Miss Information: What to do when your boss won’t take no for an answer.

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Miss Information

Have a question? Email Letters may be edited for length, content and clarity.

Miss Information is off this week. She’ll be back next week with an all-new column. In the meantime, enjoy this workplace-themed Labor Day “Best Of” and check out her other column, Awesome Advice, Way to Go!

Dear Miss Information,

After months of searching, I recently landed a nice job at a small company. I went out for drinks with one of the partners, a man I hoped would become a mentor. We were chatting about work and familyhe is divorced and has kids my age when suddenly his pursed lips were coming at me! I panicked, threw up my hands and yelped, then told him that getting involved with people at work is a bad idea. He ignored me, rambling about how he was attracted to me and how we could run away together. I said we were probably drunk after five beers each, and tomorrow we could act like nothing had happened. But the next day, he kept talking about how much fun he had, and how he’d like to go out again. I am friendly, but dress conservatively and have been very careful to not give out mixed messages. I planned on working here for at least a year, and enjoy what I do. My guess is that he sees me as easily replaceable. Either that, or he’s crazy. What do I do? — Anti-Office-Ho-Bag

Dear Anti-Office-Ho-Bag,

Crazy? More like predictable and horny. I understand the office is small and you’re just trying to make friends, but remember that you are brand-new. Fresh meat. Young and, I’m guessing, attractive. No one’s sick of your face yet. Once a few months roll by and they see you on laundry day, watch you snack on mustard packets and hear you on the phone, fighting with customer service over a refill for your psoriasis condition, you’ll be seen as less of a sexpot and more of a real person.

There’s also the small-office equation. Limited choice theory. The more taboo the situation and the fewer the people, the more likely someone is to develop an attraction. It’s a small office, he’s older than you and in position of authority; you’re the Megan Fox of the spreadsheets.

Don’t go out with him again, except in a group setting. Be friendly, but busy. Have a multitude of all-purpose excuses handy, and throw a pic of a cute boyfriend-looking guy on your desk or screensaver. You might want to also look into your drinking. Five beers and you’re still guessing if you’re drunk? High tolerance or no, that’s quite a few for platonic after-work beers. Dial it back a bit and save the boozing for your real friends and less volatile situations. Who wants to waste a drunken good time worrying about doing something that will endanger your job?

Dear Miss Information,

I met a guy on the personals and we started talking on the phone. It’s become serious. Daily phone calls, emails, and instant messages. The problem is he doesn’t know my real identity. I posted some pictures of my coworker instead of me as a joke in the photo section. The coworker and I aren’t even friends! In fact, I kind of dislike her! Physically, I’m not ugly, but we don’t look alike. (My guy friends have seen both our pictures and have said that it should be no problem because I’m more, not less, attractive than the woman in question.) I know I should tell him the truth but I don’t know where to start. — Image Problem

Dear Image Problem,

A joke? What the fuck kind of joke is that? A rabbi, a priest, and a wackjob with boundary issues walk into a bar on the Internet. . .

The only thing you can do now is find the hottest, best picture you can of yourself and send it over in an email begging for understanding. Showing up at his house looking like a completely different person without some sort of warning is ill-advised and unfair.

Make sure your email, one, recognizes the craziness of your behavior and the fact that he might have major doubts about meeting you (“I’m sure you’re probably don’t want anything to do with me, but I would love to meet you for coffee or a quick drink and show you I’m actually a very nice person,” and two, attempts to explain your joke in a manner that’s neither too cavalier (“Ha! Ha! Aren’t I a stitch!”) nor too serious (“Being told I was too ugly to play toxic waste in the Earth Day pageant was really the beginning of my issues regarding my looks. . .”)

Do yourself a favor and take what you did seriously. It was not a joke, but rather a deliberate deception. Don’t minimize it. I can only tell you how to stop the bleeding and possibly still get a date out of this guy. It’ll take some long talks with a friend or shrink to help you better understand why you did what you did.

Dear Miss Information,

It’s an old story: I’ve fallen for a coworker. Over the past few months we’ve engaged in a couple of after-work make-out sessions, but she insists there can be nothing more because we work together. I’d accept this, but I just can’t seem to — I really do think I’m in love. My question: is it possible to respectfully pursue her? Or is any pursuit a sign that I don’t really respect her and that I’m just a selfish prick? (Oh, and if you could offer any tips on how I might pursue her, that’d be great.) — Besotted in Berkeley

Dear Besotted,

If you put funny Post-Its in her cubicle and deliver her favorite candy bar via inter-office mail, then no, you’re not a prick. If you barrage her with emails, visits to her cube and subtle threats about telling the boss if she won’t join you for an evening of French cinema, you’re still not a prick. You’re a white-collar stalker.

Office romances make people paranoid, and this paranoia causes them to apply a higher standard to prospective partners. There’s “Hot,” and then there’s “Hot, but do I really want to take the risk?” Ninety-nine percent of folks are probably going to fall into the latter category. Including you. We also don’t know if she’s using the coworker thing as an excuse because she’s not that into you, or if it’s a genuine showstopper. For all intents and purposes, we’re dealing with a long shot. Forgive me if this sounds calculated and grody, but you need to court this woman like you would a client. Conduct yourself with patience and class and go for the long, slow sell. Easy on the gold jewelry and aftershave, Besotted. When you go out for a drink after work (i.e., schmoozing with the client), see if you can get her to reveal the reasons why she wouldn’t be into dating a guy from work. It’s too obvious if you ask her outright, but more general questions, like, “Who was your first workplace crush? Mine was the girl at the pizza shop, blah blah…” and “What was your best/worst breakup?” will open the doors to her fears and reservations.

Then you use that information to inform your behavior (listen to me, all businessy and shit). If she’s freaked by guys who are clingy, take your time returning those emails and calls. If she had an ex screw her over by spreading rumors, show her how good you are at keeping secrets, even if it’s something stupid like stealing pens, or spilling by the coffee machine and not cleaning it up.

Barring that, the best thing you can do is just lay low, be the best possible version of yourself and continue to explore other romance options. This is a long shot, and your dick deserves a better shot than one ticket in a lotto.