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Workplace Dating: Will it Lead to Marriage or Unemployment?

businesswoman with hand on coworkers' chest By Andrew Strieber

Despite all the cautionary tales regarding the dangers of office romance, countless employees wind up in relationships with co-workers every year. And as you might expect when two people try to maintain both a business and emotional relationship – while spending virtually every waking hour together and keeping the whole thing a secret – workplace dating often ends in tears.

Poll just about any office, and you’re likely to hear at least one story (if not more) of workplace dating that went awry. What’s worse, the fallout from these failed office romances can be far more brutal than a run-of-the-mill relationship. At least in normal life, if you look at the person you thought you’d marry and suddenly realize that you actually can’t stand the sight of them, you can just break up. But when this person is a work colleague, you may still have to maintain a professional relationship no matter how badly things end. Depending on the circumstances, failing to do so could cost you a raise, a promotion – or even your job.

Of course, warnings about the dangers of workplace dating and office hookups are nothing new. The phrase "don’t dip your pen in the company ink" is a well-worn cliché, and some companies are so concerned about the negative effects of office romances that they expressly prohibit workplace dating. Yet, despite this, co-workers continue to wind up in bed together, restrictions and warnings be damned.

So if workplace dating is such a bad idea, why do employees keep doing it? Is it because the stress of working together creates a unique bond between people? Or that as employees work longer hours, the office has become the only available place to meet people? Maybe the truth is that in spite of conventional wisdom, not all office romances are destined for failure. People who are drawn to the same employer often have common interests and a similar outlook on life. In fact, some of today’s best-known power couples began their relationships while working together. Then again, some notable romance disasters also began with workplace dating, so it’s important know what makes office romances succeed – and what makes them fail.

If you have you got your eye on a co-worker but don’t know whether you should make a move, proceed carefully. Handle your office romance the right way and you might live happily ever after; screw it up and you could wind up looking for a new job. If you’re not sure whether to act on your office crush, try taking a queue from these famous (and infamous) couples for some of the main do’s and don’ts of dating someone in the workplace:

  • Bill and Melinda Gates

    Bill and Melinda Gates met at a press event in 1987, and married in 1994. For many years Bill continued to run Microsoft while Melinda headed the Bill & Melinda Gates Foundation, dedicated to global philanthropy. Now, after retiring from Microsoft, Bill and Melinda run the foundation jointly.

    Workplace Dating Advice:

    Give each other space when you’re in the office. Don’t crowd each other or constantly check up on each other. If you were both independently successful before you began dating, there’s no reason you can’t continue the same dynamic after getting together.

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  • Barack and Michelle Obama

    Barack and Michelle Obama met when they both worked at a Chicago law firm, and Michelle was assigned to mentor Barack while he was a summer associate. They married in 1992 and have continued to work together throughout the rise of his political career.

    Workplace Dating Advice:

    Communicate clearly about how you should act at work. Do you want to be open about your relationship, or keep a professional distance? If one partner feels like sharing with others while the other wants to pretend nothing is happening, this can quickly lead to trouble.

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  • Julie Chen and Les Moonves

    CBS “Early Show” anchor Julie Chen married network head Les Moonves in 2004, just two weeks after he obtained a divorce. Since then she gave birth to a son in 2009, and two remain together.

    Workplace Dating Advice:

    Keep your involvement private until you’ve both determined that you’re in it for the long haul. This is (of course) especially important if one or both partners in the relationship is married, but also helps avoid unnecessary questions of favoritism. Once you are sure the romance is for real, it’s time to “go public” and address any workplace concerns.

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  • David Letterman and Stephanie Birkitt

    Letterman’s affair with Birkitt while she was working as his assistant famously came to light when the comic became the subject of an attempted blackmail. Letterman addressed the relationship and blackmail directly on his show, although the affair prompted questions from some pundits about the work environment on his show.

    Workplace Dating Advice:

    If you are in a boss-subordinate relationship, considering transferring out of the same department so you’re not both put in a potentially risky situation. When bosses and their employees are found to be dating, this raises questions of impartiality and can attract the attention of top management, who worry about potential legal landmines.

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  • Ben Affleck and Jennifer Lopez

    Lopez and Affleck’s romance caused such a media frenzy that the couple was referred to as “Bennifer,” and virtually every aspect of their relationship became the subject of intense scrutiny. Having met on the set of the movie Gigli, the film’s failure served as the culmination of the couple’s overexposure, and the two split in 2004.

    Workplace Dating Advice:

    Hollywood stars may be the only ones who need fear media overexposure, but you should watch out for “overexposure” of your workplace romance, too. If you date a coworker publicly, try not to get so involved in each other while at work that it begins to breed resentment among your colleagues. When it comes to workplace dating, a little attention from your coworkers goes a long way.

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  • Jennifer Aniston and Vince Vaughn

    Another Hollywood pairing, Vaughn and Anniston began their relationship during the filming of The Break Up. While the romance sparked plenty of tabloid coverage, it never caused quite the media frenzy of Affleck and Lopez, and the relationship appeared to peter out by 2006.

    Workplace Dating Advice:

    Your relationship should be a collaborative effort. If one of your is putting more time into the romance than the other, it could be a warning sign that you’re headed for trouble.

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Andrew Strieber is the Producer of and

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