Miss Information

Should I ask out the one woman in my three-person screenwriting group?

By Cait Robinson

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Dear Miss Information,

I'm a screenwriter who meets with two fellow screenwriters every week to workshop our material. We've been doing this for about six months, with a few breaks in between. The dynamic is interesting, as I used to be a graduate teaching assistant for the other two writers; they were my undergrad students. They've both cited me as an inspiration to continue down the road towards screenwriting after college.

One of the former students is a hilarious, really talented, really intelligent young woman who I've always found attractive but never flirted with because I care about academic ethics. Now that we're all living in Hollywood and are film-industry equals, there's no formal ethical barrier to me "making a move." Still, I very much hesitate. I have difficulty not feeling like an authority figure towards her, exacerbated by a ten-year age difference. We're also quickly becoming friends, which is often a problem in dating situations. We both get a lot from this workshop, and I fear that an attempt to ask her out might make the group feel awkward. (I completely admit to fearing rejection, but I'm more worried about the workshop fallout than the personal fallout.)

The pragmatist in me sees our creative professional relationship and burgeoning friendship as beneficial to our careers and personal lives. The romantic in me sees a beautiful, funny, insightful young artist who responds to me with warmth and admiration. Do I make my attraction known and risk breaking up the workshop, or quietly admire her as we become friends and future WGA Awards contenders?

— Don't Stand So Close

Dear Don't Stand So Close,

Remember when Kathryn Bigelow won the Oscar for The Hurt Locker, and every single camera in the room zoomed to James Cameron's face, expecting him to rend his garments or shake his fist at an unfair god? Well, the joke was on them, because nothing happened and the ceremony stayed boring.

Cameron and Bigelow are an extreme example. Let's hope your screenwriting and dating careers take you both to a room where you have to painfully pretend you aren't exes! That's a fairly decent problem to have; at least then you can cry into your millions. For now, though, I think you're making a bit much of this writing workshop. It's casual and it's three people. If it implodes, there won't be much fallout. You live in L.A. Throw two stones and bam, two new workshop partners. Ultimately, it's easier to worry about "the group" than it is to face the possibility of rejection.

Of course, the ten-year age gap and difference in life station might pose more of a problem. These are not insurmountable odds, just something to be aware of. Is she dating you, or is she dating Robin Williams in Dead Poets Society? There is, unfortunately, no easy test, but you seem pretty tuned-in. I think you'll be able to figure it out.

If you really want to navigate the fuzzy line between "friendship" and "dating," you'll need to have the same contingency plans one normally does. Can you keep an impassive face while the cameras zoom in? If things go south, can you return to some semblance of normalcy without making it awkward? Take a deep breath and ask her out. This situation is only as high-risk as you make it.