dating older men

I’m pretty certain that the title of this blog post caught your eye. Now that I have your attention I can let you in on a little secret. This post actually focuses more on dating older men (5 years plus) opposed to those of pension age. I knew the title would reel you in so since you’re here you might as well read on and enjoy this collaboration between myself some of my readers, peers and loved ones.

The JWV brand loves personal truth and promotes transparency. So it is my hope that you’re able to take something insightful or valuable away from this piece, enjoy.

I’m in love with a man, nearly Twice My Age,

Don’t know what it is, but its a hit from mi youthful days,

As I go my way, I don’t care what people say,

I’m in love with a man, nearly Twice My Age!

In the beginning

I remember hearing that infamous Shabba Ranking song on numerous occasions as a little girl. I’de do the voiceover for Krystal’s part being sure to hit every single note. Belching from the top of my lungs as I played carelessly around the house.

Looking back now I didn’t have a clue what I was saying. But it makes much more sense as to why Aunty Lorna would often cut my performances short. “Go and pick up a book or find sumtin fi clean” 🧽and in response I’de roll my bigs eyes behind her back and then follow her instructions.

Growing up I was around men who were much older than me. Living on the Myatts field estate and having an older brother (Marcus) who was quite popular was the main reason for that. It was pretty normal and made me feel as though I had a big extended family. Not to mention having the constant presence of both my Dad and Stepdad in my life. All of that combined made me perceive older men as a source of protection and love especially as it pertained to family.

And they call it Puppy Love

But that didn’t stop me from developing a few crushes on men who were fell outside of that category. This included Rappers, Singers, Actors, one or two older guys from the neighborhood. My mum described those spells of Puppy Love as a healthy part of my development that she made sure to keep a very close eye on. So many of the crushes I had back then went no further than my imagination or inside the pages of my Girl Tech Password Journal (If you know, you know).

dating older men

However, when I hit secondary school and started to sprout out in key places many things changed. My mum no longer allowed me to play out on the estate and when the mandem came to see Marcus I had to be way out of sight. I didn’t get it but her reasons why really changed the way I viewed older guys from that point. According to Aunty Lorna age was more than just a number. Mummy also told me that older guys only wanted young girls for one thing and that was to take advantage of them and if I knew what was good for me I’de keep myself to myself. West Indian parents have a way telling you things without further explanation. So I took that as a warning and made of it what I could.

Hearing something like that at 11years old with not much life experience made me very weary of older guys. When they would holla at me I’de literally pay them nothing but dust. But as I blossomed into my teens and grew into my curves so did the attention of older guys. Luckily for me I learned how to navigate around that by talking to guys my own age. Many girls in my school got acquainted with older guys from young but I’de prefer to hear all tea opposed to having any to spill.

What the streets have to say

For years there have been conversations as to why women date older men. Those relationships appear to raise more eyebrows than men dating older women. The research into this topic is extensive and findings have done nothing but provide us many different answers.

Some say it’s related to daddy issues, perks, stability, attractiveness, more life experience and a long list of other things. What I do believe is women who date older guys do so for all types of reasons. There are so many contributing factors as to why. But who better to explain and share their experiences than women who have been through it. Read on for personals memoirs from some women who have dipped their toes in the older men dating pool.

Don’t do it sis


Would I recommend dating an older guy?

Nooooooo way!

Unfortunately the father of my children is 9 years older than me and he has to be the most immature person I’ve met in this life! Older guys seem to think they know it all but they know nothing. Most older guys have mummy issues that’s why they go for younger girls. If you want to be a mother before your time then go for it!

If you don’t stay well away! Mind games is something that they like to play and turning you against your family. As they’re older they manipulate you into believing you should only rely on them. Before you know it, he’ll have you where he wants you and you’ll be shut off from the outside world! Now not all older guys are like this but a majority of them are. When it comes to maturity I’ve found that guys my age or those slightly younger are ahead in that department. Older guys feel like the world owes them everything and once they get you on their side you will start to believe that this is a way of life!


My First Love

Rose Bae

I was in my first year of college so I was either 18-19, we were friends before that and we started dating. We dated for 3 years or close to it. I learned that we mature faster than men because even though he was five years older he still was uncertain about life, his identity and our relationship was at an important time in both of our lives. 

While I was studying he was moving from job to job, trying to find himself. I encouraged him to find something he liked and stick to it, he did but it was a process. A lot of what he went through I went through later in life and it was through being with him I understood what I was going through and I was able to be easier on myself.

Don’t get it twisted

Women think that older men are different and to be honest, the age is just a number. It depends on their lives and how quick they grow up. But also emotional maturity is something that doesn’t change with age but experience.

Overall it was a positive experience until we broke up. I haven’t seen him in over ten years but I don’t regret the relationship. I had fun with someone who was my best friend and my first love. We did everything we wanted to do with no regrets. To women seeking to date an older man, go for it. If you’re in your 30s, no one except you cares how old they are. If they make you happy and they possess everything you want in a man – then do you!


You’re My Little Secret


I was dating an older man about 2 years ago. At the time, I was 23 and he was 49. It only lasted for a few months. But I ended up moving in with him and finding out that he was hiding a lot of things. Like a whole girlfriend that I knew nothing about. Until the day she came to visit from out of town. To make matters worse he brought her to the house to introduce us all and I was heartbroken. I couldn’t even confront him about it because my best friend’s uncle. We were both living with him after moving to Atlanta until we got out own place.

Due to his age, I had expected him to be more mature and respectful about the situation. That’s when I realized that age doesn’t determine maturity. A childish man is a childish man, no matter the age. We had a big falling out and it made things awkward in the house but, I had to hide it because of my best friend being there.

While with him I didn’t have to work or pay bills and he offered great support/advice. I guess that was what attracted me to him at first and the more I got to know him, the more I liked him. I won’t say that I loved him because that wasn’t the case but, there was definitely a strong attraction.

Plot twist


Once we moved out of his house, I did a background check on my current boyfriend to be safe and thought I might as well do one on him as well. I found out that he is a registered sex offender with charges for child molestation as far back as 2011. I’m glad I dodged that bullet because if things further I would’ve been even more hurt to learn that he was hiding that as well. For that reason I’ve crossed older men off my list.

I will be 25 this year and my boyfriend who is the father of my almost born child will be 31 and our relationship absolutely beautiful. It really just shows that it’s about the quality of someone and their character as an individual. However, I just want younger women to know that just because a man is older doesn’t mean he will be any better than a younger man. Us women need to be cautious about who they choose to date. In saying that I’ll never judge a man based on his age ever again.

Older Men are it, that it’s, thats the message

So I’ve got both sides of the spectrum as my current partner is younger than me. Anyone I’ve dated prior to that has been older. I love an older man! They take responsibility, tend to spoil you and give you the good good in the bedroom.

But I wouldn’t recommend dating a bum of an older man. It’s the worse thing that you could possibly do especially if as they tend to come with kids.

My ex is 4 years older than me and we when dated I was a young adult, he was my first and he thought I was much older than I actually was, he also didn’t know that I was a Virgin either. But he knows now and till this day we’re still cool.!


A Newbie In The Game


I was 20 at the time and I didn’t have much dating/relationship experience, he was 30. 

I would say I pursued him as we started talking but I was more on the “I Want To Be With You Vibe”. Each relationship is different and that experience set me up to realise for the next 2 after what I wanted/required from a man . I’ve always been a mature girl but that’s because of the things I’ve experienced. Talking to guys my age, I’ve always felt like they weren’t ready or I was forcing them to be in the relationship I wanted not them. 

Overall dating an older guy was positive, he taught me a lot about myself, before him (& even a little after) I realised I always settled for people. Even with friendships, I’d always hold back myself because people didn’t get me. But I look back now and think “He Did Get Me”, which allowed me to look at myself differently, treat myself better and see I deserved better than I was allowing myself to have.


Never say never

From what you’ve read above it clears that dating an older guy is somewhat like eating a Kinder Surprise. As I enjoy the last few years of my 20’s I’ve played with the idea of dating older men but haven’t got very far. If I ever decide to give it a go the man needs not to have a Wife, Fiancee, Girlfriends, Situationships or a bag of kids. Also if his affairs aren’t in order then he has no business being in any relationship with me. Plus he can’t be over the age of 33 and if he is he can’t be older than 35. Unless…………..

Stay blessed

Lots of love



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