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Dating Someone Younger: The Good, Bad, and Awkward

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You meet a guy at a barbeque and you instantly connect – before you know it you’re discussing your favorite restaurants in the neighborhood where you both grew up and your mutual love of Breaking Bad. He asks you out. You say yes. The twist? You learn that he was in Junior High School when you were graduating college.

This exact situation happened to me last summer; and then again six months later. I’m in my mid-thirties and the younger men I dated were between 6 and 10 years my junior. Although neither relationship worked out long term, they were both eye-opening experiences. I’ve since learned that dating someone younger – whether it’s a couple of years or a couple of decades – can definitely work. However, being the “older person” in a relationship comes with it’s share of pros and cons.

Thinking of dating someone younger? Here’s a few things to keep in mind.

  1. Less life experience usually means less emotional baggage –

One of the really great things about dating someone who is younger is that they likely have less emotional baggage than people in your age group. One of the things that attracted me to Younger Guy #2 was that he seemed nearly devoid of relationship baggage. Although he’d had serious girlfriends in the past, he wasn’t hardened or jaded by these experiences. After dating a series of single dads and divorcees, my own age and older, it was truly refreshing to date someone who didn’t have a lot of previous relationship baggage.

  1. They’re sweet and being with them makes you feel like a teenager again.

Because of their lack of previous relationship experience, being with them makes you feel a bit like you’re living inside your very own Katy Perry song – all butterflies and giggles and Teenage Dreams. They’re sweet and romantic, and do things like pick you wild flowers on their way to pick you up. Enjoy it!

  1. You’re at different stages in life –

Lack of life experience is a double edged sword. While you may enjoy the fact that your date is more young and fancy free than their older counterparts, it’s important to be cognizant of the fact that they’re likely at a different stage in their life. For example, whereas you’re already settled into your career and are looking for something serious, they may still be dipping their toes into their profession and exploring different relationship options – or not. Everyone is different. Whether these differences make or break the relationship all depend on the situation and the people involved.

  1. They might have a different concept of what constitutes a good night out –

My idea of a great date night usually includes drinks at one of my favorite wine bars, some good conversation and maybe taking in a concert or an art show. While dating Younger Guy #1, I started to seriously question my life choices when one night, he suggested we fill up a couple of water bottles with booze and head over to the local rec centre to go swimming while getting drunk in the pool. When I pictured getting tipsy within the overheated, chlorine fume filled confines of the same building where I took childhood swimming lessons, I couldn’t imagine anything worse. The lesson here: your younger date’s idea of a good time isn’t necessarily going to jive with your own – in fact, it might make you outwardly cringe.

  1. When you realize you have completely different cultural references it’s….awkward.

I’ll never forget the moment when Younger Guy #2 asked me, “Who is MC Hammer?” These kinds of moments will happen. Brace yourself.

  1. Sometimes it will feel like you’re speaking a different a language –

In the case of one of the younger guys I dated, he abbreviated everything. In his words, sometimes it was totes awk when I had no idea what he was talking about. Hanging out with someone younger can sometimes make you feel like you’re speaking to a text message or living inside an Entourage script. True story.

  1. They keep you feeling young –

Awkward generation gaps and moments of immaturity aside, dating someone younger is fun and will help bring out your youthful side. For example, if I hadn’t dated Younger Guy #1 I never would have even considered going to a giant music festival this summer (something I’ve always thought I was too “old” to do, but which my date encouraged me to try.) Dating someone outside of your typical age range and can push you outside of your comfort zone – in a good way.

  1. It’s just a number –

When Aaliyah sang “age ain’t nothing but a number” she was telling the truth. Age really is just a number. I’ve realized that when it comes to relationships, a birth-date is rather arbitrary. Age doesn’t necessarily predict whether someone is going to be mature. As I’ve learned, the 23 year old that I dated was infinitely more mature and a much better communicator than guys I have dated in their 40’s. It’s all relative, so remember to keep an open mind.

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