30 Things You Need To Know About Dating A Man 20 Years Older Than You

In as much as age is just but a number especially when love is involved, here are 30 things you need to know about dating a man 20 years older than you.

By Auntrone89
30 Things You Need To Know About Dating A Man 20 Years Older Than You

Truths about dating a man 20 years older than you

Men and women end up dating for a whole lot of reasons. While some date for love, others date strictly for convenience. In fact, there’re many cases where men date women 20 years older younger than them. Again, this may be because of genuine love or convenience.

Their reasons for dating aside, there’re always specific common attributes appear to be synonymous with relationships with such age differences. Without further ado, here are 30 common things you’ll need to know about dating a man 20 years older than you:

1. An older man is more likely to be chivalrous

The only reason chivalry is dead is that the young men killed it. But this might not be the case when dating a man who is 20+ years older than you. As the dictum says, old habits die hard. And since older men were born and raised in an era where women were treated like the queens they are, it wouldn’t be strange for him treat you like one. He’ll most likely hold doors and pull chairs for you. Heck, your older man might even write you sweet handwritten poems just to cheer you up a little.

2. You’ll feel more appreciated when dating an older man

Being constantly appreciated is arguably the best thing about dating an older man. He’ll adore you simply because being with you makes him feel like the younger version of himself. At his age, your man is most likely to have matured. And since part of being mature dictates that he goes for exactly what he wants. This means your older man is with you simply because you are exactly what he wants.

He will, therefore, seize every opportunity to make you feel loved, wanted and appreciated. Your older man will always make every anniversary worth remembering. Unlike their younger counterparts, older men prefer showing appreciation now rather than later. Let’s just say it’s just part of that old school MO and leave it at that.

3. He’ll never waste your time

As part of being mature, never expect your older man to ever waste your time. As earlier stated, he knows what he wants and will not beat around the bush. If he makes a promise, he’ll make good on it or die trying. And if he can’t come through, you can always count on him making it up to you. In summary, dating a man older than you means you’ll never have to second-guess or question his love for you.

4. He’ll always shower you with unexpected, thoughtful gifts

It’s no secret that dating an older man comes with its fair share of sparks and among them, lots of unexpected by pleasant surprises. To him, the most valuable thing is that priceless look on your face whenever he surprises you. Simply put, seeing you happy makes him happy.

And for this very reason, your older man will almost always look forward to getting you something nice and unexpected. Note that older men dating younger men have been doing this for the longest time. That’s why you should always expect yours to do all he can to make you feel special.

5. Dating an older man might mean seeing less of your friends

In as much as the road to dating a much older man may appear rosy, I’d be lying if I said you won’t hit a few bumps on your way to happiness. Some of these road bumps may come in the form of some friends who prefer to “sticking to their lane”. And by “sticking to their own lane” I simply mean not associating with someone – you - who dates men 20 years older than her.

Thankfully, you’ll still have some friends who will stick by your side. If this ever happens to you, be prepared to lose some friends. A true friend is one who is supposed to be happy because of the simple fact that you’re happy.

6. His kids might or might not like you

When dating a man 20 years older than you who also happens to have kids, you’ll have to accept and embrace the fact that his kids might not like you. In some cases, your reception will be warm especially if all his kids want is for their dad to be happy. But if the kids see you as a threat, then it might take years for them to accept you – and that’s not even guaranteed. Some kids might even boycott your anniversary invitations.

7. An older man is a tad mysterious

A mature man is expected to not only be comfortable in his own skin but also to have mastered the art of seduction. Therefore, expect him to charm the pants off you not only with his charm but also with the air of mystery around him. In other words, you’ll never be able to tell what your man is up to most of the time and that’s most likely to make you fall in love with him even more.

At first, you might think he’s hiding something from you. But as you get old, you’ll understand that mystery is just part of the older man’s charm. But that’ll be later in your relationship.

8. When brunch turns to official dinners

When you start dating an older man, you’re likely to start having much more formal lunches as opposed to the crappy junk you and your college friends are used to. This is usually the case because he’ll prefer taking you to more formal or classier places instead of McDonald’s.

Your older man will also encourage you to start eating right and get healthy. This is so because you are a jewel in his eyes and wants to show you just how much he values you more than anything else.

9. He might not want to have kids with you

In as much as your older man loves you, chances are that he might not want to have kids with you. The reason why most men date younger women is so that they can relive their youthful days. And since chances are that the might already have grown kids either in college or working, all he probably wants is to kick back and enjoy the rest of his days with you.

That said, it’s always better to ask him if he wants in the initial stages of your relationship, you know, right before things get a little serious.

10. Dating an older man equals less partying

When dating a man 20 years your senior, you’ll somehow find yourself partying less and less. This is partly because he’s been there and done that – meaning such things don’t interest him anymore. And that’ll mean you’ll end up partying less probably because it feels hella awkward partying alone.

Instead, he’ll prefer taking you to basketball games, business after-parties or even better, invite-only themed parties. The earlier you prepare yourself psychologically, the better you’ll be at adjusting when the time comes.

11. Your older man’s ex or exes will hate your guts

When dating an older man who doubles up as a divorcee, you should always be prepared for a serious backlash from the ex-wife, or ex-wives. Jealousy has and will always reign supreme under such circumstance. Therefore, if you love your older man and want to be happy, always avoid his ex-wife or ex-wives at all costs.

And in the event of a snafu – which they are highly likely to cause -, then excuse yourself and walk away from the situation. You can simply never win against a bitter woman. And in the spirit of evading confrontation, you can start by NOT inviting the ex or exes to your anniversary celebrations unless you are planning on a backlash.

12. Your older man is likely to have health issues

Dating a much older man has its ups and – as the Curate Egg Hypothesis reiterates – also has its downs, both in equal measure. If this happens to be the case, then you are likely to find yourself either helping him with his pain medication or escorting him to the hospital to receive his arthritis treatment.

I’m not in any way saying this to depict older men as disgusting, it’s just that they have a much higher chance of having health-related complications. And this very reason, you’ll have to be ready and psychologically prepared for that. If it hasn’t happened already, then it’s coming sooner rather than later.

13. You’ll always feel powerful and desired

Many young girls dating older men have confessed to feeling powerful and desired. In most cases, that power stems from the older man being so drawn to her youthful beauty to the point of doing just about anything to make her happy. And this will include the constant complimenting, pampering and so on. Simply put, your older man will assume the role of being your knight and shining armor and that’ll make you feel like a powerful little princess.

14. Your older man will often struggle to keep up

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You’re way more energetic than a man 20 years older than you. And in as much as he won’t be too excited to attend the hot parties in town, he’ll always struggle to keep up the few times you force him to attend. And in as much as he’ll get on the dancefloor and try to impress you with some good old moves, he won’t have the energy to pull an all-nighter like he used to in his 20s.

15. You’ll be judged

The fact that the bible clearly states that “Thou shalt, not judge” won’t stop the populace from judging you the moment they realize you are dating a man who is 20 years older than you.

As unfortunate as it may seem, that’s just how people are. This means you’ll have to develop a tough skin in order to find joy in your relation, whether you’re dating for love or you’re simply gold digging. Cherish every vacation and anniversary like it’s your very last and you’ll find happiness. 

16. An older man can be your lover and mentor

If you’re dating an older man, then expect him to guide you in every aspect of your life. The fact that he’s lived his life and has seen it all makes him the right person to warn you against making innocent mistakes that might end up costing you later in life. It’s also for this reason that most young girls end up dating older men instead of wasting their precious time dating within their seemingly clueless and broke age group.

17. He’ll need help staying updated with the new trends

If you’re dating a much older man, you should be prepared to teach him a few things. In as much as he has a Facebook account, he might need some enlightenment when it comes to working his way around Snapchat. This will likely be the case when it comes to his playlist as well as the latest trends in fashion. Therefore, it would be so nice of you to step in and help because chances are that he’ll be too embarrassed to ask. 

Be nice and considerate.

18. Expect some sloppy sex

“The older the man, the sloppier the sex.” – Anonymous

Again, I’m not saying this just to be mean. This is a well-documented fact and I am speaking from a medical point of view. Our bodies weaken with age and for this very reason, it’s quite natural for an older man to seek some libido boost from Viagra or other less popular aphrodisiacs.

This might not be synonymous with all older men, but it is the case with most of them. That said, if you’re still willing to date an older man, then, by all means, start by lowering your bedroom expectations. Let him surprise you if he will, but chances are that he won’t. And don’t blame him, blame biology.

19. His age is likely to show on his body

Dating a man who is 20 years older than you can be fun until he takes all his clothes off or worse, his dentures. In as much as some men in their late forties, fifties or even sixties are still active gym goers, most of them just don’t have it in them anymore. Most men in that age group prefer kicking back, beer in hand and reminisce. And if their favorite pastime is drinking beer and eating beef, then, by all means, expect them to look the part.

20. The constant pampering will one day get old

Chances are that dating an older man will introduce you to a whole new life of nothing but pure glitz and glamour. In the beginning, the grandiose anniversary parties, the expensive banquet of flowers every other week and not forgetting the expensive bottom red high heels will definitely leave you awash with exhilaration.

But with time, you’ll get used to the flashy lifestyle and start craving the basic things such as his time and attention. Therefore, it’s better to anticipate this feeling because come, sooner rather than later. And when it does, you’ll start doubting everything in your relationship.

21. Your older man will remind you of your dad

A man who is 20 years older than you are likely to belong to the same age group as your dad. And in as much as he’ll try to act young and cool, he will always be a constant reminder of your dad and that can end up affecting you if you aren’t careful. The fact that he’ll always be quick to correct you and provide guidance will make things much worse. If all the above pisses you, then I wouldn’t advise you to date an older man because that’s definitely not your kind of man.

22. Chances are you aren’t the only one

Dating an older man is all fun and games until you realize you’re just one among a multitude of girls he purportedly “loves and adores”. It is, therefore, a smart move for you to not invest too many emotions into the relationship especially during the initial stages. You should give it at least a couple of months until you are 100% sure that you are the only one.

Waiting is nothing but a precaution you’ll be required to take to avoid ending up with a shattered heart. And while you’re at it, do a background check on your older man’s. If he had a promiscuous past, chances are that he is still promiscuous. Again, old habits die harder than Bruce Willis.

23. You’ll hardly argue

One of the many advantages of dating a man 20 years older than you is that he most certainly understands women. This means he’ll do everything in his power to not only make you happy but also avoid pissing you off. And whenever he makes a mistake, he’ll immediately apologize and make it up to you which will, in turn, avoid arguments.

24. Expect to travel a lot

As earlier stated, one of the many reasons a man 20 years you're senior is dating you is none other than to relive his youthful days. And for this reason, escaping with a much younger woman – you - would seem like a brilliant idea. And that’s how you’ll end up traveling a lot. You shouldn’t be surprised when you’ll most probably be celebrating each anniversary in different parts of the world.

25. He’ll definitely show you off

Your man will, sooner rather than later, start showing you off to the world. Simply put, older men get a kick out of dating younger, and definitely hotter women. So, if the younger, definitely hotter woman happens to you, don’t feel bad. Your older man does this simply because he loves you unconditionally.

Showing you off will also boost his ego and make him feel young again. So, the next time he takes you to formal dinners or to celebrate New Year’s or your anniversary in high-end places, make sure you are looking hella good for him.

26. Sometimes you may feel underestimated

Just because you are dating a man 20 years older than you doesn’t mean he’ll always be confident with your decisions. This is usually the case because deep down he still believes you’re still a young and inexperienced. If this ever happens to you, don’t take it personally. Just kick back and follow his lead. You might be surprised just how dating an older man might help you learn a great deal.

27. You might end up feeling lonely

Some girls dating men older than they often end up feeling lonely. This is because hanging out with older people makes them out of place. This is usually the case with younger girls who just wanna have unlimited fun and partying instead of attending long and boring after-parties with people discussing the economy instead of ‘getting it down’ and ‘turning up’.

28. He’ll introduce you to important people

Dating a man who is 20 years older than you can help your career especially because he is likely to introduce you to his connections. At this age, chances are that he has an impressive, sometimes enviable, resume which automatically translates to having a lot of important people on speed dial. You’ll also get the chance to meet these high-value members of the society when attending those long, boring after parties he’ll keep dragging you to.

29. You’ll receive competition from your peers

For reasons best known to them, some girls your age will envy your newfound happiness and try to upstage you in your own relationship. All the photos you are constantly posting on Instagram flaunting your lavish anniversary celebrations will get under their skin and you should, therefore, prepare for a backlash, sooner rather than later. Some of these envious girls might even be your friends.

30. You may never get to see his parents

When dating a man 20 years older than you, chances are that you may never get to see his parents. This is because of two things: one, his parents might be long dead or two, his parents might be still alive but won’t approve of you. Therefore, in a bid to keep his “happy bubble” intact, he might just want to keep you as his dirty little secret and hope for nothing but the best. If he introduces you to his old parents and they end up like you, you’ll be among the lucky few.


As we’ve already established, dating a man 20 years older than you has its advantages as well as disadvantages. It’s, therefore, a good idea to examine both sides as carefully as possible before making a leap into the unknown. Remember that every relationship is different from the next, meaning your experience dating an older man will be different from the others. And that’s why you shouldn’t get into the relationship blindly because chances are you might end up regretting it later.


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