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(Sergiy Tryapitsyn/Getty Images/iStockphoto)
(Sergiy Tryapitsyn/Getty Images/iStockphoto)

Should I dump my freeloading, backstabbing friend? Add to ...

The question

My best friend of 25 years is a freeloader. He overstays his welcome, eats and drinks more than his share and harbours no shame in allowing others to pick up the tab. He spends several evenings a week at my house watching TV because he’s too cheap to pay for a cable subscription. I have come to accept this and we actually make occasional jokes about his habits. But recently I have learned that he has said some disparaging things about me within our circle of friends. The most hurtful and ironic of these backstabbing remarks was that he feels I am overpaid in my current job. The fun is gone and now I feel nothing but resentment over his freeloading. I feel betrayed and I’m ready to press the big “Eject” button on this friendship. Any advice?

The answer

Well, of course it’d be easy for me to say “press that button” and I suppose that’s what 99 per cent of advice columnists and most civilians, e.g. your friends and family, might say.

But for one thing, I’m loath to urge anyone to end a friendship of any length, let alone one of 25 years’ standing, for anything other than a series of truly hair-raising, spine-tingling infractions. I’ve got friends of that vintage: They would have to do something heinous indeed for me to turn my back on them forever.

The other thing is, I’ve been on both ends of the transaction known as “mooching.” I had a cohabitation-type relationship go south on me in New York – the relationship ended, as a Hemingway character describes how he became bankrupt, “first gradually, then suddenly,” and it was as if I’d been in a shipwreck: I had no plans, no prospects – and no money. I stepped off the plane back home with literally a pocketful of change to my name.

I metaphorically washed up – bits of seaweed metaphorically clinging to me, bottom of my pants metaphorically ragged – on my best friend’s doorstep and he put me in his spare room. Did I mooch off him? To use another nautical metaphor, like a remora (those little fish that attach themselves to sharks with their suckers and live on the bits the sharks miss when they’re eating).

He had a sense of humour about it. I even put up a “Debt Clock” with a working arm that I moved whenever I borrowed a fresh amount from him. He could’ve squawked, sure. Instead, he was a prince, and may have saved my life – or at least helped me avoid having to move back in with one of my parents. Either way, he earned my eternal gratitude and loyalty.

The litmus test is: While I was under his roof, I was scrambling to get back on my feet. And those are the twin litmus tests for your friend: 1) Is he doing his best to become financially independent? 2) In the meantime, is he grateful for your generosity?

Doesn’t really sound like it. Not reaching for the tab is a big red flag. And it sounds like you’ve already tried to joke him out of his parasitical practices, but he’s impervious to your humour-bullets.

Basically, I think the only way to go with your freeloading friend is to sit him down and tell him how you feel: You’re tired of his mooching, and you don’t appreciate him saying nasty stuff behind your back.

Be blunt. Generally, I’m all in favour of circumlocution, but not in this case. The time to mince words has passed. He may squawk. He almost certainly will, since money is always a ticklish topic.

But because a) you were willing to end the friendship anyway, and b) you have cable and he doesn’t, it puts you in a strong negotiating position. If he says, “The hell with you,” say, “Okay, if that’s how you feel.”

If he does, let him cool his heels a bit. Let him marinate and muse on it all. Maybe it was time he spent a little time in the “penalty box” anyway, reflect on his lack of respect for the rules of the game.

I have a feeling that after a period of time he’ll come back to you (if only to see how Breaking Bad wraps up). If not, well, it’s a chance for you to be the bigger person and reach out to him. You don’t mention it, but maybe he’s having financial trouble. Maybe he’s not just “too cheap” for cable, but can’t afford it.

If so, maybe help point him to the right direction to gaining financial independence. Talk is cheap, right? In fact, it’s free! Keep your wallet zipped up and your lips flapping as you advise him on his career, picking up tabs, standing on his own two feet, etc.

I don’t mean to sound glib. I think you’d be doing your friend a big favour by dropping a little Burnsian “the giftie gie us to see ourselves as others see us” type knowledge on him. Because mooching, not reaching for the tab and backstabbing – that’s not a good look for anyone. He has clearly lost his “mensch mojo,” he has lost his way as a gentleman, and needs your help to get back on track.

What am I supposed to do now?

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