Business, Friendship, and Money Etiquette

I have no problems with making sure that my purely personal friendships jive well when money’s involved; I pay my way and assist friends in need within reason, we’re honest with each other about our limits, and it generally works out pretty well. I have no problem with keeping my business money separate from personal money in a corporate environment, and generally dining out with the office has always been fairly straightforward: the office paid. But what of the gray area in between? Specifically, when you’re networking and not interviewing with or working for the person you’re dining with?

From a purely business perspective, my friend/mentor advised me not to quibble over who paid the bill when I dined out with an older, successful, networking acquaintance. “He can most certainly afford it, he invited you, and he can always write it off,” she asserts. These points were all true, at the time. The person in question is both gracious and helpful whenever possible leads come up, and has since taken the initiative to point me and my resume at highly placed persons who were interviewing for desirable positions. [At which point it’s up to me so that there isn’t impropriety or influence on my behalf which I would never ask for or expect.]

But what happens when the acquaintance morphs into a semi-friendship? When you’re meeting to catch up and tell stories, it’s no longer 100% business. I feel like that development then brings with it the obligation to offer to, and even insist on, paying sometimes. It’s only fair. I don’t want my acquaintance/now friend to think that I simply expect a great meal at his expense; that’s certainly not the case.

I’m aware that insisting on footing the bill when he has selected the restaurant, when he is more than financially comfortable [yes, finances have come up in the conversation in a career-related turn], and/or when I am unemployed seems to smack more of irrational pride than sense. But I’m unemployed, not destitute, and it hardly seems right to assume that I shouldn’t pay simply because I don’t have access to a corporate account. That seems like a recipe for brewing resentment; the line of reasoning that “you have more money than I, so let’s use your resources, thanks!” doesn’t sit well with me. Neither party’s resources should determine who pays. It can certainly influence the selection of the experience, but I think fair means that both parties take it in turn to pay.

How does the financial relationship change when your business relationship acquires shades of the personal? How should it?

[Disclosure: This post is also published at my blog, A Gai Shan Life.]

About Revanche

Revanche writes the personal finance blog A Gai Shan Life.