Let me say it once and for all: There is nothing "naughty" about a woman ordering a piece of cake.
I've been a waitress. I know it's rough, and you develop weird shticks, and a lot of customers probably respond to the whole "co-conspirator" approach to dessert ordering, the sly proffering of the dessert menu, the impish wink of the enabler, otherwise it wouldn't be so common. But. Trying to "tempt" me or winkingly insinuate that there's something naughty about getting a piece of cake or generally carrying on as though we're somehow putting something over on someone by having a sweet is offensive. Because you know what? There's nothing particularly "decadent" or wild about ordering dessert. Is it because I'm a woman, and it's supposed to be taboo and naughty and yogurt-commercial-ish for me to be treating myself? Is the implication that I'm sneaking something or cheating on a diet?
You may say I'm overreacting, that it's in my head like when I worry waiters think I'm my father's younger girlfriend and I call him "Dad" unnecessarily loudly in front of them. Perhaps. But I have felt the dessert girls club imposed upon me, and cringed at it, and not two nights ago while dining out with a group of female friends, a waitress leaned over the table conspiratorially and in the voice of an indulgent nanny said, "do you like chocolate and peanut butter?"
When I was a waitress myself, I am told I overcompensated. At one early gig, I had a colleague who was very nudge-nudge wink-wink about sweets, especially with tables of women, and threw around words like "sinful" a lot and as a result thereafter I not only never suggested dessert to anyone (something my various managers had to speak to me about several times) but if someone did order cake or pie I was stern and stony-faced throughout the whole transaction. (It should be said that this person also had the annoying habit of saying she'd gone to "a little school in Boston" instead of just answering "Harvard," so maybe I shouldn't have let her influence my behavior one way or the other.)
I have asked various male friends if they've experienced the phenomenon. They were 1) not interested and 2) hadn't. I choose to believe it's of a piece with the unhealthy relationship our society has cultivated between women and food, where matter-of-fact enjoyment has no place at the dining table. This is not the fault of any server - most of whom are not even guilty of conspiring - but rather of centuries of creepy marketing, a pernicious diet industry, and six seasons of Sex and the City. In answer to your question, yes, I will have that piece of pie. A la mode. And without a side of knowing winks.