In Wednesday’s discussion about how to live on less and love it, Steve left an interesting comment:

One topic I never see covered is “extreme finances” or even simple frugality in relationship to being single. I’m not talking about being a cheapskate during dinner, but maintaining a low-powered lifestyle while seeking a mate. Like it or not, first impressions count and first impressions are often based on superficialities, even by nice and otherwise deep people.

Yes, there is always the rare person who will not care if you drive an old car or live in a cheap apartment, but other people don’t see old cars and cheap apartments as choices for a well thought-out philosophy, but as indicators that someone does not have his life together.

Is frugality beyond a certain point something that is for married people only?

This comment prompted Ben to respond to me via e-mail:

This is something that’s been on my mind as I try to improve my spending habits while preparing to return to an active date-hunting, mate-seeking lifestyle.

It’s not just about dating, though — if anything, that’s the easy part; just say “hey, how about the park?” instead of “Let me treat you to Chez Expensivique.” The hard part is trying to live your whole life frugally without seeming a) cheap, or b) a loser. (”No, honest, I choose to drive this reliable older car, it’s not that I can only afford to crawl along in my grandfather’s half-dead Gremlin!”) Frugal choices can make an impression that you don’t want to make.

Most discussion on this topic seems to focus on “Don’t worry about what other people think,” which is hard when you’re trying very hard to make a very good first impression on those people so they’ll want to date you. After all, it’s one case where we really are being judged by others — and should care about what those judgements are. The only other response I tend to see is “here’s some cheap date ideas” — which, like I said, is the easy part. After all, even wealthy, spendy-type folks go for walks in the park.

These gentlemen have a point: how does one live frugally without looking cheap?

During my last week at the box factory, a potential customer dropped by to make a surprise visit. When I know that I’m going to see somebody I need to impress, I try to look halfway decent. But on that day I was wearing a ten-year-old sweatshirt with fraying cuffs and a fraying collar. I had on a beat-up pair of sneakers. There was no simple way for me to explain to this man, “Yes, I know I might look like a slob, but it’s for all the right reasons.”

In dating and business and day-to-day life, people do judge us by superficial standards. How do you maintain a frugal lifestyle without giving the impression you’re cheap?