Dear Giacomo: Office Romance

Nonprofit master Giacomo Crostini is here to answer all your burning questions about life in the nonprofit sector. Email him at [email protected] for advice and guidance.

giacomo.jpgDear Giacomo,

I’ve got a crush on a major hottie at work - yowza! I love his passion for our cause and the flirting has gone up a few notches the last few weeks. I’m thinking about making my move. Any advice on how to navigate workplace dating?

Single And Saucy and Super Yolo


I can’t tell you how happy I am to get this letter from you. It’s a topic near and dear to my heart. Statistics vary, but the overwhelming consensus is that it’s pretty likely you are going to date someone you work with at some point in your life. It’s not surprising - we spend a lot of time at the office these days, and that lends itself to getting to know our co-workers really well. Many advice columnists will tell you to steer clear of office romance or at the very least to tread lightly. I’m here to tell you that they are completely wrong! Follow my 3 simple steps and you, your hottie, and your boss will all be laughing over champagne at your rehearsal dinner in no time at all. Or maybe not. Read on!

Amazing piece of advice #1: Clear Expectations!

dating.jpgLet’s be real here. A bombed office relationship is AWKWARD. Like so so so awkward (unless you work at a summer camp, tanning salon or restaurant where everyone dates everyone at some point. I’ve got a whole other advice column for places like that). For our purposes SASSY, let’s assume that you work in a more traditional office setting. If you are going to make that move, make sure you both have a very honest conversation early on about what this relationship is going to be. Are you looking for Mr. Right or Mr. Right Now (see what I did there)? If he’s shopping for rings or drawing hearts on his Trapper Keeper and you’re ready to take that foxy new hire out to lunch things could get messier than my hermit crab habitat after I forget to replace the sand for a few weeks. Pow! It’s always better to have clear guidelines on where things are at for both of you, sort of like an office romance pre-nup! You don’t have to make it too intense - but at least that way you aren’t daydreaming about sporking him in the eye when he’s chatting a little too flirtatiously with Harriet from Accounting. Harriet. UGH.

Amazing piece of advice #2: Follow the rules!

expectations.jpgRules you say?! What rules? Love doesn’t have rules! Sorry Charlie, er, I mean SASSY, but most organizations do have a policy of some sort about dating co-workers. Don’t worry - these rules are made to protect you and your colleagues! For instance, you probably want to avoid that pesky Supervisor/Employee relationship - that’s pretty much got bad news written all over it. Most organizations have a written policy in your Human Resources handbook that outlines the expectations around this - you may have to disclose the relationship to the HR department at a certain point or there may even be a policy prohibiting a relationship at all. What I’m trying to say is, you better check yourself before you wreck yourself! Being aware and in the know on your specific workplace rules and guidelines is the best way to make sure that your potential love can blossom into the beautiful flower we both know it will most likely be - because let’s face it, you’re a catch!

Amazing piece of advice #3: Keep it freshy fresh! (But don’t make it weird)

OfficeDatingMen1.jpgOk SASSY - have you checked your HR policies and had an honest conversation with that big hunk? Then it’s time to enjoy this new relationship! Just remember that the responsibility lies on you to make sure you aren’t creating a situation that makes your colleagues uncomfortable in any way. This means not accidentally sending all staff emails about how cute his bedhead hair looked this morning! Oops! Been there, done that, no fun! This may seem a bit personal but here is a brief list of bullet points I have found to be incredibly effective for keeping the romance alive:

  • Tired of trying to find the right words to express your feelings? Use gifs! They are fun and there are perfect ones for any emotion/situation!
  • Have a pet? There is nothing quite like a nice evening with your favorite animal friends! I can’t tell you how nice it is to just let my hermit crabs out of their habitat to roam around while me and my sweetie watch a romcom and snuggle.
  • If all else fails, break out your writing chops, put some words next to each other that rhyme and compose a little ditty. Don’t think you have what it takes? Just search “Awkward Love Song” on Youtube and you can see that people are doing this every single day - join in! You could go viral!
  • Have you ever been to a bad pool party? I haven’t! I’ve got a sweet hook up on slip ‘n slide rentals for a very reasonable price, so feel free to reach out if that sounds like something up your alley.

pool.jpgAt the end of the day just be smart about how you approach office romance and make sure you are protecting yourself by doing a little legwork in advance. If you are still nervous about it, there have been billions (that number is estimated) of articles and books written on this, many of which can be found online. The advice you find can be across the board, so make sure you do what is best for you and follow the rules for your organization. I put a few links below to start you off. Now get out there and make me proud!
Have some additional office relationship advice you want to share with the YNPN-TC community? Tweet it  at @ynpntc and use the hashtag #deargiacomo.

Original artwork by Taylor Baldry

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