Q: I have a major crush on an intern, and I’m not her supervisor. Is she fair game?

A:I know, I know. There is nothing more powerful than the allure of dating someone you can’t have, or someone who seems off-limits. So first off, ask yourself if the inaccessibility factor is the reason you’re crushing so hard. If that’s the case, then move on. Your career is not worth the price tag on this fun flirtation. But if you suspect you’re developing real feelings for this girl? Approach the situation with caution. Take the scenic route to her affections—not the expressway. Here’s what to do:

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  • Think on it. Lovesickness can cloud your mental clarity, so let me lay it out for you: If she’s an intern, she’s probably pretTy Young, and a free-spirited college student may not be on the same relationship page as you. So consider whether or not the age difference will bother you. You’ll also want to think about what can happen if you have a bad first date or she doesn’t return your affections. “What if it ends horribly or awkwardly somehow? Do you want to spend the next three to six months seeing this intern every day?” says dating expert Neely Steinberg. “Will it affect your reputation at work, especially if it's a small company where gossip tends to travel far and fast?” Ask yourself if she’s worth the risk.
  • Look into company policy. This is a must. Whether it’s recorded in black and white somewhere, or there’s an unspoken code, you have to find out if you’re allowed to date any intern—whether you’re her superior or not. “My guess is that there is some sort of employee handbook that addresses these issues,” says Steinberg. “If there isn't a defined policy, there may be an unwritten rule within the office culture. Try asking someone who has been at the company for a while for advice.” Choose someone you trust—you definitely don’t want rumors circulating about how you eye the underlings.
  • Be patient. Perhaps the best advice, though, is to keep it platonic at first—especially if she lives nearby and the internship is set to last only a few months. Become her friend. Get to know some basics about her. Advise her in professional ways. Be that super-nice, upbeat guy who’s always happy to help—and is super-attractive, too. “This way you are laying the groundwork for something romantic after she leaves, when there's a lot less on the line,” says Steinberg. Stay on her radar, while keeping a safe distance—and then, when her last day finally arrives, you can go ahead and make your move.

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ABOUT THE HOT GIRL: Claire Austen is a 20-something freelance writer, sports enthusiast, and polka-dot-lovin’ everygirl trying to bridge the gap between what men know about women and what women wish men knew. She gives smart, super-honest advice about your biggest dating and relationship conundrums.