men. Younger women. A love affair we’ve been scrutinizing and pondering over since the beginning of humankind. In this article, we give you all the pros and cons of dating an older man.

The pros

The pros can be summed up with more stability, both economic and emotional, better sex, a bigger dedication to the relationship. On top of that, there will be a general sense of gratefulness from the man in question.

The cons

The cons can be summed up with a “been there, done that mentality” that’s far from inspiring. Choosing an older man, you might end up with a patronizing partner who is set in their own ways, doesn’t blend in with your friends, and is not getting any younger.

Make an informed decision

In the best-case scenario, the relationship between an older man and a younger woman is a win-win situation, with both people feeling grateful for the unique partner they’ve found. In the worst-case scenario – it is a recipe for years of unhappiness.

We don’t want to end up being one of those bitter loveless couples slogging through life, one argument after another.

May-December Celebrity Marriages

Looking at celebrities, there are many examples of love affairs between older men and younger women. We rarely get a glimpse of the ins and outs of these relationships. All we get is a paparazzi photo with a smiling couple, some gossip here and there, or yet another break-up story.

Some examples:

George and Amal Clooney, age difference 17 years. It is hard to argue against the cuteness of those Clooney twins.

When it doesn’t work out

Michael Douglas and Catherine Zeta-Jones, age difference 25 years. They separated in 2013 after 13 years together. Rumor has it that it wasn’t the friendliest of departures. Check out their story here.

Ally McBeal knows how to do it

A couple that still appears to be going strong is Calista Flockhart (the quirky lead of the TV series Ally McBeal) and Harrison Ford, age difference 22 years. In an interview with Closer Weekly, Calista opened up about their relationship success: “Harrison and I laugh a lot, and humor is everything to me.”

It sounds like a great recipe for any relationship, but we are unable to ask Calista how she really feels about the age gap and what she would put on her list of pros and cons with dating an older man.

Is age just a number?

Often couples claim that age is just a number, that they fell in love with their partner’s personality, not the age. However, since you are here, looking through my list of pros and cons of dating an older man, I take it that such statements do not entirely convince you.

Perhaps you feel like you need some guidance, or you want to know what to expect. I have dated more than my fair share of older men, so you have come to the right place for advice on this topic.

Let’s do a playful evaluation

There are valid reasons to stop and think before letting someone with a solid pension fund, a house, and the possibility of paying for nice holidays, sweep you away.

Do you recognize yourself?

A warning before we dig in, we will approach this subject with fun and many generalizations. Not everything I say will resonate with your current situation.

But as time goes by, I’m sure you will discover that there is more truth to my words than you would like to admit. Such is the force of human predictability.

If you, on the other hand, want a playful article about the pros and cons of dating a younger guy, we tell you everything you need to know.

The pros of dating an older man

1. Stability

An older man means more stability. The older we get, the less we have to prove to the world.

A young man is often consumed with pursuing his dreams or figuring out what he wants to do and achieve. It is all about him. An older man, on the other hand, has already done a lot and discovered that some of the things he longed for in his youth were not what he had expected.

Instead, he settled down and went for stability. He has already figured out what is working for him. That is where you will find him, and he will welcome you to join him in that place.

A young man is still figuring things out

Another version of a young man is a dude who is just hanging around smoking pot and playing video games all day, confused about himself and the world around him.

With an older man, you would (hopefully) get someone that has already achieved some form of success. Older men are more comfortable with their place in the world and thus able to offer more stability and predictability.

2. Commitment

The next advantage ties into the first one. Young men are famously hard to pin down, always thinking they might find someone better. An older man knows that it is not the case. He has already tried and failed with that strategy. He has played the field. He knows that being single is not as fun in real life as portrayed in TV shows.

He is more likely to be satisfied

Thus, an older man is much more open to settling down. This is especially true if he meets a younger woman. He is wise enough to know that this is his golden ticket. The one he should lock down before she changes her mind.

3. More money

An older man will have more money. There is no denying that this is an important perk, so let’s throw it out there and savor the taste of it. More money means more fun. But that’s not the only reason why we should regard this as an advantage. Money is important. Not because money itself is important, but because of what money can buy: nice experiences and plenty of free time to enjoy those experiences and each other.

Money brings a lot of advantages

The safety that comes with having money is another big bonus. Money makes life nice and secure. This is especially important if you want kids. A lot of stress in romantic relationships stems from money problems. Choosing an older man means that you will be in a better financial situation.

4. Better sex

Sex will be better. An older man is more comfortable with his sexuality. And even better, he is comfortable with your sexuality. Younger men can be clueless, selfish, and finish quickly. An older man has had a fair number of women educating him.

He knows what he is doing, he has a couple of great tricks up his sleeve, so lean back and enjoy. He is a man who knows what he is doing and who is not afraid to take the lead. That kind of confidence comes with years and is sexy in the best possible way.

He will work hard to make you happy

An older man will be eager to please you. The older the man gets, the more interested he will be in making sure that he brings pleasure to his woman. He will go above and beyond (literally) for you.

He knows you could get someone younger and hotter, and he will be grateful that you have chosen him, and his gratefulness will translate into a very giving approach when it comes to your sex life.

5. Gratefulness

And this leads to the next benefit on my list – gratefulness. He will appreciate you just as you are, he will notice all those natural things that make you glow next to him: your smooth skin, the fact that your hair is not gray, and most importantly, that you are not bitter.

You won’t even have to put in that much of an effort to be appreciated. You will feel special, and in return, you will make him feel special. Since you are doing something out of the ordinary, he will spoil you as if you are the main character in a cheesy chick flick.

You will always be the one with the looks

You won’t have to wonder if he finds you attractive. You will know that you are the attractive one in your union. He will praise his lucky stars for having you in his life, and you will be the one that gives him all the sweet blessings.

In your union, you will always be the hot young one, regardless of how long your relationship lasts. That’s one of the heaviest arguments in the “pros and cons of dating an older man” -list, according to my experience.

The cons of dating an older man

1. Been there, done that

You are not exactly entering uncharted territory here. Dating an older man means that he has more experience than you, both in and out of the bedroom. All those sweet sexual experiences of his are wrapped together with other special experiences. First house. First marriage. First child.

He did a lot of things already before you came along

He has already had a lot of firsts. Someone has already done all those milestones together with him, long before you came around. In some cases, even before you were born. This can lead to bitterness and jealousy, or at least some form of lack of enjoyment.

There is a special magic to doing something for the first time with your lover. That for of magic you won’t always have the chance to experience with your older lover.

2. Patronizing

An older man can, unfortunately, be condescending. This character trait has an ugly way of becoming extra apparent when the two of you are fighting. Even when everything is great, it’s not fun to be around someone who thinks they know more than you do.

Some older men are terrible know-it-alls, as you probably know. And that is a quality you probably don’t want in your partner.

You will always be the one with the least life-experience

Think about how you sometimes feel when you hear someone ten or twenty years younger vexing about life. Do you think they sound a bit idealistic, maybe naive?

You almost want to pat them on their back and tell them that everything will be alright, that they don’t need to take things so seriously. This is going to be what your older man feels toward you from time to time. It might not even be what you say.

Your opinion will not be as valid as his

Sometimes our judgment is shadowed by the context. Just the awareness that your opinion doesn’t have the backing of his life experience will make it less valid in his eyes.  

He will not take you and your opinions as seriously as he would someone else’s of his own age. He knows better. In some cases, this will be true, but it’s not fun to hear that, especially in a romantic partnership.

3. Set in their ways

The older we get, the more set we become in our habits. Your new man will have a routine. And this routine is going to be something he is very proud of. After all, it has taken him many years to perfect it. When it comes to grocery shopping, cleaning, holiday making, cooking…you name it, he knows best how it should be done.

You might have to do more of the adjustment

Hooking up with an older man means that you either won’t have any possibility to shape his ways, or the room for changing his routines will be very limited. You’ll have to learn to adjust to his life, not the other way around.

4. Not getting any younger

Older men are only getting older and older… And one day, you will look at him and no longer see that hot man you got together with.

Instead, you will see just another grandpa, leaning over the crossword puzzle, listening to the radio, with some breadcrumbs caught in his beard. And you will wonder if those great years were worth it?

He will slow down

He will be old long before you. He will move slowly up and down the stairs, and he might even need you to help him. A sobering picture. Worth taking some time to contemplate.

Age means more the older we get

As the years pile on, the age gap will have a bigger impact.

While you are still young and probably want to enjoy life’s adventures, holidays, and fun parties, the number of things he can or wish to do will become less and less. Not to mention that there is a possibility of illness and, eventually – a death.

Yeah, this one aspect sucks, and you should make sure you take it into consideration when you do your own personal “pros and cons with dating an older man” -list.

5. Don’t blend in with your friends

No relationship is a lonely island. You might be doing great when it’s just the two of you, but life also involves friends and family. Your parents probably won’t be delighted. And even if he is wonderfully charming and wise, he belongs to another generation.

And get along with your parents

You might be shocked to realize how much in common he has with your parents. There is nothing sexy about concluding that your dad actually looks young compared to your new boyfriend.

You will need to compromise

On top of this little problem (after all, most of us don’t spend that much time with our parents), he might not fit in well with your friends.

The two of you might be on the same level, but it won’t be the case with all your friends. And vice versa, hanging out with his friends might not be as much fun as hanging out with people of your own age.

6. He might want different things

This is true every time we enter a new relationship. You might want to travel the world, he might want to stay in and work in his shed. He might be ready for children, you might want a career first.

He is at another stage in life

Every relationship takes a bit of adjustment, but we won’t need to consult statistics to know that when entering into a relationship with someone much older, you will have to be ready to accept that they’ll want different things.

We all go through different phases in our life, but in most cases, those phases are synchronized with our peers.

Make sure you are on the same page

So, make sure that the two of you talk through your expectations and how you would like to see your life unfold. How we spend our days and what we wish for in the future are some of the most crucial points to look at to figure out if the relationship will be successful.

In conclusion

Older men are great. They are wise, charming, and sexy.

There is something boyish and, at the same time, mature about them.

Certainly, there are many benefits to dating older men, and who else, if not me, would know about all those perks? But there are also some serious considerations to be made before falling for the older man.

What are you prepared to sacrifice?

Only you will know what exactly you are ready to sacrifices for your silver fox.

In the end, it’s up to you to decide which argument triumphs over the other on the “pros and cons of dating an older man” list.

Just make sure that he is the right man for you.

Check out our article on How do you know if you are dating the right person? to see if your relationship has a future (regardless of the age gap).