Setting up your friends is a minefield. Tread carefully

I've made a terrible mistake. I set up two good friends. I've since played the whole thing out in my head a million different ways, and I can't find a single way this ends well.

She is an absolutely superb human being, recently divorced, and he's an utter sweetheart who has been largely single, on and off, since we first met when we were about 10. They're both creative, interesting, outgoing people, so I was surprised they hadn't bumped into each other somewhere along the way already. Tinder is such a small town, after all.

The second I heard they were going on a blind date, all the consequences started to hit home. I hadn't thought this through.

For starters, nobody wants to picture two good mates hooking up in graphic detail. And according to my subconscious, apparently that's unavoidable. But my overactive gutter-brain aside, let's play this out from worst scenario to worst scenario.

Say they hit it off, fall crazy madly in love and hop into a serious long-term relationship. Brilliant, right? Well, no! Dandy for them, but what about me? Then I lose not one, but two single mates. And at my age, it's not so easy to find wing-women and wing-men you want to hang out with in dodgy places to fuel and enable bad decisions together.

And if they don't hit it off, things don't go well for anyone either.

I remembered an incident from about 10 years ago when I tried to set up a woman I met at work with a mate. One day we were new friends with all the potential of forever, the next it was over. It turns out my choice of partner for her really offended her.

She considered herself a nine, and judging by the match I chose for her, she thought I viewed her as a five, and that didn't sit well. Her feeling was that true friends should see you as a nine. I suppose you can always extrapolate how someone views you through the relationship choices they'd make on your behalf. Despite the fact that it simply wasn't the case.

Sure, he didn't have superhero looks or a million in the bank, but he was one of those truly lovely, interesting guys. It also struck me at the time that they had a lot in common, so I thought they might get on. She didn't see it that way. Setups are a minefield of offence and defence.

But back to my today friends and other possibilities for disaster. The first date could go really well for one of them, but not so great for the other. Setup Rules 101: you think you can avoid getting caught in the middle, but there's no way around that call the next morning where both want to know what the other thought of them. How the Grand Canyon do you navigate that tsunami?

In another potential parallel future, things go smoothly, they like each other, and they date for a month, a year, a decade, but down the line things turn, as they often do. Doesn't one person always get more hurt than the other? I will forever be the guy who got the ball rolling, the seed of the trauma.

In retrospect, maybe a casual bump-into-each-other would have been a better way across this minefield. Getting them in the same room, without mentioning a setup, then standing back and letting nature do her best work. But who wouldn't see through that in a heartbeat?

Maybe I should focus on setting myself up rather. Anyone got any good single mates?