Sleeping with Your Boss? What You Need to Know Before You Make Him Your Sugar Daddy: Part 2

Sleeping with Your BossIn some cases, when cowork­ers or other supe­ri­ors sus­pect that some­thing is going on, they may report it to the Human Resources depart­ment. This is prob­a­bly one of the biggest and most impor­tant things to be aware of when your boss is also your sugar daddy. A lot of employ­ers have strict rules for­bid­ding rela­tion­ships between cowork­ers, espe­cially bosses and employ­ees. If you get caught, you may both find your­self on the receiv­ing end of dis­ci­pli­nary pro­ce­dures because of your office romance. Of course, this doesn’t really apply if your sugar daddy owns the busi­ness, but that doesn’t mean other employ­ees won’t be upset. Given the cur­rent job mar­ket, it is a good idea to check the company’s pol­icy and put the wel­fare of your career and posi­tion ahead of any feel­ings you have for one another—unless, of course, you are both sure that your feel­ings are serious.

Before you decide to go ahead and take the risk of get­ting involved with a coworker, ask your­self if it’s worth it. Are you sure that it’s more than just a crush? If you’re plan­ning on pur­su­ing the rela­tion­ship, it might be a good idea to start look­ing else­where for a job if you can. This may not work in all sit­u­a­tions and could be a lit­tle dif­fi­cult with the cur­rent job mar­ket, but it’s worth a shot given the risks of get­ting caught. If you are fired for vio­lat­ing a pol­icy, it will make it extremely hard, if not impos­si­ble, to use that employer as a ref­er­ence for another job.

If you have already taken the plunge and are involved with the boss, and if peo­ple at work don’t already know about your office romance, try to remain as dis­creet as pos­si­ble. Main­tain a pro­fes­sional atti­tude and appear­ance in the office at all times. It may be cute to kiss in the copy room, or pinch his butt by the bath­room, but it’s bet­ter to play coy. Don’t use com­pany credit cards for trips or dates, and most cer­tainly do not use your com­pany e-mail accounts to talk about your relationship—it can all be read and tracked by other superiors.

Dat­ing a boss or get­ting involved with a coworker is a big risk. If you’re will­ing to take it and you’re ready for a rela­tion­ship, then go for it. But always remem­ber, you need to be ready in case your rela­tion­ship is dis­cov­ered. As the say­ing goes, “By fail­ing to pre­pare, you are prepar­ing to fail.”