Dating A Woman 20 Years Younger – The Top 13 Things To Be Mindful Of

Love and Romance | | , Writer
Updated On: May 6, 2024
dating a woman 20 years younger

“She’s practically half your age!” “You seem to be going through a midlife crisis. Are you all right?” “She’s just in it for the money.” These are some of the things you might hear when you are dating a woman 20 years younger than you. 

Chances are you may just be a little confused as well. Is it okay to date someone 20 years younger than you? Is the relationship capable of flourishing? Should you go forward with this?

Yes, yes, and if your heart is in the right place, yes! There’s no reason why you should be overthinking your prospects at love. Before you spend another moment thinking about things you shouldn’t, let’s talk about a few things you should know while dating a woman 20 years younger. 

Dating A Woman 20 Years Younger: 13 Tips 

Think dating a woman 20 years younger than someone is unheard of? Think again. George Clooney and Amal Clooney have an age gap of 17 years. Jason Statham is 20 years older than his wife, Huntington-Whiteley, and Emma Hemming is 23 years younger than her paramour, Bruce Willis. Still have questions like “Is it okay to date someone 20 years younger”?

Plus, Jennifer Lopez said men under 33 are pretty much “useless.” In a way, they’re just taking their time to mature. We don’t know about you, but if J Lo said it, we’re all sold. Falling in love with someone 20 years younger can happen to anyone, but it might freak a few people out around you when it happens to you.

To make sure you’re not left saying something like, “My girlfriend is 20 years younger than me, and now my friends won’t stop calling me Mr. Midlife Crisis“, let’s take a look at a few things you need to be mindful of:

1. Dating a woman 20 years younger than you? Prepare for different worldviews 

Well, how could they not be? Your fashion sense probably hasn’t evolved since the day you turned 27, and the only “pop culture” trends you’re aware of are the ones your girlfriend tells you about. 

Naturally, your views on a lot of things are going to be very different. As a result, you may even have wildly different future goals or a different way of looking at the world. Perhaps one of the problems with dating a younger woman can be that you won’t see eye to eye on a lot of things. 

The sooner you acknowledge and address that fact, the better it’s going to be for you. You know what they say about opposites, right? 

Related Reading: 11 Things That Attract A Younger Woman To An Older Man

2. You have to figure out how to dismiss the “sugar daddy” taunts

When you’re dating a woman 20 years younger than you, the people around you are going to be thinking the same thing. Some may say it to you, some may not, but they’ll definitely be saying it to each other.

Sometimes, the problems with dating a younger woman aren’t even with the relationship itself. They can often be with the chatter that surrounds them. When you choose to be involved in such a dynamic, you’ve got to learn to deal with the jibes as soon as you can. 

Our advice? Lean into it or kill the elephant in the room by addressing it early in the relationship. Nip it in the bud or don’t let what others say bother you. As your 20 years younger girlfriend would say, “Haters gonna hate.”

3. Don’t be insecure 

Don’t be insecure 
Establish a solid foundation for the relationship

Chances are if she’s younger, she has probably got a vibrant social life — complete with a bunch of boy toys. And chances are, she entered into this relationship almost assuming that you’ll be more mature about things than the rest of the boys out there. 

Hence, try not to let emotions like jealousy, insecurity, and feelings of mistrust get the better of you. Make sure you establish a solid foundation for the relationship early on. There’s nothing worse than a grown man who acts like a child. 

4. Hold on, is the foundation for the relationship secure?

While we’re on the subject, it’s a good idea to have a little think about why you’re in this in the first place. When you’re dating a woman 20 years younger than you, you might be swayed by the exhilarating aspect of it all. But is there a premise for a lasting bond here? 

Is there something deeper than the sexual attraction you may be feeling? Just like any other healthy relationship, yours needs to have mutual respect, clear lines of communication, a commitment to the future, trust, and support.

5. While dating a woman 20 years younger than you, don’t assume what she wants 

“There’s an age gap, so she must want me to be spontaneous and immature, right? Let’s get those Tito’s shots flowing, I guess it’s time to party.” Calm down, sailor. Instead of assuming what she wants and why she’s with you, talk to her about it. 

Falling in love with someone 20 years younger than you doesn’t mean you’ve now got to live life like those party freaks who never leave Ibiza. She probably loves you for the person you are, and assuming what she wants is just a recipe for disaster. 

6. Treat her respectfully 

Do you think you’ve now got to foot the bill for all her shopping and every date you go out to? Think again. Since you’re not Hugh Heffner and she’s not someone you have to take care of, make sure you don’t let it seem like you don’t respect her as an individual. 

Don’t patronize her and make sure her thoughts, opinions, ideas, struggles, and emotions are validated. Nobody’s saying you might not know a thing or two more than her, but since we’re not in high school, try not to boast about it.

Infographic on dating a woman 20 years younger
Things you should keep in mind while dating a younger woman

7. Benefits of dating a younger woman: You can teach each other a lot 

It’s no surprise that most of your interests are not going to match. You like whiskey on the rocks. She’s all hiking and camping. You want a T-bone steak. She’s all about that vegan beef. Common interests in a relationship are important, but it’s not the end of the world if you don’t have any. Instead of viewing it as a problem, view it as an opportunity to learn something new. 

Try to find a middle ground. The difference in interests only means you’ll get to tell her about a bunch of things she probably has never heard of before, and she’ll tell you about stuff you never knew existed.

You’ve decided to date a woman 20 years younger than you, showing an interest in her hobbies is sort of necessary for the relationship to thrive. 

Related Reading: 16 Pearls Of New Relationship Advice For Ladies By A Man

dating a younger woman
It as an opportunity to learn something new

8. Don’t go on a “back in our day…” rant 

Oh yeah, talk about ancient history. That’s surely going to get her going. Unless ironically, don’t flaunt all the “wisdom” you have garnered over your many years on earth. The minute you go into a rant about how things used to be when you were doing what she might be doing, she has already zoned out, probably scrolling through TikTok.

Is it okay to date someone 20 years younger than you? As long as you’re both adults and you don’t bore her to death, we’d say you’re good to go.

9. Learning the art of conflict resolution is a must 

Since you’re both in different phases of your lives, you both might have different interests, and you may not see eye-to-eye on a few things, which will invariably lead to some fights. But that’s not to say, however, that those fights have to spell doom for your relationship. 

If you’re dating a woman 20 years younger than you are, figuring out how to go about conflict resolution might just help you save your relationship from the cusp of destruction. Every couple fights, so don’t let a bunch of petty fights ruin the way you view your relationship. 

10. Be aware of the power dynamics 

Sure, you’re more mature, you might even possibly be more financially stable, and your experience might have taught you a thing or two. Even so, it doesn’t mean you’re always the one in charge. 

A relationship features equality, and each partner must feel a sense of responsibility. Unless one partner wants to be coddled the entire time, assuming the dominant role is basically like signing a death certificate for your relationship. 

If it ever feels like the power dynamics have shifted to an unfavorable degree, as they might in any relationship, having a conversation about it is the first step to addressing it. 

11. As is the case in any relationship, be honest and communicate

“My girlfriend is 20 years younger than me, and I faced a lot of stigma from society because of it. Though I wish it didn’t, the harsh words got to me and would often affect my mood. I only figured out how to deal with it after I told my partner about it, and we decided to work through my feelings together,” says Marc.

By establishing judgment-free communication, Marc was able to tell his partner about the troubles he was facing. Though it may not have been easy to admit such a thing to his partner, the fact that he communicated his displeasure helped him get over it. 

The importance of communication in any relationship simply cannot be overlooked. If there’s something that’s bothering you, you must address it immediately. Try not to sweep problems under the rug, your girlfriend is probably going to know something’s up anyway. 

older man younger woman

12. You probably won’t like her friends, but don’t be rude about it 

One of the benefits of dating a younger woman is the fact that you get to see the world from a different set of eyes. However, one of the problems with dating a younger woman is that you have a whole bunch of eyes on you, viewing you unfavorably or who you may abhor with all your might. 

You may get along with your partner perfectly, but you may have a problem with her friends. You might not understand their lingo, you’re probably struggling to keep up with the pop culture references, and you might feel ancient by the end of the night. 

Instead of being rude about it, however, try to maneuver around it nicely. Maybe even let your partner know through effective communication (see point 11), but definitely don’t be patronizing. 

Related Reading: 5 Things That Make A Relationship Work | The Basic Essentials

13. Keep the sexual chemistry intact by working on yourself 

If you’re dating a woman 20 years younger than you, the sexual chemistry is probably off the hook. To make sure you continue to pull your weight in bed, make sure you take care of yourself.

Sex isn’t really the only thing that should be motivating you to take care of yourself. In such a dynamic, there’s a very real concern that you’re probably going to face health issues sooner than your partner will. 

Now that you know all there is to know about dating a woman 20 years younger than you, we hope the petty issues don’t end up causing rifts between you two. As long as the decision to date someone younger than you wasn’t purely motivated by a midlife crisis, the points we listed out should be enough to keep things going well between you two. We’ll leave you two kids to it. 


1. Is it wrong to date someone 20 years younger than you?

As long as you’re both old enough to be consenting adults, it can only be wrong if you two think there’s something wrong with it. Unless you have an issue with the dynamics of your relationship, there’s no one else who can say what you’re doing is wrong. 

2. Is 20 years too much age difference?

Whether there’s too much age difference or not, it completely depends on how both of you feel about it. Is the age difference a dealbreaker, or just another detail that doesn’t really matter in the grand scheme of things? 

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