Should I Ask My Boss Out?
Dear Sherry,
I am 20 years old and single. I really like my boss. The company I work for clearly states that it is against policy to date someone who is in a higher position. I flirt constantly with "Scott," and he flirts back. I'm just not sure if he is interested. It seems like he is trying to make me jealous by talking about his girlfriend, who (according to his mother) doesn't exist. I would be willing to quit just to give the relationship a chance, but before I do that, I want to make sure he is interested. Once, when he confronted me about my interest in him, I denied it. How can I confront him now without making it an uncomfortable situation, if he's not interested? I really need some advice.
Deenie
Question:Sherry Amatenstein
Sherry is the author of The Q&A Dating Book and Love Lessons from Bad Breakups. She has taught dating seminars, appeared as an expert... Read more
Dear Deenie,
Although certain fringe feminists might find you a hopeless case -- to wit: "I would quit just to give a relationship a chance" -- I am more sanguine. You're just a victim of your youth, which causes you to be idealistic about love. You think marriage is the Holy Grail, a free lifetime pass to happiness and security. Wake up, missy, and smell the coffee: The only definites in life are death, taxes and high divorce rates.
I don't have to be part of Dionne Warwick's psychic channel to predict that if you continue chasing your boss around the water cooler and grilling his mom (FYI: Parents are usually the last to know the intimate details of their children's love lives), you soon won't have any reason to worry about your company's anti-fraternization policy.
It sounds like you're the one putting Scott in an uncomfortable position. He's not telling you he's got a girlfriend to make you jealous, but to get you off his back (and other parts) so you'll start doing some -- ahem! -- work.
It's not surprising you have a crush on your boss. Authority figures, not to mention men in uniform (even if it's the three-piece kind), are often a turn-on. But keep your mind on business from nine to five (I've got the feeling you're not the type to burn even the six o'clock oil). After hours, go out with friends to places where you might meet men.
On the off, off, off chance that Scott does have feelings for you, give him the chance to express them. But don't bet your paycheck that he will.
Sherry
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