Sex & Relationships

Will Dating My Coworker Ruin My Life?

Our wicked-smart sex and relationships columnist, Kate Carraway, to the rescue!

Tom falls for co-worker Summer in (500) Days of Summer

Tom (Joseph Gordon-Levitt) falls for co-worker Summer (Zooey Deschanel)  in (500) Days of Summer (albeit in a less stressful work environment than our reader)

By all rights, I should be going out with this guy I work with, but it’s complicated by spending much of our time together doing fairly intense collaborative work—we do the same job—much of it psychologically draining for both of us. Acting on the feelings could blow up both a great job and what is an existing, fulfilling relationship; just not the one I ideally want with him. —Deanna

Remember Speed? It’s amazing. Sandra Bullock’s outfit is so cute, very much what we were aiming for during peak ’90s  revival. There is a line in that movie that I think about whenever I am in a potentially scary situation with an attractive stranger nearby—and the potentially scary situation is always rush-hour public transportation, so maybe it’s also “whenever I’m thinking of the movie Speed”—which is “Relationships that start under intense circumstances, they never last.”

I don’t know the specifics of your job, but I do know that working even sort-of closely with someone in an even sort-of intense job, especially in the kind of job that is difficult or impossible or pointless to talk about with people outside of the fire-circle (I mean, do any of my non-writer pals want to know about the emotional politics of “track changes” in Word documents? Nope), especially if you get drunk or silly with work-peeps on the reg, can make for the kind of unavoidable super-bond that explains why all the foxy-fine doctors and firefighters and lawyers on TV hook up with each other. (When my advice involves both ’90s movies and network television, it is officially winter.)

When you remove the stress-y strictures of your work, when it’s just him as a guy and you as a girl, and you’re not talking about work-stress-work stuff, is it still great? When you’re doing something usually boring and tedious and unrewarding together—errands, getting bad coffee, long drives—is it still great? (I think that last bit is, most often, how you “know.”) It half doesn’t matter, though, because you could be coasting on the vibe-momentum you’ve already built up. Instead, I would ask you to take the following “pop quiz, hotshot” (Speed!) before getting too into to the idea of your work bud becoming your boyfriend: Have you seen the inside of his apartment more than once? Have you seen his not-at-work clothes, his shoes especially? Have you met his friends, and do you like and respect them at least an average amount? If yes/yes/yes, you pass.

I’ll put aside the thing of how there are likely rules, either made explicit in your employee handbook, or made implicit by the hot-goss habits of your other colleagues, about dating the people you work with; maybe what you mean by “blow up” is something else entirely, like, worst-case you’d get fired? (Would he, too? I need to know more.) Or, the combo of a heavy-tokes job plus a new romance—which, as we all know, overstuffs your skull with some substance that’s texturally between cotton candy and yarn, and makes all your thoughts and feelings coalesce as animated hearts and flowers—would blow up your job performance? Probs some combo, but, I’ll leave that with you.

A lot of people meet their person at work—proximity; common interests—so it’s not like you’re a romantic marauder or whatever to fall for a guy who is by your side doing heroic shit (are you nurses? I wish I was a nurse) all day, every day. You need to find out if you really do have to continue working so closely together—can you keep your job and still date him that way? If not, you have to decide if an untested relationship is worth one of you leaving, or if some job is worth giving up on possible, amazing love. And since “work and love” are the only things that reeeeally matter in life, that’s going to be, to invoke my fave winter-time phrase, some tough sledding.

But, on the friendship-blow-up piece, let’s acknowledge the universal truth that nobody actually cares about ending an existing, “fulfilling” (gross!) friendship when there is potential for cotton-candy-yarn-headed love-love. This is such a weird, defensive dating lie and I hate it! If preserving the friendship takes precedence for either of you, that’s fine (and actually very beautiful because high-stakes friendship gives you life) but that means that there’s not enough real potential for a real relationship anyway because nobody who is super, super into their friend gives a shit about staying that way. If you really like him, think it through, and then act or don’t act, but don’t let your work-life or love-life be determined by circumstance.

More great advice from Kate Carraway: 
Why Do Women Pretend to be Someone They’re Not?
I’m Dating a Woman. What Do I Tell People?
Should I Be Worried About My Guy’s ‘Good Friend’?
Is My Sensitive Boyfriend Just Not All That Deep?
How Can I Make My Boyfriend Initiate Sex More?
We Had the Perfect Date and Then I Never Saw Him Again…
Help! My Boyfriend and I Are From Different Worlds
Help! My Friend Has Become a Selfie-Obsessed Monster
Help! My Girlfriend Is Always on a Diet
Help! My Boyfriend Is Better Looking Than Me
I’m So Tired of Hearing About My Friends’ Boring Babies.
I Have Proof My Friend’s BF Is Cheating. Do I Tell Her?
My Best Friend’s Life Is Perfect. Can I Tell Her to Stop Complaining Already? 
How Young Is Too Young?
Is Long Distance a Dealbreaker?
When Do I Need to Disclose My Dismal $$$ Sitch?
How Can I Curb My Tinder-Rejection Sads?
When Should My Guy & I Talk “Numbers”?
Can We Be FWB When He Wants More?
Is It Ever OK to Date a Friend’s Ex?
How Do I Get Over a Guy?
Why Aren’t I More Obsessed With My BF?
Should I Propose to My Guy?