How to Date 20 Years Older Women in 2024 – Can It Work?

Dating a woman who is a bit older than you can really be a challenge, but if she is more than 20 years older than you, then you definitely need some advice before you get into it.

Even though cougar dating is more popular than ever these days, it still seems like young men are not so sure of themselves, and they need constant reassurance before they decide to make the first move.

The older woman-younger man relationship can certainly work, but only if both of you are willing to work on it and invest your time and energy.

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Do You Really Want A Relationship With An Older Woman?

Before you decide to make the first move, you really need to realize whether you are capable of starting dating someone older or not because plenty of men don’t really have the guts for it.

You may be attracted to dating an older woman 5 years or dating an older woman 20 years, but if you feel the fear the moment you think about getting into a long-term relationship with them, then old lady dating isn’t for you.

Most men pursue older women dating because they find them to be easier victims of their seduction game, but once they realize they are getting in love with them, they decide to step out of the game.

You can say, “I love older women,” but you should make sure you never engage or promise any sort of serious relationship to them if you are not ready (like eHarmony or Tinder).

Why younger men like older women may always be a mystery to you, but please, try not to hurt other people in this process.

If you are 100% sure you want to get into a relationship with this woman and you don’t mind the age difference at all, then you should be open about it and sort out all kinds of misunderstandings that may happen with her.

Even if you have some doubts, you should tell her because women of old age also have a lot more life experience than you and they will certainly know to give you a good piece of advice.

How to Date 20 Years Older Women?

1. Find Common Hobbies

Dating someone 20 years older than you usually means that this person is in her late 40s or 50s, so she still has a lot of energy, and she is definitely willing to explore life with you.

Mature woman dating can get really fun because they certainly know a lot of interesting things, and if the two of you have some similar hobbies, you will definitely be able to get along well.

You can go out to different social gatherings, visit all sorts of parties, exhibitions, and happenings and overall enjoy life.

This woman can basically become your best friend, and it is definitely a lot easier to get along with someone who has reached a significant age in life than with a younger person who still has no idea what she actually wants in life.

If the two of you are interested in similar things in life, then she may be the right one for you, and you should definitely do everything that’s in your power in order to make her stay with you.

Always recommend eventful outings and spend as much of your free time as you can together because not only will you be able to meet each other better, but also create a special bond over the things you love doing.

This is always a good recipe for any relationship, and when there is an age gap between partners, it will definitely make things a lot better.

2. Be Confident

Dating a man 20 years younger is not a problem for these women, and you will definitely see it from the beginning.

They have a lot of confidence and don’t really care whether the people will start gossiping about them or not because it is their life, and as long as they feel happy, they don’t feel the need to justify their actions to anyone.

If you want to overcome these age-gap relationships and become a mature man for yourself, then you should definitely learn to form her about confidence.

Make sure you are inspecting every step she makes and sees how it is to be the most confident person in the room without sacrificing your personality.

These women know they are not gold diggers and that you are not their toyboy, so they really have no problem with showing their relationship to other people, and you should be acting that way too.

Look at the famous couples, for example, like Nick Jonas and Priyanka Chopra – no one cares about the age gap between them because they don’t care about it either, and you can see how confident and sure of their marriage they are.

This is also very important when you are presenting your woman to your friends and family because as long as they see you are sure of your choice and that you really love her, they will keep all the negative comments to themselves and eventually become happy with your decision.

3. Work on Your Sex Life

This 20 year age gap is really not that big, especially if you are dating a woman in her 40s or 50s, and trust me, these women still have a lot of energy in bed, and they are not afraid to show it to you.

Many men claim that they had a lot of amazing sex with women of this age and that women in their early 20s can really never satisfy you like them.

You may feel taken aback by the fact that she is “20 years older than me”, but in general, these women have a wealthy sex life (like BeNaughty or Ashley Madison), and they definitely know some things girls of your age don’t.

I would recommend being very open about your wishes and desires but always allowing them to be the one who is dominant.

After some time, you will definitely see she is the best lover you have ever had, and most men say that they would never engage in sexual activities with younger girls again because the things older ones can provide them with are indescribable.

4. Never Treat her like an Old Lady

If she starts feeling old in your company, then you can probably forget about her for good, and with this approach, you can also forget about the older-younger dating too.

The moment your woman starts feeling like she is even older than her in your company, she will replace you with someone else and forget about you for good.

They know that dating a younger man in your 40s or 50s can be a bit challenging, but they have no respect for men who treat them like they are their moms and consider them to be old ladies just because of their age.

Even though they know they are not hot 20-year-olds, they still don’t want to be treated that way, especially by a man they find attractive and potentially consider getting into a relationship with.

Sometimes these women tend to be a lot more lively and excited about life than younger girls, and you should really treat them that way if you want to say one day, “Oh, this older woman likes me.”

They don’t want to say, “My boyfriend is 20 years younger than me” because they already know that, but they rather want to feel like the two of you are of the same age.

Always make sure you treat her with kindness and respect; otherwise, you may lose her before you even get into something more serious.

5. Compromise

Compromising is a big part of all relationships, whether you are dating a woman 10 years older, 20 or 30 years, or someone of your own age.

Since there is an age gap between the two of you, you will definitely need to make some decisions together, and things will not always be completely black and white.

For that reason, before you make any sort of decision that may impact your relationship, you should sit down and have a good talk – once the two of you come up with what might be the best solution, go for it.

Relationships like this tend to come with much more obstacles than regular ones, but as long as the two of you have good communication, and you are not afraid to have a serious talk and solve everything together, you definitely won’t have problems.

Sometimes you may seem like you are not able to find any sort of solution to your problem, and that’s fine, but you will need to make a compromise and do what one of the sides wants.

The next time, you may do things your way, but in general, you should be aware that it is very important to talk everything through before you decide to make a decision.

If you see she is vulnerable when it comes to a certain topic, let things happen her way because there is probably a reason why she feels like that.

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