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The Case of the Twenty-Somethings

by | Dec 4, 2023 | Relationships, The Adventures of Dating

This one is going to ruffle a few feathers.

Someone I used to know once told me that I was trending. Recent research suggests that a rising number of younger men are seeking older women and vice versa.

When it comes to dating, there’s always been a double standard about age gaps. An older man who dates a younger woman is often applauded, while an older woman who sets her sights on a younger man is typically met with side glances and referred to as a “cougar.” As I have begun to date again, I have not written off the idea of dating men younger than me and have received plenty of these sideways glances. At first, I struggled with the idea of this kind of age gap, but a wise friend told me to get over it and take it as a sign that I still got it. Needless to say, this is new territory for me, and there have been very few dull moments as I have navigated my way through the idea of dating a pool of men that I had never considered before.

Dating a guy in his 20s can feel a lot like getting a dog. First, you’re floored by his cuteness. He can do no wrong, and every minute you spend together is fun and magical. Then, you realize he’s kind of high maintenance. He needs lots of attention, care, and cleaning up after. What’s more, the fun record seems to be the only one he plays. Most of the time, he’s totally oblivious to what’s going on and keeps chasing his own tail. Slowly, you begin to wonder: Is he worth it?

In your 20s, focusing on the fun parts of a relationships feels fine, and you’re not too worried about whether the adventures and good times will last. When you’re in your 30s, however, your perspective starts to change.

You don’t want a dog. You want a human being. Someone who acts like an adult, who can support you through thick and thin, and who’s willing to weather both the ups and the downs.

It’s not uncommon for men to “grow up” a little later than women, but I think that there’s often a reason for it — probably more than one. We don’t reject adulthood because we’re childish, we’re scared of the traumas we’ll have to face once we decide to give life our best shot. Having fun is a cover-up.

Like many of us, twenty-somethings may have never had a healthy relationship. Life is tough and so is finding love. Everyone has a hard time with it. Maybe, the “girls” he dated before you were immature, emotionally unavailable, or struggling with their own issues. He might feel extreme career pressure and a need to “be successful”. Society places expectations on men teaching them that they must be able to take care of the woman in their life and be the bread winner. It doesn’t matter whether their anxiety is rational or totally misplaced, it’s there, and it’ll likely affect your relationship. Especially if you’re a successful woman. And chances are, that if you’re dating a younger man, you will be further along in life. I am sure there are countless other reasons that might help provide context to the behavior of men in their 20’s, but I am not looking to write a book on the topic and am only sharing what I have learned throughout my experiences.

So, if you’ve ever felt a guy in his 20s acted more like a teenager and behaved unreasonably, my experiences have taught me that he was probably struggling with something and didn’t tell you about it. Or maybe he’s just an asshole. I am open to all explanations. Because here’s the thing, age doesn’t always equal maturity, and I have dated plenty of men older than me who have acted like toddlers. However, in addition to the twenty-something aged dogs I have foolishly shared a meal with, I have also met some really great twenty-something men too, and I am not ashamed to say that I will continue to be open to dating younger men. The pool is already so small to find the right person for yourself. Why are we making it even smaller? Men don’t.

However, a few words of advice. If you’re a twenty-something man looking to date an older woman, you better remember that you’re not chasing a girl, you’re chasing a woman and you better get it together if you want to stay in the game.

Allison Rose



Allison Rose

Founder at Filter Free Bullsh!t Free

Entrepreneurship is my addiction, Sharing my story and empowering others is my passion. My girl gang, my family and tequila shots fuel my soul & calm my head. I’m here to inspire and to be inspired.

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