Heigl may be too career savvy for her own good. Oh, sure, the decision to team with director Robert Luketic and screenwriters Karen McCullah Lutz and Kirsten Smith on the romantic comedy The Ugly Truth is a sound one on the surface. The last time those three got together, their Legally Blonde launched Reese Witherspoon to (short-lived) "New Julia" superstardom. If you were Katherine Heigl*, would you turn down a project with such that kind of pedigree?

The answer, of course, is no. But here’s the problem: Legally Blonde should’ve been bigger. Though Lutz and Smith are as good as it gets when it comes to the bubbly, teen-skewing chick comedy (they also did the highly tolerable 10 Things I Hate About You and She’s the Man), Luketic’s flat, uninspired direction probably shaved a good $30 million off the final domestic take, if not more. True, the $95 million gross indicates that the movie obviously worked on some level, but the screenplay is too polished for the film to merely be a sum-of-its-parts affair. I honestly believe that, in the hands of a skilled comedic director, there was something great and (potentially) enduring to be crafted from that premise. It’s a bigger missed opportunity than you might think.

There’s a reason why Luketic’s subsequent features, Win a Date with Tad Hamilton and Monster-in-Law, qualified as two of the worst movies of their respective years – and I don’t think it’s all about the writing. The guy just isn’t adept at comedy, even though the box office for Legally Blonde and Monster-in-Law suggest otherwise. And while I understand that you can’t work with Judd Apatow every time out, there has to be someone better than Luketic (which reminds me: what the hell happened to Amy Heckerling?).

Then again, you’re a woman. You’re pretty much screwed for options, even at twenty-nine. Shit, work with Luketic every year until you’re thirty-five, ‘cuz that’s when the roles disappear.

*There are a lot of Prince songs that aptly describe my feelings for you. And, more to the point, what I’d like to do to you.