Barack Obama got away with it. You can't.

Dear Job Goddess,

I am a summer associate at a large Chicago firm. My mentor, a permanent associate, is a serious hottie. I’ve been asking her out for the last month and a half. She consistently turns me down, telling me she doesn’t think it’s a good idea for co-workers to date. It only makes me want her all the more, so I keep on asking.
It dawns on me, however, that this might not be the smartest strategy work-wise. Do you think I’m endangering my offer?

B.O.,Chicago

Dear Readers,

The Job Goddess must come clean. Although she receives thousands of questions from law students and new lawyers, she made this one up. It does, however, accurately reflect the circumstances of Barack Obama circa 1989, at that time a summer associate at Sidley & Austin in Chicago, one of the country’s premier law firms (and featured – shameless commercial plug – in the Job Goddess’s book “America’s Greatest Places To Work With A Law Degree).
The mentor in question was a long, cool drink of water named Michelle Robinson. After two months of politely fending off Obama’s requests for a date, he convinced her to come and hear him speak to a community group. (Say what you will of Obama, he knows how to play to his strengths.) Foreshadowing what happened almost two decades later in Iowa and then nationwide, she fell in love with him and is now, of course, Mrs. Obama.
But the Job Goddess gets ahead of herself. Back at the firm, as a summer clerk, asking out one’s mentor “Is an endeavor frought with peril,” according to Susan Gainen of the University of Minnesota School of Law. Wendy Werner of Career Consultants Werner & Associates in St. Louis adds, “Breaking rank is never a good idea. In general, any time a subordinate starts having a romance with a superior, if something goes wrong, the subordinate will have to go.”
Many other current and former law firm attorney recruiting personnel were even more blunt:

“B-a-a-ad idea.”
“Are you kidding me?”
“An immediate ticket to ‘no offer.’”
“An unbelievable lapse in judgment.”

The Job Goddess must point out that the central problem here is the flirtation outside of one’s pay grade. As SuSaNi Harris Clayton of the University of Colorado School of Law and a former attorney recruiting director at a large firm points out, “Presumably at some point one of you would be voting on whether or not to admit the other to the partnership. A romantic relationship between the two of you would be inappropriate.”
Between willing summer clerks (or junior associates), the issue is somewhat different. As one attorney recruiter comments, “We look the other way with summer clerk flings. It’s viewed as being kind of cute.” Other than the risk of things not working out and your inamorato/a turning into a bunny-boiler, what could make work more fun than the promise of a little game of slap and tickle at the copy machine?
On top of that, the Job Goddess believes that when it comes to les affaires du coeur it pays to step back and look at la grande image, which completes the Job Goddess’s remembrance of high school French. Namely: If as a summer clerk you meet what promises to be the love of your life, whether it’s the supply clerk or the managing partner, the Job Goddess urges you to follow your heart. If you possibly can, heed Wendy Werner’s advice and “Cool your heels until the summer is over. It’s only a handful of weeks, after all.”
If you, on the other hand, can wait, you or your sweetie will nonetheless ultimately have to find a job elsewhere. But a job is only a job, whereas the love of your life? You’re only likely to have a half dozen of those.
And then there’s Barack Obama. While he could have waited until the summer was over to utter his romantic plea to Michelle, subsequent history has borne out his tendency not to let moss grow under his feet. Even at the time he was exceptional. Every expert the Job Goddess approached had the same reaction: “He could have done anything he wanted.” Not just a Harvard law student but an impending Harvard Law Review member, he could well have been the most coveted summer clerk in the United States of America. To borrow a line from To Kill A Mockingbird, he could have poured syrup on the table cloth and eaten it, and still received a permanent offer.
Incidentally, hitting on his summer mentor didn’t impact Obama’s marketability. Legend has it that he graduated from Harvard with 647 job offers. So things worked out pretty well for him in spite of putting the moves on his summer mentor.
In fact, by the time you read this, he may have received the greatest job offer of them all…