Dating at Work: Perils & Opportunities

Here’s a great letter from a reader about a budding romance at work — a very common situation:

I’m a huge fan of the Tao of Dating, (which I’ve read 2x now), and we’ve spoken a couple of times online. I’m writing to you because I’m in a situation that’s mostly great, though a little tricky to navigate; and I’d love to get your take on the matter.

I started at a new full-time job about 6 weeks ago. I’ve met a woman with whom I really get along. We chat online almost all day while at work. I get along with her two female office friends. We all often go to lunch together. She and I make plans during the day to take coffee breaks together. Today we had an office beach party, and she and I ended up spending a lot of the day together. We get along great and gravitate towards one another.

If we didn’t work together, it would almost be a no-brainer. Thing is, we do, and it’s a new job. We made tentative plans to see a movie together next week. I just don’t want to rush anything or force anything. I’m trying not to invest too much into just her, but I find myself thinking about her often. I’m not afraid of being bold…I just feel like timing might be everything in this situation…(?) Any words of wisdom? It would be most appreciated.

I continue to love your work, and I sincerely hope all is well with you.

All the best,

My good man Gabe.  Nice to hear from you.  Appreciate the praise.  No need to stop, really — keep it coming :)

Awright, so this romance at work thing may seem like a sticky situation.  You meet someone you like, and you seem to get along.  But then, there are the observing eyes of your co-workers, not to mention their ever-wagging tongues — the implication, the innuendo, the gossip.

There’s also a problem of hierarchy, since one person tends to be on top of the other one, so to speak.  To compound the complications, there’s always the concern about what happens should you break up.  Then you’re stuck in the same office having to see each other every day — the very definition of awkward.

Now let’s take the flip side of this.  I want you to think about an ideal place to meet a future mate.  In the Tao of Dating books (for men and women), I talk about the three Cs that make for an optimal venue: conversation-friendliness, community and continuity.

Conversation-friendliness is exactly what it sounds like: it means that you can carry on a meaningful conversation relatively free of distraction and interruption.  A bar or club is the antithesis of a conversation-friendly venue; a dinner party the apotheosis.  A workplace, with its myriad occasions for casual conversation — lunch and coffee breaks, for example — gets high scores in this domain.

Community means that there’s a reason for you to be in a venue: you have something in common.  Two people in the same workplace already have scads in common.  Another good start.

But the real clincher is continuity — the opportunity to extend the interaction over time, perhaps over multiple encounters.  This may be the most important of the three, because people tend to make new friends over multiple points of contact, over several casual, nonthreatening interactions.  For example, a dinner party is great for having an initial extended interaction with someone new.  But then it’s over.  A night school class is even better, since you get to get to see one another once or twice a week over several weeks.  This is the structure for building familiarity and affection, and the workplace has plenty of it.

So according to the three Cs, the workplace is an excellent place to get to know a future mate.  Some caveats:

  • A relationship between a superior and a subordinate, although as old as the hills, complicates matters somewhat, since at home you’re equals but at work you’re clearly not.
  • If you work closely together — say, same department or team — that also complicates matters.  Being together all the time at work and away from work introduces new variables to deal with.  Being in the same company but in different domains tends to be easier.
  • If there is a breakup (and there usually is), you’ll still be seeing each other daily and expected to be civil around one another.

So, to get back to Gabe’s question, my advice is simple: stop overthinking it.  If you enjoy her company, hang out with her.  See what happens on a day-to-day basis.  Work is one of the best places to meet people.  where else can you get to know what people are really like, in a casual, non-threatening setting where you see one another regularly?

Don’t worry if it doesn’t work out — chances are very good you’re not going to marry each other anyway, and nothing was meant to last forever.  You’re both respectful adults and can handle whatever comes your way, so focus on the present fun instead of the future end.  If you treat each other well, even if things don’t work out, you’ll still be friends and happy to see one another.
One day at a time

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