Someone on the Dollar Stretcher forums posted a link to this article in last week's New York Times: "How to Be Frugal and Still Be Asked on Dates." The upshot of it seems to be that although saving money has become a lot more popular and socially acceptable in the past couple of years, it's still widely seen as a turn-off in the dating world. In a way, this makes sense, if you think of the way our society has traditionally been structured: women of earlier generations had to marry to achieve financial security, so a man hoping to attract a mate would flash around his money to prove that he had plenty of it. Unfortunately, this strategy is likely to backfire, since a spendthrift mate is actually less likely to have money in the bank with which to support a family. It also creates a problem for frugal folks seeking partners with similar inclinations. Spending lavishly on your partner, as seems to be expected during courtship, is a good way to attract a mate with expensive tastes—not someone who's prudent with money.
Amy Dacyczyn wrestled with this problem in the first Tightwad Gazette book. She pointed out that a marriage is more likely to work out if both partners have the same views about money. Unfortunately, it's hard to find a frugal partner when society expects you to spend extravagantly while dating. So her suggestion to tightwads seeking same was to resist this urge, which sends the wrong message to potential partners, and instead put out "frugal date bait." Her examples include home-grown flowers, home-cooked dinners, picnics in the park, and for the truly adventurous, "tightwad dates" like an afternoon of yard-saling. With this type of "bait," rather than expensive outings and gifts, you're more likely to attract a mate who doesn't value a romantic gesture based on how much it costs.
Speaking for myself, I can honestly say that frugal dates and gifts are my favorite kind. It's not that I don't appreciate the occasional fancy meal or expensive present—especially coming from my fellow-tightwad husband, who never spends extravagantly on himself. But the little things, in their way, mean even more. One of the first "dates" Brian and I ever had together was a visit to a big sort of gallery/flea market. I tried on a dress at one of the secondhand clothing booths, and he admired it so much that he bought it for me—for all of $15. It was such an impulsive, romantic gesture that I cherish that dress to this day, even though I haven't been that size in years.