In The Book of Basketball, Bill Simmons has a footnote about a freshman gift gone woefully awry. In an apt comparison to the MVP vote for Wes Unseld, he recalls buying a half-dozen roses for a girl with whom he'd made out a few days before. Her reaction to the gift was so negative that he concludes a handful of plutonium would have gone over better; apparently she nearly left treadmarks running away from him.
Now, I once bought Spacebunny an expensive pair of quasi-steampunk designer sunglasses about two months after we met. Not only didn't she object, she was delighted with them and didn't lose any attraction to me as a result. So why would a cheap gift of a few dollars set off alarms when an expensive gift of several hundred dollars didn't?
Although my SMV at the time was higher than Bill's, remember that it was already established that the girl concerned was at least somewhat sexually attracted to him. And although my SMV was higher, well, SB's was almost certainly higher than Janine Cunningham's too. Because Holy Cross.
The reason, in retrospect, is pretty simple, although I didn't realize it at the time. You see, the reason I was at the store was because I was there buying myself a rather expensive pair of prescription sunglasses, a pair that subsequently drew comments from a game industry magazine.
"Besides sporting the de-rigor all black outfit of a game developer, Theodore sports shades - indoors mind you - that look like they're made out of titanium and probably cost more than the entire budget of the Gamasutra yearly booze allotment."
So, the shades I bought for her were correctly seen as an afterthought, rather than the pressure-inducing bid for commitment they might have otherwise been considered. And, in fact, they were an afterthought of sorts, since I simply thought they'd look cool on her and would kind of match my own ineffably awesome style.
Anyhow, it strikes me that if you want to buy something for a woman, the safest and most effective way to go about it may be buying something even better for yourself first. There is a massive status difference between offering up a gift in supplication and giving one that comes with the implicit message: "yeah, you're going to want to up your game if you're going to run with me."