Is My Coworker Crush Playing Me?

Dear E. Jean: There’s this gorgeous guy at the office with whom I’ve hooked up several times. I care deeply about him, but when I try to kiss him, he’ll say: “I’ll make you a deal. You give me oral sex, and I’ll kiss you.” I want my hand held! I want to be cuddled! I want to introduce him to my friends! But he has refused over and over again on all three counts.

Last Thursday he spent a drunk night with my close friend and coworker, and they fooled around. But I feel if I just wait it out he’ll be ready to be in a relationship with me. I’m afraid that if I tell him, “No, I won’t get on my knees,” he’ll find another girl to be with. Am I being dumb? I’m serious about my career, and I’m rising fast in our company. I just want you to tell me I’m not being stupid because I feel one day this will work.—Caught in a Cycle

Miss Caught: Oh, honey, is this your first bastard? And your first big job? You sound so hopeful! So trusting! Then best you hear this from Auntie Eeee before your heart is stomped: The man is playing you for a fool. The more passionately you beg the dickering little vermin for a “kiss,” the more he’ll snigger about you to people in the office. I’m sorry, I know I’m bruising you—God knows I’ve made an idiot of myself over a jerkweed or two—but if you continue the affair, your career at that company is over.

And not because you’re having sex with the guy. (A strong, clever woman may enjoy as many men as she pleases, from the executive suite to the mail room, and still rise to the top if she’s skillful and discreet.) No, your career will be in ruins because you made a bad deal for oral sex, and making a bad deal for anything shows you to be a bad businesswoman. Your reputation will never survive it.

You may be able to gain back your rising-star status if you throw yourself into the breach, concentrate on your work, and focus on creating five or six new ways to increase the company’s bottom line. And the guy? Shut that creep down cold. Good luck.

This letter is from the Ask E. Jean Archive, 1993-2017. Send questions to E. Jean at [email protected].