You picked the right person to ask about combining work and personal interests. For 14 years I lived with my business partner, and for six more we have continued to work side-by-side without the personal aspect (see the STEP article Who Would've Thought...? for the juicy details). So my knee-jerk answer is “yes, of course it’s possible” for professional and personal interests to coexist. But while my experience with personal/professional relationships has been positive, there are so many horror stories and tales of broken promises, hearts, and contracts that it’s enough to give even the most hopeless romantic reason for pause. Let’s look at some questions you should ask yourself before heading down what can be a slippery slope.

1. Who’s on top?
Reporting relationships and hierarchy are major concerns if you are considering a relationship with a coworker. If the apple of your eye is also a subordinate, I urge you to exercise caution. Should the liaison go awry, besides discomfort and awkwardness, you could be opening yourself to litigation or sexual harassment charges. Many people faced with a strong attraction have decided to wait until they are no longer employed by the same company to begin a personal relationship. The problem with this notion, of course, is that the human heart cannot be put on pause until the timing is more convenient.

If you’re the subordinate in an at-work romance, you should consider how your liaison could affect your career path. The implications of “sleeping with the boss” can be disastrous to your reputation, relationships with peers and colleagues, and even your self-esteem. After all, who wants to ask, “Did I get that promotion because I deserved it, or … ?”

2. What’s the company policy?
In most instances, the bigger the organization, the more rigid the guidelines involving issues such as nepotism. Oddly, some companies turn their heads to dating among the ranks, only to draw the line at married couples working side by side. Other organizations, however, will terminate one or both parties for “professional misconduct.” In addition to a formal policy, most fi rms also have an informal code of conduct that will infl uence how an at-work liaison is regarded. In some cases, even if the manual says it’s OK, fallout from peers can be enough to nip a romance in the bud.

If possible, find out if there are precedents for your situation. Past is often prologue, and if other romantics have blazed a trail before you, your travels may be easier—or at least less fraught with surprise and danger.

3. How “out” will we be?
If you’re like the rest of us, you spend most of your weekday hours at work. We get to know each other pretty well in those 8–10 (or more!) hours and—let’s face it—it can be hard to hide a secret. As you enter the tunnel of love, you are well advised to consider who’s watching. How much of your personal business do you want to share with coworkers? And don’t overlook the (inevitable) lovers’ quarrel—don’t think for a moment it will go unnoticed.

4. What happens if we break up?
OK, here’s the real reason why office romance is worth writing a column about: What happens if the whole thing tanks and the two of you call it quits? Most of us have suffered a breakup and had to endure “running into” the ex because you are on the same volleyball team, or you go to the same vet, or … whatever. Imagine a world in which you not only run into the ex, but have to report to, work with, or depend on the person you used to sleep with. The productive creative state is such a fragile thing that almost anything can throw it off. You can’t just call in sick until you’re over it.

I can tell you from experience that “sex and the office” can be fun, and in my case—because we were (and still are!) business partners— even profi table. But this particular pathway is also one that is littered with pitfalls and potential trouble. You are best to mind both heart and head ... and proceed with caution.