How to Date a Younger Man in Your 50s – Things to Do in 2024

Dating younger people still tends to be a taboo topic among some men and women, especially when you are in your 50s.

Younger men relationships are not that popular among people who are in their 50s, and it seems like both older men and women still have some stigma around it.

How to Date a Younger Man in Your 50s - Things to Do in [year] 3

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However, if you decide to let yourself loose, enjoy the moment, and get involved with whomever you like, dating a younger man can really be a beautiful experience.

You are in the right place if you were asking yourself:

What things you should know before you start to date a younger man in your 50s
What you should do in order to keep him interested
Why is dating so hard in your 50s
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How to Date a Younger Man in your 50s?

1. Have Courage and Confidence

Mature women in their 50s usually don’t have the guts for younger man relationships, and they get discouraged easily, especially by women of their own age who don’t approve of this kind of dating.

If you want to keep enjoying your dating life in your 50s, too, you shouldn’t worry about the age-gap relationships, and double standards society tends to pressure on us.

Old woman dating doesn’t have to be scary, and women who like younger men shouldn’t be afraid to show it, whether they are 30 or 50 years old.

The key to becoming successful at dating at this age is in having enough courage to approach whoever you may like and being able to forget about the age difference.

When looking for younger men, the key to becoming someone who is alluring and interesting to them is to be confident and sure about your personality.

If you believe you are strong enough on your own and that people are naturally attracted to you, you will be able to make these men enchanted by you, even if they are 20 years younger.

This is also something that will be a lot easier to do with people who are outside of your age group because you will be able to make younger men go crazy for you much faster than those of your own age.

How to Date a Younger Man in Your 50s - Things to Do in [year] 4

Whether you are looking for a short-term (like BeNaughty or Ashley Madison) or long-term relationship (like eHarmony or Tinder), self-esteem is the most important thing, and it is definitely a game-changer when dating younger men.

Older women dating can go smoothly as long as you act like you are a high-value woman who knows what she wants in life and stays unbothered by irrelevant people.

If you have to courage to approach a 20-year-old man you like and you walk into the room like you are the one who owns it, 50+ dating will be very easy for you, and you will be able to make all these younger guys go head over heels for you.

2. Don’t Show Feelings Too Fast

Dating for women over 50 can get quite tough because of one specific thing – emotions.

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Young women are usually not that dependent on their feelings, and they can make rational decisions, but with older single women, things tend to be a lot different.

They are usually guided by emotions, and even though women share little to no information about their dating and sex life, you will be able to see what is at the root of her decisions.

If you want to be a real 50-year-old cougar, sleeping with a younger man shouldn’t be based on your feelings, and make sure to never make a mistake like this.

The more emotionally distracted you are, the better the relationship and sex with a younger man will be.

It doesn’t mean that you shouldn’t develop any feelings for the man you are seeing, but that you should try to keep it on the low and make sure you never express them to him, at least not before you are 100% sure it is reciprocated, and he is willing to stay with you.

Old woman dating younger guy usually tends to be very open about her feelings, but keep in mind that things that are considered to be a must-do when dating a man over 50 should never be done on younger guys.

They know that dating an older woman in her 50s is quite challenging, especially if they are someone who is pretty dependent on the things other people say about them, so make sure you don’t make things even worse by telling them that you love them.

Falling in love with a younger man should be very slow and easy, and you need to make sure you are the one who has control over everything, even though it may not look that way.

What makes an older woman crave a younger man is his adventurous spirit and lust for life and pushing him into something serious way too fast can completely ruin your potential relationship.

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For that reason, stay cool and never tell him how you feel before you are 100% sure he is the one who will stay with you at all times.

3. Don’t Talk About Your Previous Relationships

Old ladies looking for younger men tend to be very open, and from time to time, they can really overshare, especially when it comes to their previous relationships and marriages.

You should never mention how unsuccessfully your previous flings were, whether you were practicing casual hookups or were in a long-term relationship or marriage.

Things like this can sound way too scary to younger men, especially if you were married before, and it can really push them off before you have even managed to meet each other properly.

Younger women tend to be talkative about these topics too, but they were usually never involved in something too serious so they can listen to them talk about related stories, but when it comes to older women and their marriages, they are really not that tolerant.

Older woman-younger man relationships are already pretty challenging and messed up, so it would be best if none of you were mentioning your previous love experiences; otherwise, things can get quite tough.

As you probably know, this is also something you should never be talking about when you are on a first date with someone, and you shouldn’t even be mentioning during online dating chats.

Things like this can make you feel strange and uncomfortable around your potential partner, so it is best to keep the distance when it comes to things like this and make sure he is in love with you before you proceed to tell him more details about your life.

Also, I wouldn’t recommend mentioning the flings you had with other younger men because it can make them feel less confident and even used before the two of you have even started anything.

They believe that a woman in her 50s needs to be in love with a younger man before she decides to sleep with him or engage in a relationship, and you should keep them thinking that way.

When they find out that you have already dated another younger man and that these relationships were not that successful, they may feel scared and even run away because they don’t know what they can expect from you.

Keep everything on the low, and never mention your previous relationships, at least not too much – you can say that you were married, but never mention the reason why you divorced, and don’t talk about your ex-husband.

What Do 50 Year Old Woman Want In A Relationship?

Even though people will always ask is it weird for an older woman to date a younger man, that really isn’t something we should be bothering with because relationships like this are everywhere around us.

Rather than that, we should try to make it clear for both sides what are the keys to a successful relationship when there is a big age gap.

A younger man seeking an older woman will always want to find out how he can satisfy her, especially if he is dealing with a woman in her 50s.

This is a pretty big age gap, similar to that the French president Emmanuel Macron and his wife Brigitte have, so it can be quite tough to balance all the things out.

A 50-year-old woman dating a 30-year-old man, of course, wants some love and sex, but she also wants to feel understood and cherished.

More than anything, they want to feel like a human, and they want to be seen with all their flaws and loved regardless, so the best thing you can do for your older lady is to be gentle with her and allow her to process everything at her own pace.

The key to maintaining a successful relationship with a 50-year-old woman is in making her feel understood and thoroughly listened to all that she has to say.

These women are pretty open about everything, and you will definitely be able to solve all problems that may appear between the two of you in a matter of just a few minutes.

Listening is the key, and the things that will make these women feel loved and satisfied are way too simple for you not to be delivering it.

Does Dating A Younger Man Ever Work?

Don’t be discouraged by the things you hear from people in your surroundings or social media – an older woman dating a younger man can succeed as long as they are sure of their relationship.

For example, you have Priyanka Chopra and Nick Jonas, who have managed to enjoy their marriage even though millions of people across the world were against it.

If you feel like that man is the one, no matter how much younger he may be, you should go for it without thinking about the things other people may say to you.

Dating a younger man can work only if both of you believe in that and have enough trust in each other that you will be able to make things work out, no matter the obstacles.


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