Tuesday, December 29, 2015 Gabby Bill 1 Comments

Dating in the workplace is perhaps one of the trickiest subjects of all, because you're taking two of (arguably) the most important aspects of a person's life and making big decisions about whether or not they should intersect.

It's no surprise when I say that as an adult it can be harder and harder to meet other single people, so if you declare that you're never going to date someone you work with, you could potentially be closing yourself off to one of the few remaining avenues in which you're spending significant time with others of similar age, intelligence and income. Although these aren't necessarily important qualifications for everyone, for many there's an increased likelihood of success if the person they're interested is on a similar socioeconomic level.

Yet dating in the workplace can be dangerous, because it adds a highly emotional component to a space that, for many people, often requires a sort of cool, calm, logic-driven demeanor. I know my last company was very forthcoming in encouraging that I bring my "whole self" to work, but I still don't think they'd be thrilled if I couldn't get through a presentation because I was sobbing over my ex who was sitting at the other end of the boardroom.

I speak from personal experience when I say that dating someone at work is something I'd approach with increased caution, should I ever return to a more traditional 9-5, because I tried it twice and it ended badly both times. The first time I gave it a shot, I was a naive 22-year-old who had just started at Disney, and as the fairy tales go, an incredibly handsome Rico Suave type joined the team, and I fell victim to his charm. We didn't date for long -- 6 weeks, I think -- but a few things happened in that ever brief period of time.

1) Everyone in the office found out. It just so happened that this man's brother also worked in our office, so he knew, and with all the "water breaks" that the man himself took at my desk, it became sort of obvious that there was some level of beyond-work friendliness happening between us. I remember him actually being scolded once for distracting me too much, and there was one day that all I thought about for a good four hours was how I could lure him into the supply closet for a make-out session (it never happened, much to my dismay). There's no doubt I was distracted by his presence, and I'm sure it affected my work product to some degree.

2) It created awkwardness with my male boss. My boss clearly fell into the category of "everyone" that knew we were dating, and for some reason I think he felt it appropriate to try and "protect" me from this guy, whom he deemed not good enough for me. I remember him warning me not to get in too deep with him, and I had even heard through the grapevine that my boss had pressed the man's brother for details about how intimate our relationship had become. I realized then, just as much as now, that this conversation was entirely inappropriate, as my love life shouldn't have been a topic my boss broached in the first place, but I didn't act on it because I was stupid and somehow felt that by dating a co-worker I was asking for these things to happen. (Learn from my mistake on this one, and if ANYONE at the office ever engages in conversations that cross the line, please confide in someone and ensure that it stops. Something like this very easily could have turned into a sexual harassment issue.)

The second time I tried dating someone at work was again at Disney, but this time I was much older and, as I thought, wiser, so I assumed I'd have a better handle on making the relationship work. In some ways, I did. We did a much better job of letting only select people know that we were dating, and because we didn't work on the exact same floor or in the exact same building, we were able to keep our "water breaks" more hidden via instant messenger. The news of our dating thankfully did NOT spread like wildfire, and yet we felt comfortable holding hands or showing minor displays of affection in the presence of a core group of friends that knew we were together.

Where this one went wrong was in the break-up. I broke up with this man (and for a stupid reason, now that I have the blessing of hindsight), and things spiraled into an incredibly awkward mess. In the interim of our courtship, I had been transferred to the same building and floor, and the bathrooms so inconveniently were situated in between our desks. It became a sort of cat and mouse game where you had to pray that the other person wasn't walking to the bathroom at the exact same time, because when you did run into each other it wasn't pleasant. This ex of mine didn't take the break-up very well (and again, I understand why, and if I could apologize to him, I would), so when he saw me, he'd do a complete 180 and hurriedly rush in the opposite direction. It made coming to work sort of emotionally awful for both of us, because we'd keep running into each other and re-opening a painful wound.

Here's the thing, though. Just because it didn't work out for me doesn't mean it doesn't work out for others. One of my closest colleagues in my last role at Disney started dating a man on our team and managed to keep it super secretive for a really, really long time. Turns out they were a match made in heaven, got married and it was never an issue. Another woman on that same team is married to a high-up VP that leads another part of the marketing organization. In her case she has to make sure that she never directly reports up through her wife to avoid conflicts of interest, but the two of them have managed to stay happily married in spite of being near-colleagues.

At the end of the day, as I say with almost everything, you have to consider the course of action that's right for you. If you feel like you and your partner are really mature and could handle working side-by-side even if you break-up, then perhaps your risk of discomfort or embarrassment is lower. If you've been friends for a while, know each other well and are looking to take things to the next step, even better.

My only recommendation is that you have some frank discussions with your partner up front and come to decisions together about how you want to handle any issues that may arise. Do you want to conceal your relationship and for how long? When is it OK to discuss it in front of co-workers and how will you respond if you're directly asked about your relationship? How do you guys want to approach the workday in terms of your interactions, any displays of affection or increased time together (like during breaks or lunches)? The more you can have this conversation up front, the more you'll be prepared to handle whatever may come on the back-end.

Your turn! What is your stance on dating someone that you work with? If you've done it, how did it go?

Gabrielle "Gabby" Bill is a career coach and consultant who believes everyone should be working in a job that leaves them feeling fulfilled. She coaches groups and individuals through a reflection process, uncovering often hidden motivations, values, goals and skills as they relate to their career. These reflections are then parlayed into concrete action plans to guide clients through the process of finding, creating and landing their dream jobs. You can learn more about her services by visiting

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