Dating Someone Younger Than You: 12 Ways to Make It Easier

Do you have a crush on someone much younger than you? Read on to see how you can successfully date someone who’s way out of your age bracket!

dating someone younger than you

There’s something sexy about dating a younger man or woman, isn’t there? It’s taboo and risky, and you just may be the envy of all of your friends. But buyer beware: you may also be the laughingstock!

The subject seems to be cropping up on Dr. Phil and in the celebrity world more and more these days: massive age differences. Celebs like Nick Cannon, Demi Moore, George Clooney, and Julianne Moore have all dabbled in the world of dating a younger partner–and some of these matches even ended in wedding bells! So, what does it take to make a successful go of a relationship when your partner’s way out of your age bracket? As anyone who’s ever dated someone younger can attest: it takes a lot.

How to date someone younger than you

Read on to find out how to approach dating, and the practical mindset you should have before you undertake the scary task of dating someone way younger than you.

#1 Read their signs. So, you’ve thrown out all your best hints to your younger love interest and she seems to be taking it well. But is she really into you, or just politely flirting back to avoid awkwardness? Use your intuition and make sure you know for sure that she likes you, before you make your big move and ask her out.

#2 Weigh the pros and cons. Before embarking on your new adventure together, sit down and maturely weigh the pros and cons of pursuing your newfound romance. Do you have children who are your potential new mate’s age or older? Will your age upset their family or social status? Have you both considered the social difficulty and possible ridicule you’ll receive? It would be wise for you both to consider the potential pitfalls, and whether you are honestly up for the challenge.

#3 Have your first date in neutral territory. If you have it bad for your new flame, but you still aren’t sure if you’re up for the hassle, try having your first few dates in neutral territory, where your date won’t run into some college friends, and you won’t worry about running into your ex-wife, children, or colleagues.

#4 Have fun. Even if things don’t work out, you are trying a new experience and learning from someone with a worldview completely different from yours. Embrace this change and view it as a positive opportunity, no matter the outcome. [Read: 20 ways to have the perfect first date conversation]

What you need to know before dating someone younger

Let’s say you’re still on the fence when it comes to actually pursuing someone younger. What do you need to keep in mind?

#1 You may not have a lot in common. This seems like small beans, at first, but before long, the idea of you asking if they remember a certain TV show or this particular singer may have you cringing when they ask, “Um… who?”

You may start thinking, “Oh yeah, you weren’t even born yet.” Don’t let this discourage you, however. While you might not have a lot of common interests, you can still agree on or at least communicate about the important things, such as compassion, the treatment of others, religion, politics, and social issues. [Read: The pros and cons of dating a younger man]

#2 They won’t be as clever, worldly, or wise as you. Sad, but true. You may want to say, “But she’s wise beyond her years!” or “He’s really mature for his age!” While both may be true, that still doesn’t mean they are smart people. You’re dating a girl wise beyond her years? She’s still only 18 and, smart as she may be, she doesn’t possess the life experience you do, nor will she ever reach your exact level.

#3 Other people won’t like it. While we live in a world that has become highly understanding of age differences in couples, once the age difference goes beyond 10 years, people tend to start raising eyebrows. Is she a gold digger? Is he looking for a cougar and easy sex? What could you possibly have to talk about? “This is a shallow relationship that isn’t going anywhere.”

At least that’s what your friends and family might say.

Although your family may not say these things to your face, the likelihood is that they will at least think them. Unfortunately, people can be cruel and judgmental. Just remember that it is only you and your mate who really know the inner-workings of your relationship. [Read: 5 ways to deal with judgmental people]

#4 You need to know what you want. If you’re dating a much younger man, you need to know what you’re in it for. Are you looking for young, energetic sex, or are you looking for an actual relationship? If your answer is the latter, then you need to make this clear to your partner, before you start to get in too deep. [Read: 7 signs you may be being used for the wrong reasons]

#5 Act your age. Sure, you’re dating a 20-year-old… but please don’t think you must begin to act ten years younger than you are. Your younger girlfriend may want to drag you to clubs, and really, who are you to deny a little booty-shaking action?

Just remember: you already lived your 20s, and would you really ever want to go back and do it all over again? Most likely not. Enjoy your time with your new lover, but don’t let their age make you regret yours.

#6 You may get insecure. While dating someone younger may start to make you feel like you’ve shed your years, gained some energy, and acquired a renewed sense of adventure, it may also start to make you feel like an old has-been. Keep in mind: while you’re not as enticed by the age of “selfies” as everybody else is, you still have something to offer your relationship.

#7 You have a past and so do they. You may think that, as the older party in the relationship, you’ll be the one bringing all of the baggage into your relationship, but don’t underestimate the pressures and emotional issues that a 20-something goes through in this day and age. Don’t be surprised if your new beau brings a host of their own issues into your tryst.

#8 Don’t hide it. If you’ve gone past your first couple test runs as a couple with great success, there is no reason why you should hide your relationship from your friends and family. It may come as a shock to them at first, but with time comes change. Once they see you’ve been together a substantial amount of time, they’ll begin to trust your new mate like you do.

[Read: 50 compatibility questions to ask your younger partner]

If you have patience and understanding, and can let your guard down and let loose, you’ll have a fun time with your new mate in no time. Take it one day at a time and don’t be afraid to try new things. The possibilities of your new relationship are endless.

Liked what you just read? Follow us on Instagram Facebook Twitter Pinterest and we promise, we’ll be your lucky charm to a beautiful love life.

Waverly Smith
Waverly Smith is a freelance writer who has been getting paid for spreading her sarcastic take on love, life, and sex since 2010. She is many things that people...
Follow Waverly on