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The Fantasy of Dating an Older Man

couple_mixedage2It is commonplace in today’s society to have age-disparity relationships.  In the straight world many men like to have an attractive younger lady on their arm, and many younger women have walked the well-trodden path of having an older man as a husband as the benefits are obvious: established career, home, money and status.

In the gay world those attractions are still the same. However, over the last few decades another factor has come into play.  When the HIV and AIDS epidemic that wiped out many gay communities, younger guys considered dating someone from an older generation with the impression that they had escaped the virus and would be protected from it.

Also, in the adult film industry there has been a massive increase in Daddy-Son films, and this has in turn created a bigger market for older guys. And the popularity of older men has increased hugely as this kind of relationship has moved from the realm of fantasy into something to actually aspire towards.

As a gay man, through my dating years I personally focused on dating older guys. I wasn’t interested in dating anyone around my age.  Academically and career-wise, I was established and my finances were healthy, I liked to be around like-minded people, and I discovered a fertile ground of older guys. Growing up, in school I’d always been attracted to older men. They carried themselves differently, and had a confidence which was more solid, more reality-based, than the bravado of my counterparts. My first sexual forays were with guys of the same age, but I was often disappointed.  Yes, there was the excitement of the chase, and the desired outcome was always satisfactory, but something was missing.  So I upped the dating age group.

From there I was pleased with the pickings. Many men who had lived lives which were exciting, thrilling and had come through the ups and downs of life, now sat, as I saw it, in an established and comfortable life.  They had their style, and knew what worked for them. None of them were dashing off to the fashion boutiques to wear the ill-fitting and uncomfortable clothes that were on the trend of the moment.  I felt in my element, and the sex, wow the sex, that was mind blowing.   Many had clocked up enough mileage to know what worked; they had been there and got the t-shirt.

Through my dating life I met, dated and had relationships with guys much older than me, the oldest having a 27 year age gap.  While I was establishing my status in my chosen career rather than running with the crowd of party scene gays, I was being shown the nicer things in life, traveling to foreign lands, enjoying quality restaurants, and being introduced to wonderful like-minded people — not just hopping to trendy beach club resorts, bars and the burger joints of my peers.

I can hear you shouting already, “you were a kept man”, but that is not true. I covered my own costs. It was the seasoned company I was attracted to, not the financial benefits.  However, there were plenty of younger guys who were cashing in on the generosity and not putting their hands in their own pockets.  Let me tell you, these guys do not hang around, and even though they think they’re onto a cash cow, they are treating the older guy as a commodity and quite happily brag about it.  But these users are equally an easily-replaced commodity and can just as readily be treated as disposable items by their older companions.  They forget that older guys have experience, maturity, and have been around, so they’re not stupid or gullible.

Dating older men gave me a blueprint on how to live my life, how things were to be done, showing me things that my parents might have told me. But rather than having the parent/child dynamic, I had a mentor as well as a skilled romantic partner. And I could see positive results in my social life, career, and general quality of life by following their lead.

Throughout my dating years in my 20’s and early 30’s, I continued with my older guy dating blueprint.  With the population growing older and living longer, that meant I was never short of a date. Eventually, however, the dating dynamic just didn’t seem to work for me anymore.  I was now established in my career, home life and general status, and I didn’t feel like I needed a mentor anymore. I was one of the gang. Rather than looking up to someone, aspiring to be one of them, I was one of them.  I’d been emulating them by pretending to walk in their shoes; now I was wearing my own shoes and walking the same path.  In addition, as I neared the age of 40, dating someone within my previous age increments would have meant dating someone over 60. I think this was the wake-up-and-smell-the-coffee moment for me.  When I was a teenager and through my 20s, dating a guy in his 40s or even early 50s wasn’t that different.  But as I got older, dating someone in their 60s didn’t have the same appeal. Yes, I have gay friends this age, and for some, that age difference would still work. But something for me didn’t quite fit anymore.

I tried reverse dating, dating a younger guy. This was a monumental failure. I have huge admiration for older guys who put up with such immaturity and outrageous behavior.  I found myself saying, “In my day, we didn’t do things like that.”   This was a true sign that I had changed.  I know you can’t let one bad situation ruin them all, but for me it didn’t work. I could have persisted and tried a different guy, but it wasn’t for me.

Would I have settled down with a guy the same age as my parents? I don’t really know. Possibly.  But in fairness, although I had relationships with some truly wonderful and amazing guys, the thought of something permanent didn’t really cross my mind.  I was swept away with the experience, like going off to University and learning so much you are positively bursting with enthusiasm to experience more.

Last weekend I turned a corner and became middle aged. I reached the age of 40, but I  woke up in the arms of my husband of four years.  Is he older than me?  Yes, but only three years my senior. The path I trod in my younger years was a revelation, and it was wonderful. And I have age-disparity relationships to thank for where I am.  The knowledge and experience I was introduced to by these older men makes me forever grateful and appreciative.


Jonathan WelfordJONATHAN WELFORD heads up, a relationship and dating coaching practice. He was awarded the accolade of being one of the top 10 Gay Relationship Bloggers for 2013. He writes gay advice columns for numerous publications in both the UK and USA, and is also a regular columnist for He lives with his Scottish husband in Manchester, UK.


  1. David G /

    And it works the other way around too. I’m 49 and seeing a guy in his mid-20s. He’s already got his career under weigh, so he’s not really looking for guidance from me in that area, but he says he likes my “grounded” view of life and that I know so much about everything. (Got him fooled there, ha ha!) And we enjoy each other’s company. He makes me feel younger, helps keep me in touch with new things around that I wouldn’t have paid attention to before, new music, trendy off-beat places to hang out, and he likes to tell me what clothes to buy/wear. LOL. We are not thinking “marriage” at this point. We are just having fun. And I feel 10 years younger.

  2. Matt Williams /

    Right! I met John at a party thrown by mutual friends. He’s 55 and I’m 30. I just saw him across the room, and something inside me jumped. He was so f**king sexy and had this terrific smile. I got my friends to introduce us. I was too chicken to do it myself. And we talked the rest of the night. Then went back to his place, and spend the night on his couch, talking, kissing, touching. It was amazing, not like anything I’ve felt with guys my own age. We’ve been dating for 6 months now, and like you said, the sex is amazing. Whenever we’re in bed, it feels like my body is on fire! And it’s not just “sex”, he is so romantic and affectionate and thoughtful, it’s more like really making love. When we’re together I just feel so much safer and comfortable and alive. He hasn’t asked me to move in with him yet, but I would have to think twice before saying yes or no if he did.

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