9 Ways To Date Someone You Work With — Without Making Things Really Weird
If you want to mix business with pleasure, make sure you do these things first.
Mindful Media | Canva As many red flags as the office romance waves, it actually can make a lot of sense. Spending a good chunk of our waking hours around the same people naturally allows us to get to know them better and become more comfortable talking, joking, laughing — maybe even flirting.
But when you date someone in your office, it can become more and more difficult to leave your relationship drama at home where it belongs. Why? Because it follows you on your commute. And what if steamy encounters of undeniable chemistry tempt you out of your super-professional comfort zone … and into the HR department for a talk about the office's dating policy? Keeping work professional and keeping what's personal exciting is something most sensible women opt not to put on their to-do list. There's no denying that it can happen.
Here are 9 ways to date someone you work with — without making things really weird:
1. Your boss is off-limits
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Don't date your boss. Don't date your boss's boss. Or even their boss. Just don't! You'll end up in a sticky situation, a mess that could do more harm than good to your career and heart.
Michele Molitor, a certified coach and leadership expert, emphasizes that "firm boundaries let in what you do want — good people/opportunities/interactions" while helping "you keep out what you don't want — toxic or negative people/circumstances." Dating your boss creates a power imbalance that destroys professional boundaries entirely, making it nearly impossible to maintain objectivity.
2. Talk about it
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When you two have realized things could become (or already are!) serious, be open with each other about the range of what-ifs. I know this isn't an easy conversation (especially when you're floating on air in the honeymoon stage), but trust me — it's one you need to have.
What will you do if you break up? What will you do if someone finds out when they're not supposed to know or before you are ready to share? What will you do if your company's policy forbids inter-office relationships? As a friend's colleague, Eileen shares, "One of the first points of conversation we had was what if we broke up? How would we handle our professionalism, etc? We wanted to make sure that we remained professional and cordial."
Being on the same page about how you'll handle certain key situations — even if they don't occur — will, in the meantime, help you and the relationship feel safer, stable, and secure. More importantly, you will already have an escape plan in place should the storm of questions hit unexpectedly.
3. Find the perfect balance
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Keeping your personal life out of the office is hard enough (if not impossible), especially if you're good friends with your colleagues. When you're dating one of them? It's even harder! That's why it's crucial to set clear expectations with your significant other about your behavior at work versus your behavior at home.
My colleague Beatrix, who is still in a solid and healthy relationship with a great man she met at her previous job, admits that, a few months after becoming official. "He broke up with me! He claimed I was mean to him at work. He said if he wasn't talking to me the entire time at work and saying everything perfectly, I would get mad and make him not want to go to work anymore."
What these two needed to clear up, but hadn't even mentioned yet, was how they were going to balance their personal relationship in a professional environment, especially since they worked so closely together every single day. "I thought he was flirting with the girl sitting next to him, and it hurt my feelings," Beatrix further divulged. "Then I realized I was just being insecure." Two weeks later, after some frank discussions, they were back together. So, what does this mean to you?
Life coach Mitzi Bockmann emphasizes that "relationship boundaries and expectations can hurt your partnership if they aren't communicated clearly to each other." Bockmann warns that when boundaries and expectations "don't match," partners can end up feeling confused or hurt by behaviors that seem perfectly reasonable to the other person.
Don't let your job get in the way of your relationship, but also don't let your relationship get in the way of your job. Talk to each other, and discover what works for you in terms of balancing the two. Remember: it's probably part of your job and the other person's to communicate — perhaps frequently — with people you think are a threat. Jealousy happens, but business communication is just that — business. It almost certainly doesn't mean he likes her.
Don't talk about work after hours. Doing so will allow you to focus on your relationship when away from the office and your professional one when at the office.
4. Quiet the gossip
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Unless you are the world's best secret keeper (hopefully, you're a bit more subtle than Megan's fling, who "whispered" things to her in passing), people will probably catch on. Every office has some gossip, right?
If you want to avoid the murmurs, be upfront with your colleagues and boss. Assuming your HR department allows inter-company dating, it's better to be open about your relationship and gain support from your coworkers rather than try to hide it, which could potentially create a hostile work environment.
Ruth Schimel, PhD, a career and life management consultant, emphasizes that trust requires "being honest with yourself and transparent with others, as appropriate." While it might seem easier to keep your workplace romance under wraps, attempting to hide the relationship actually erodes the very trust you need from colleagues and supervisors.
5. Consult HR
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If you plan on letting the cat out of the bag about your relationship, be sure you're technically allowed to have one first. If your company has a policy that forbids them, you're much better off keeping things under wraps.
Patricia Bonnard, a certified leadership coach, emphasizes that "knowing what your boundaries are and how to authentically and respectfully negotiate them" is "fundamental to building a lasting relationship of any kind." Consulting HR is about gathering critical information so you can make an informed decision about how to proceed.
6. Invest in friendship first
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But what if it's too late? What if you threw caution to the wind, had a fling with a coworker, and things didn't end quite as well as you were hoping? Well, now's the perfect time to dig down and remember the advice your mom gave you: Friendship is golden. Try to keep in mind all the good things that made you notice that coworker in the first place, and focus on the positive aspects of an ongoing professional relationship.
If it's possible for you, try not to dwell on what went wrong. Mooning over a relationship gone bad is what you do at home while eating too much ice cream and watching that tearjerker for the fifteenth time, not an activity to do at your desk. Take it from Jane, who learned the hard way:
"A few months after I started working at a small internet company, I started dating a coworker. Things were going great for a few weeks — at least I thought so until he told me things weren't working out, and he wasn't interested in a long-term relationship with me. I took it pretty hard, and working together only made it worse. Seeing him every single day (boy, did I hate working in an open office then) reminded me over and over about how much I missed him and how mad I was that he wasn't interested. I eventually got over it, but it was rough."
7. Use caution tape
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Why? Because often we jump freely and willingly into a relationship without considering all the consequences. Sound familiar? I thought so. This can be especially hard if this person is a superior or someone with whom we work closely or regularly.
Mixing work and play and not keeping the separation between our individual lives and our dating lives that we're used to can pose relationship-ending dangers at the best of times. It's worse if you're interested in someone you work with daily. But even if they are in a separate department or on a different floor, making sure you're not bringing your relationship with you to work each day adds even more stress. So you have to decide. Is all the fuss and bother worth it to you?
8. Consider the excitement factor
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Of course, office relationships have a definite positive side: The excitement factor. One former colleague, Megan, describes her fling: "He'd send me long looks in the hall or comment under his breath to me in passing. Pretty soon, everybody knew something was going on, even if they weren't sure exactly what. If I could do it over again, I'd probably have asked him to tone it down a bit, even though it was exciting to be getting that kind of attention in such an illicit place. Okay, maybe it was fun how it was."
Admittedly, an office fling can spice up your life. And don't forget the mating ground that is the office party. As my friend Julie learned, "I've hooked up with a coworker after a particularly, shall I say, 'festive' office party, but nothing came of it. Until, uh, we did it again. I don't regret anything, but, to be fair, I don't remember much either." Oops.
That having been said, at a time when so many of us are holding on for dear life to the jobs we have or desperately searching for another one, it's not unlikely you're putting in a little extra time on the job, and regretting how little time you have to further develop and explore your personal life.
But what if that special someone is in the cubicle adjacent to yours? Is the person in sales you hear making calls all day? The one you run into at the instant coffee machine at least twice a day? Yeah. OK. Maybe. But more likely than not (read: there are exceptions, and I've witnessed them!), office relationships are doomed to failure.
9. Handle the inevitable
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Whether we know better and want to do it anyway, we can't deny the palpable attraction, or both, office relationships happen. There's no denying that. If you have an eye on someone, are already involved, or are debating ending an affair with a coworker that just isn't working for you, here are a few things to remember when dealing with the good, the bad, and the ugly.
Like in business, and regardless of where your love life stands, you can benefit from heeding the advice of others and learning from their successes and failures. For the right partner, you can make a work relationship work. Just make sure you're in it together. Teamwork!
As Beatrix would say, "My mom told me to 'Never date anyone at work.' I say, 'Never date anyone at work unless you are in love with them and are best friends with them first!'"
Anna Hennings is a freelance writer and former contributor for Excelle.
