5 Things I’ve Learned Dating Younger Men


“A 20 year old’s something serious looks very different than a 30 year old’s something serious.”

In 2021, its rare that men actually approach women outside anymore. I’m not sure if it’s because social media has made men socially shy or the fear of rejection has increased but it’s rare. When I do get approached, it’s typically by men 5 to 8 years my Junior. Yes, I am cougar in training. Well I should say retired cougar in training because after my last experience, I will no longer be dating men in their 20s. You see, I’m 32 but I don’t look it. I’m aging like fine wine thankfully. But I also have this theory that black women usually look the same age from 25 to 40. Think about people like Megan Good or Regina Hall or LaLa. These women are well into their 30s, Regina may be in her 40s but standing next to one another, they look the same age. But back to these young whipper snappers.

I tend to get approached by 25 and 26 year olds all the time. It’s like mind boggling. When a guy approaches me now, I just say “You’re 25 aren’t you” and I’m almost always right. At first, I was flattered. These young men can have women their age but they were looking my way. I thought “Let me give this thing a try”. I’ve dated at least a dozen guys younger than me. Unfortunately, none of them worked out but I did learn some lessons on the way. I felt the need to write about this because I feel that many women in their 30s and 40s will get approached by men in their 20s because they’re just more likely to approach. I wanted to point out some lessons I’ve learned from my experience for those ladies attempting to embark upon their cougar in training journey.

To be clear, when I dated these men, my goal was something serious. I haven’t causally dated in years and I always lead with that so the guy knows what to expect. I also don’t want to waste my time. These guys would jump in head first saying they’re all in and ready. Well, here’s what actually happened and what I’ve learned…

They’re Learning Themselves

I honestly didn’t know who I was until I turned 30. That’s because I began my journey to self-awareness at 28. It took years to actually start learning who Ashleigh was. I say that to say, you can’t expect a man in his 20s to know who he is or what he wants. That’s what your 20s are for; discovery. We all know men mature slower than us so their journey is like watching a sloth cross the street. This is okay though, we all have our own pace and process to growth. In my own experience, I learned that younger men haven’t developed a strong sense of self yet so I couldn’t expect them to know what they wanted because they were still figuring that out. Again, this was my personal experience. There is always an exception to the rule but from what I’ve seen,  this is common.

Their Commitment Level Can be Deceiving

In my early and mid 20s, my commitment level was all over the place. A lot of it was due to my focus and priorities. I prioritized education, finances, and fun and that’s how my life was lived. I finished school, had a job, paid my bills, but I also partied hard. I was young, single, with no kids so I didn’t really have to focus on being super responsible because I was enjoying life. I’m now in my 30s and my priorities have shifted tremendously. I’m more spiritually grounded, focused on the foundation for my future, and stability. Men in their 20s are prioritizing money, sex, and parties. Sex actually might be first on that list. Again, this isn’t a bad thing because they’re 20. But when paired with someone like myself, who has been celibate for almost 5 years, this isn’t going to work. What I saw was them claiming to be committed to the pursuit of me but quickly losing interest because I wasn’t giving them sex. Honestly, this doesn’t bother me because I’m the mature person who gets it even when they don’t. When they commit, they are actually interested. They just tend to have a short attention span. It’s up to me to be wise enough to understand this and not fall into the trap. They will sweet talk your panties down if you let them then quickly lose interest when they get what they want or if they don’t get what they want quick enough.

They’re More Willing to Chase You 

I’m not a man so I can’t speak to the why behind this, but the great thing about younger guys is their willingness to pursue you. In the beginning, they will be very consistent with taking you out, spending time with you, planning trips, etc. It’s probably due to their level of freedom because most of them only have themselves to worry about so that means more free time and more money to spend on fun. Honestly, this is why I dated younger for so long because of the rush I got in the beginning. Although they aren’t likely to stay consistent with this behavior, if you just want casual fun then a younger guy is perfect.

They are Led by Lust 

I mentioned that their priority is sex already but I wanted to revisit this. Men reach their sexual peak in their 20s. Women typically reach it in their 30s and early 40s. This is a biological fact, not just my opinion. So when I say they’re led by lust, there is science to prove it. This is why most cougars date men in their 20s because they are matched sexually. They can stimulate you sexually but if your goal is longterm, you have to really think about embarking upon this journey. I’m not saying they’re incapable of commitment because that isn’t true. I’m just saying their reason for commitment is typically consistent sex with a woman they enjoy. My goal here is to give you a little knowledge on younger guys so you’ll be well educated on how they operate if you choose to date a man in his 20s.

Easier to Read if You Pay Attention

Although these young whipper snappers are exciting and extremely charming, you can usually tell up front how serious they are trying to be. Even if they lie, you can usually pick up on gaps in their words matching their actions. If you’re not so focused on the fun and attraction, you can clearly see if they actually want you for something serious or just a fling. Most of the ones I’ve dated claimed to want something serious, and I believe they meant it. But a 20 year old’s something serious looks very different than a 30 year old’s something serious. There is generally a disconnect there so communication is very important. Be sure to listen to what they’re saying as well as what they are not saying. For example, I dated a guy and he knew I was celibate until marriage. He told me “I don’t see marriage for at least 2 years” which was him saying “Heffa, I’m not waiting no 2 years to have sex with you”. He didn’t call me a heft but you get my drift. Pay attention and understand what they can actually offer you and if that’s enough for you. Be honest with yourself so you can avoid wasting your time and allowing your feelings to be hurt.

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