Dating Expert Amy Spencer, author of Meeting Your Half-OrangeAmy Spencer is a dating expert and the author of "Meeting Your Half-Orange: An Utterly Upbeat Guide to Using Dating Optimism and Finding Your Perfect Match" (out in February 2010, Running Press). We asked her the dating questions that continue to baffle us.

Lemondrop asks: Should you date someone at work?

Amy answers: If you're on the same-ish level at work and you don't work directly next to each other, then sure. The most recent stats show that 18 percent of married couples met at work -- it's where your passions lie, where you spend most of your time. But when you start messing with title imbalances and nearer desk distance, things can get complicated.

So before you date someone at work, create the worst-case scenario -- because that's how things sometimes play out. If this is your boss or your assistant we're talking about (speaking of, how cute was "The Proposal," right? Anyway ...) determine what will happen if things go sour: Maybe you'll be worried about being promoted or promoting; maybe you'll feel awkward in meetings; maybe you'll screw up the dynamic of being able to boss around or be bossed around as part of the job.

Meetng Your Half-Orange by Amy SpencerIf he works next to you and things don't work out, maybe you'll have to hear about the new girls he's sleeping with or listen while he orders flowers for someone he likes. Perhaps your after-work drinks with the guys will become awkward.

The drama of a public office split could also affect your work or how others there view you -- how important is that to you? (My personal worst-case work scenario came true: The guy I dated in the office cheated on me with another girl and then she got a job in my office. If I could do that all over again, in other words, I wouldn't.)

If the worst case sounds ugly, do yourself the favor of seeking dates outside the office. But if you think you can deal with the worst, it's worth trying for what could be the best! Flirting by Post-It and sneaking off for secret lunches adds an element of danger to a dating situation you just can't get anywhere else.

Amy Spencer has written for Glamour, New York, Harper's Bazaar, Page Six magazine and among other publications. She is the former host of the relationship call-in radio show "Sex Files" on Sirius satellite radio's Maxim channel, and also created and writes for The Dating