down the drainI try to get along well with everyone. While I may disagree with another’s opinions or find their behaviors distasteful, I don’t think there’s any reason we can’t be civil. But there is one person for whom I have an unabashed dislike. And as fate would have it she was working at the takeout counter when I went to pick up an order at a local restaurant.

To call the situation awkward is an understatement. But we managed to play our respective roles of “customer” and “server” and she rung up my order. Of course I later checked my Amex to ensure no additional charges had been pushed through, and fortunately my food was not poisoned. But I digress. She presented me with the bill and above the signature line was the tip.

My total was $11.34. But first… a little background is in order.

This woman was my roommate and we had a very dramatic falling out. Prior to that, I supported her financially for the better part of a year while she got fired from various waitressing jobs. It was always my hope that she would get on her feet, but what tips she made were never quite enough to cover the bills which added up to a $1,500 debt (At the time, that was significant money).

Things got worse over time. Her car broke and she never got around to fixing it. Of course she had mine to borrow. The jobs kept getting worse in terms of pay and she’d quit or get fired from each one after a month. Her cats got sick and she couldn’t afford veterinary care.

She never stepped up and took care of her own problems. When I didn’t help her, things fell apart even more. When I came back from vacation, I found a dirty sock and maggots living in the piled up dishes that had been left there since before I left.

Eventually the real problem surfaced: it was drug addiction and she was spending money she could have used to pay me, or for that matter treat her three cats, on meth. I found this out after she had a psychotic meltdown due to lack of sleep. That was it. I’d been charitable but I was being taken advantage of; not to mention that there are certain things one should never allow into ones home. So it ended there.

Quite badly I might add.

There are some situations where you look back and laugh at how silly they were. This is not one of them and after almost five years I still felt the same way. But my intention is not to simply share my roommate horror story—I had a real dilemma. How much should I tip someone who took advantage of my generosity?

It would have been an easy swipe to stiff her, and I doubt anyone who knew the situation would really fault me. It might have also been equally satisfying to leave a ten dollar tip. After all, I’m doing much better now and she’s stayed relatively static. But both ideas never really entered my mind completely.

Not knowing really what to do, I put an extra dollar on the bill.

In the end I don’t think my tip mattered either way. We write a lot about money on this blog and in the end this story boiled down to a measly buck. However it was probably one of the most memorable single dollars I’ve ever spent. Sometimes it’s not how much you spend but rather the intention behind doing it.

Given that it inspired this entire series on tipping etiquette, perhaps I should have given more.

If it were you and your worst enemy in that situation, what would you have done?

When not avoiding awkward situations at local takeouts, Mike writes Broken Cupid, a dating blog for gay men.