Ask Away: Should You Ever Date a Coworker?

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KissWelcome to Ask Away,’s new weekly column! Every Monday, we’ll pose an employment-related question to a group of experts and share their answers. Have a question you’d like to ask the expertsLeave it in the comments, and you might just see it in next week’s Ask Away!

This Week’s Question: Is it ever okay to date a coworker?

“About 14 years ago, I met my wife at work. We were dating secretly at first because we didn’t want to cause any concern. However, we didn’t work in the same department, and I feel that did play a part in making it a success. People are people, and when they spend a lot of time together, the level of attraction will change naturally. I felt lucky to have had the chance to know my wife as a friend first. There aren’t many couples who can say the

“From a business prospective, I am a small business owner now, and I can understand the risks. But if we don’t let others be human at work, my guess is that they will find somewhere else to earn a living. Even if coworkers don’t date, they are all interacting while on the job. This in itself is like dating.”

-Christian Sees
Integrus Financial, LLC

“I met my wife at the office, so you can guess which side I’m on when it comes to workplace relationships. But since I’ve been through it before, I also know the challenges and pitfalls of dating a coworker. You have to deal with gossip and perceived favoritism, and if the relationship doesn’t work out it can be pretty awkward. The key is to remain professional and transparent whenever you’re at work.”

-Mike Collins
Personal Finance Blogger

“This is a little like asking [if it is] ever appropriate to date a classmate. The only difference is that people in the working world are more jealous, bitter, gossipy, [and] mean, and less mature than people in school are — or at least when it comes to relationships it seems they are.”

Steve Silberberg
Owner and Founder

“We spend [so much time] at the office. It is only natural to become attracted to someone you work with. If your office has a strict ‘no dat[ing]’ policy, stay away. If it doesn’t, go for it, but tread with caution. No PDA at the water cooler or at any company events — including the holiday party. Don’t try [to] hide it, because your other coworkers will realize it the second after you have your first kiss. Office environments are similar to a high school — try not [to give into] that dynamic. Don’t let the gossip spread and take over.

“If you are [at] different seniority levels, think about asking to transfer departments if the relationship gets serious you do not want to be accused of favoritism. If you are uncertain, head to HR: that is what they are there for.”

Jill Jacinto
Associate Director, Editorial and Communications
WORKS by Nicole Williams

“1. Check the office policy — it is important to be aware of your company’s regulations and take them seriously if you value your job.

“2. Keep your feelings out of the office — people may not say it, but it lacks professionalism to behave like a couple rather than colleagues in front of coworkers or clients. Public affection should be limited to private
time, not company time.

“3. Ask yourself some hard questions: How will you handle the ending? Even before the romance has begun, ask yourself what the risks and possibilities [are]. Is it worth potential drama? Will it affect your chance for advancement? Has your love interest shown they are a high risk for emotional immaturity? Do you feel confident they will handle the relationship professionally, regardless of the outcome?

“4. Dating the boss is definitely going to have an impact on your reputation. If this is a possibility, a serious conversation should be [had], and a reassignment to another department or supervisor may be your best option. If you are the boss, think like a professional and make sure to handle the situation accordingly so your new love interest — a.k.a. employee — is not set up for failure. Do this before you start a serious romance, preferably before you start dating.

“5. Keep you vacations, weekends, and personal time out of the office. Don’t discuss your plans or your upcoming adventures during the work day. Keep it professional — no winks, hugs, special signals, etc.

“6. Don’t let your boss be the last to know. If you are involved in a serious relationship with a coworker, it’s best [for the boss] to hear it from you, rather than through office chatter.

“7. Be careful what you post on social media. Nothing is private, and there are all kinds of repercussions that come can from a post that shows poor judgment.”

-Diane Gottsman
Author and Owner
The Protocol School of Texas

By Matthew Kosinski