Dear Hobie & Monk,

OK, so I actually heard a guy in his 20s call into a radio show with this question this week, and I had to pull into the parking garage at my office before I heard anyone’s response. I’ve been thinking about the situation ever since, and I couldn’t resist sharing it with Monk and our readers.

His question: My firm’s evening Christmas cocktail party is this weekend, and most people are bringing either their spouses or dates. I just met a woman on an online dating website and am planning on bringing her to the office party. Some of my friends think I have totally lost my mind since this would be our first date. What do you think?
– Ho-Ho-Hobie

Hobie: I think you have very, very smart friends. Friends who prefer that you keep your job so that you don’t end up sleeping on their couches and mooching breakfast while looking for a new one.

Look, it’s great that you’re excited about going out with this woman, but your firm Christmas party is not the appropriate setting for first-date roulette, regardless of how you initially found each other. She could be wildly inappropriate or lethally dull or perfectly splendid.

But this is your chance to enjoy and impress, without worrying about the unknown and potentially cringe-worthy, so invite someone you know well or go alone. And by the way, you don’t get to be dull or inappropriate either.

Monk: I suggest you ignore Hobie’s advice and invite “Dot Com Date Dottie.” But before you do, I suggest you check the following three boxes.

First, take a minute to consider what you think you know about your date. Does she present herself as someone who would be a good fit for an office-party situation, or would a better first date be something like a monster truck show?

Ask yourself this question and answer yourself honestly. If the answer is more office party than monster truck, check box No. 1.

Second, ask Dottie how she feels about accompanying you to your office party as a first date. Give her a little preview of what to expect. Is she all in? Check box No. 2.

Finally, devise a strategic plan that will maximize the potential for a really great “Hallmark, made-for-TV movie starring Amy Adams and Owen Wilson, first date office-party” experience. Go out for a drink with Dottie before the party.

Ask and answer yourself, “Was I overly optimistic when checking boxes No. 1 and No. 2?”

Proceed to office party with caution. Forgo the opportunity for shots with “Lampshade Larry.” Have a fabulous time. And mystery caller, if you happen to read Hobie & Monk (of course you do!), let us know how it goes.

Hobie and Monk are two Alexandria women with husbands, children, dogs, jobs, mortgages, obsessions with impractical shoes, English novels … and Ph.D.s in clinical psychology. Their advice, while fabulous, should not be construed as therapeutic within a doctor-patient context or substituted for the advice of readers’ personal advisors.