I still cringe thinking about this one. It’s not so much a Winning Line, more of an aftermath.
I used to move around the country with my job. One particular contract took me to the Midlands, where I met up with an ex-colleague. We started seeing each other, all very casually, until things ended naturally when I moved to London
A few months later, I bumped into another ex-colleague from the same place.
We hadn’t spoken in a few years, so we were having a good chat about the old days.
Jen: “Do you ever keep in touch with any of the old gang?”
Me: “Not really. Oh, funnily enough, I was actually seeing Dave til quite recently.”
Me: “Yes, remember him?”
Jen: “Dave Edwards*?”
Me: “Yes, that’s him. You remember Dave, don’t you?”
Jen: “Yes. I’ve been dating him for the last three years.”
Jen: “Yes. Didn’t he mention me?”
Me: “Err, no, he didn’t.”
Jen: “He definitely didn’t mention me?”
Me: “Not once. I’m so sorry, I had no idea”.
And then came the most awkward silence ever in the history of silences.