My Gay Romance with an Older Colleague: a Silver Fox and the Pet Shop Boys
Funny how the ones who slip away leave lasting lessons — whether they intended to or not.
Picture this: I’m deep in the work grind, a random Spotify playlist going in the background. Everything’s routine until — bam! — the Pet Shop Boys’ “You Only Tell Me You Love Me When I’m Drunk” fills the room.
It hit me like a whiskey shot on an empty stomach — sharp, burning, and impossible to ignore. In an instant, I was transported back to the early days of my career, when life was a little more complicated and a lot more confusing. It took me a few months and this song to let it all sink in, but there I was — partly grateful, partly confused — trying to pull myself together for a client presentation the next day.
A few months earlier, one of my colleagues ran into an old coworker of ours. You know the type — silver fox, corn-fed and chunky, with that unmistakable Midwest solidity, even though he’d been settled here for years. He always carried that Midwestern charm and swagger, the kind of guy who could stroll into a room and own it without even trying. He left the firm years ago, but we’d parted on good terms. To my colleague’s surprise, he asked about me — curiosity never dies, does it? My colleague filled him in, casually mentioning that I was not only still with the firm but thriving. Oh, and that I’d come out as gay and was living my best life with my partner.
That’s when my colleague caught it — a flicker in those sharp, steel-gray eyes, like a crack in his otherwise polished exterior. He looked a bit stunned, like the thought of me being gay didn’t quite compute, shaking up whatever old-school notions he’d been clinging to.
My colleague figured it was that old-fashioned conservatism creeping in, or maybe it just blindsided him. “Either way, he got a good reality check, and I hope you don’t mind me telling him,” my colleague added, mentioning that despite it all, he genuinely seemed happy for me.
“Out of all the people he could’ve asked about, it’s interesting he asked about you.”
I shrugged it off, explaining that we’d worked on a major long-term project together — the kind that cemented our firm as the client’s go-to consultancy, and we still are, by the way. But just like that, memories I hadn’t dusted off in over a decade came flooding back, like flipping through a forgotten photo album.
To set the scene: I was younger back then — 25, more ambitious, and just starting to navigate the corporate jungle. He was older, with that polished confidence that comes from years of experience and a career that had seen its fair share of success. Smart, chunky, and mature? Honey, that’s a triple threat that never fails to catch my eye. Naturally, I was drawn to him — who wouldn’t be?
We did team up on a few projects — no power plays, no drama — just two pros who knew how to keep it buttoned-up by day, and as we got to know each other, maybe a little unbuttoned by night.
But don’t get it twisted — this wasn’t about any sketchy power dynamics.
He wasn’t my boss, we weren’t even in the same department, and he definitely wasn’t my project manager. Sure, we worked together, but it wasn’t your typical office cliché — or at least that’s what I kept telling myself. I was the one who made the first move, leaning in close while watching his screen, casually letting my arm and shoulder brush against his. The first time, he didn’t react — it was easy to pass off as accidental.
But the second time? He didn’t miss a beat in reciprocating.
Looking back, I can see how his subtle comments set the stage, nudging me to test the waters. He’d chuckle and say things like, “It’s a shame a sharp guy like you has to spend the evening with an old fart like me instead of being out with girls your age — I’m sure you’ve got no shortage of admirers.”
He’d also casually drop remarks like, “I really like the suit you’re wearing — you’ve got a good eye for combinations.”
Now, this was coming from a man who lived in top-tier Armani while I was in respectable but less flashy Brooks Brothers. In hindsight, I know he meant it as a compliment, but at the time, it left me feeling a bit underdressed, almost like a second-tier employee standing next to the polished professional. Those early comments, themselves always polished and professional, had a way of making me feel both uneasy and, in a strange way, out of my depth — almost as if he was subtly highlighting the gap between us, even if it was wrapped in a laugh or a smile.
As I got to know him better, I realized he was a “no bullshit” kind of guy — whether he was praising my work or offering what he liked to call “directional feedback.” He was never negative, though; he always framed it as areas for improvement, usually shared during our one-on-one conversations. He kept the focus on growth rather than criticism. And now, sitting here reflecting on this chapter of my life, I have to admit, I learned a lot from him.
For a year and a half, we kept it cool, discreet, and professional when it mattered. But after hours? That’s when things got a little more… interesting.
At the height of a large, intense project, the “benefits” were happening two to three times a week. Even after the project wrapped, we still met up occasionally, maybe once or twice a month, until he eventually left the firm. So while he laid down just one rule — “You can’t fall in love with me” — I was the one who set the rest. Despite his seniority in life, it became clear that I was the more experienced one when it came to man-on-man affections.
To be honest, he was a bit awkward at the start. So, I took on more of a teacher role, guiding him through our encounters. I guess it added a unique dynamic to our time together. No strings, no complications, just a bit of fun. And at the peak of our playing, I’d be lying if I said I didn’t catch feelings, even just for a moment. It was more than just the sex for me, at least in the start — my heart got tangled up in something deeper. But I never let myself believe it was mutual, or let him know that I was in it a bit deeper. Again, reflecting back now — I probably was in love.
And that’s where that Pet Shop Boys song comes back into play.
After a few stiff drinks, Mr. No-Strings would suddenly morph into Mr. Sentimental. “I love you,” he’d whisper, his voice soft and a little slurred, like he was letting slip a secret he wasn’t sure he should be sharing, something he usually guarded like Fort Knox. But come morning? Oh, honey, it was like someone hit the reset button. He’d brush it off, laughing it away like it never happened. And to be honest, I played along, teasing him right back as we laughed it off together.
It was maddening, absolutely, but there was also that thrilling rollercoaster appeal that kept you coming back for more. Now, I never really told him about my feelings for him.
I was young, a little naive in the workplace, and still figuring out my place in the business world — a stark contrast to my private life, where I was far from inexperienced. I knew who I was. He was married to his job — or so he claimed. I never got the full story. Did he have someone else? A girlfriend? A boyfriend? Who knows? He wasn’t exactly an open book, and I wasn’t about to push for details.
Our arrangement worked for what it was — a bit of fun, a bit of intimacy, and for him, nothing more.
When it came to his reaction toward my colleague, I knew it wasn’t old-school conservatism at play. Maybe it was regret, or maybe he was wishing he’d had the courage to step into his own truth, whether he’s bisexual, gay, or just stuck in the what-could-have-beens. For all I know, maybe he has come out since then, or perhaps I was just a chapter in his story — a way of experimenting before he realized that women were what truly lit his fire.
The attention from this handsome man helped me appreciate myself in ways I never had before. It also made me realize that my attraction to slightly older men — despite what my gay friends might have expected — was perfectly natural for me. Looking back, I hope he learned something too — if nothing else, how to become more comfortable in his own skin, to embrace life beyond work, and to truly enjoy his sexuality, regardless of which side of the fence he ultimately landed on.
Now that I’m just a few years shy his age when we met, I can’t help but wonder how I’d react if someone my age on my team started flirting with a younger colleague. Frankly, I wouldn’t stand for it. I’d step in right away because, even though I didn’t fully grasp it back then, I now understand that power dynamics can exist even without a direct line of authority in a business area or project.
While I’m still confident that it wasn’t a factor in my own “colleagues with benefits” experience, I believe I was an exception to the rule, or maybe I am still a bit naive. Call it double standard, but it’s one I’m comfortable with.
Looking back, I realize that while I was young and a bit naive in the business world, I was solidly grounded in who I was as an individual. I had a strong foundation, with unwavering support from my parents and siblings, which gave me the stability and confidence to navigate life on my terms. Just because I managed to handle that situation doesn’t mean I’d allow it to happen on my watch today.
People enter our lives for all sorts of reasons, and not all of them are meant to stick around. He was one of those — a fleeting presence who left behind a string of good memories, a strong work ethic, and a significant influence on my career. But now, years later, hearing that Pet Shop Boys song again brings it all rushing back. Funny how a melody can do that.
These days, the song doesn’t just bring back those old feelings — it reminds me of how far I’ve come and of the unexpected lessons this affair taught me. That wasn’t part of the plan, but I’m grateful for it. So here’s to the ones who slip away; their lessons linger long after they’re gone. Cheers to that!
“All of my friends keep asking me
Why, oh, why
do you not say goodbye?
If you don’t even try
you’ll be sunk
’cause you only tell me you love me when you’re drunk”- ‘You only tell me you love me when you’re drunk’ from Nightlife
