My Unexpected Office Fling

So there I was, in my late 50s, single and not really looking for anything more than a casual date every now and then. But life threw me an unexpected curveball when I started working at a new company where I met the most attractive colleague you can imagine, let’s call her Jane. She was just as into numbers and spreadsheets as I am, but there was something about the way she'd look at me over the cubicle wall that made my heart race. We hit it off right away with a couple of after-work drinks and before long, we found ourselves alone in her office one evening. She seemed nervous but also excited, probably just as freaked out as I was, thinking back on it now. It wasn’t something either of us would bring up outside that little bubble of secrecy. Anyway, the chemistry was undeniable. We kissed and things progressed pretty quickly after that. Over the next few weeks, we’d sneak into each other’s cars at lunchtime to make out or sometimes find an empty conference room to explore our attraction more thoroughly. It felt so risky, but also incredibly freeing, like we were kids again. Then came the day when I got a text from Jane saying she was moving departments and it would be harder for us to keep this up without getting caught. That’s when reality hit hard, I had been fantasizing about us being something more serious, despite knowing perfectly well that my age gap with her (she’s in her early 30s) should have kept me from even entertaining such thoughts. Our fling lasted a little under two months before the pressure became too much and I let her down gently. We agreed to keep it purely professional moving forward, which wasn’t easy given how often we worked on projects together. It’s been about six months now since then and while I’ve grown to appreciate Jane’s boundaries more, there are still moments when I catch myself staring at her from across the room, wondering what might have happened if things had gone differently.