Double dating with the boss?

On the Job

What would you do if your boss asked you on a double date?

It sounds a little weird and awkward, but that scenario happened to a friend recently.

The supervisor asked my friend if she and her significant other would go on a double date with the boss and her mate. My friend was so taken aback by her manager's request that she blurted out, "Yeah, OK," and quickly changed the subject. She's hoping her boss doesn't bring it up again.

In our increasingly casual workplaces, how close is too close when it comes to relationships with our bosses?

It's one thing when a boss treats his or her subordinates to, say, lunch for a job well done. On the other hand, is it that strange that a manager would make a double-date request, considering we spend more time with our colleagues than with our friends and family?

Linda Barkdoll, coordinator of the human resources development graduate program at McDaniel College, says it's an uncomfortable situation all around when you cross the line into the social sphere. Her advice: Keep your personal and professional lives separate.

"From a supervisor's perspective, it's dangerous to establish a social relationship with someone who reports to you because you have to supervise them and evaluate them," she says. "Your personal relationship with them outside the workplace, that personal relationship could make [supervising] a difficult job when there are problems in the professional performance area."

For workers, social outings with the manager may elicit watercooler talk among colleagues or even worse -- like a wrong reputation as the boss' pet. And imagine how awkward things would be between you and the boss if something went awry on the date, Barkdoll says.

If you find yourself in a similar situation, what should you say? Your response may depend on your relationship with the boss, Barkdoll says.

But if you're lost for words, here are some suggestions from Kate Zabriskie, a workplace consultant based in Port Tobacco in Charles County:

  • Blame approach: "As much as I would love to do something with you, my boyfriend [or fill in the blank] finds it a little strange."
  • Direct approach: "You know when I'm away from the office, I really like to be away from the office. I rarely see anyone who has anything to do with work." Or "I'm really not comfortable bringing [fill in the name of the boyfriend] to work functions." If you do accept a social invitation from the boss, Zabriskie says you should try to pick an event that has beginning and end times. And be on your best behavior; after all, he or she is still your boss. What would you do in a similar situation? Send your stories, tips and questions to Please include your first name and your city. Subscribe to Hanah Cho's podcast
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