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How do I pursue a long-distance work crush?

‘Even though I don’t see him in person, I still interact with him virtually’

Love Letters

Love Letters

Q. I’ve been building a friendship for over a year with a co-worker, and I’m just starting to realize I’m catching feelings for him.

We politely and subtly flirt with each other over instant message, and we have talked on the phone quite a bit. He’s in Toronto and I’m in Chicago. Another part that makes it complicated is that he is a co-worker. Even though I don’t see him in person, I still interact with him virtually. I guess my question is, how will I know when it’s the right time to take the online relationship we have into a real meeting to see how we actually feel/interact in person? Also how do I keep this professional without ruining the friendship we already have?



A. I keep thinking of an episode of “The Simpsons” where a character calls Chicago the Miami of Canada. Maybe it is.

There are many reasons to travel to Chicago from Toronto. But I don’t know that people in Boston, let’s say, would be desperate to start a romance with someone in Miami. It’s really far away.

Unless the vibes here are so strong that you’re both texting all the time and figuring out ways to communicate outside of work, on weekends, etc., it would be really difficult to jump to planning a real-life meeting — unless work provides that opportunity.

Can you put a pin in this crush until there’s a real reason to be together for work? If that’s never going to happen, that’s something to note, too. This just seems ... really difficult.

You say you’re not a risk taker, which makes me wonder whether this man is appealing because he involves little risk right now. He’s far away, and even if you try something, he’s still out of reach.


I’m not saying this will never happen. Maybe you can get to a point where there’s an out-of-work Zoom. You could ask for that, I guess — a post-work online drink — just to take a step in a new direction.

But please consider Chicago and all it has to offer. Imagine falling for someone there. That’s the risk that seems worth taking.



So you need a passport to see if you like someone you’ve never seen? Three million people in Chicago.


How “polite” is the flirtation? (How very Canadian.) Would you be embarrassed if your employer read your messages? Just throwing that out there. Just ask him if he’d ever consider visiting Chicago, or the best time of the year to visit Toronto. Do it in a light, playful way. If he’s interested, you’ll know. A recent Love Letters letter prompts me to ask: You guys BOTH know what the other looks like, right?


You can plan a trip up there. Let him know you’ll be in town and see if he suggests a meeting. If he doesn’t suggest a meeting, then you’ll know he’s otherwise engaged or uninterested.


A big part of the appeal is how safe and uncomplicated this relationship is. You are not confronting any reality here — it stays in a gauzy world of social media where neither one of you has to deal with the other’s off days or less attractive qualities. It is perfect because it is not real. The harder part of the equation is risking your career and possibly abandoning your current home to see if you really are compatible. Proximity is an essential ingredient to any relationship and you do not have that, so the risk is disproportionate to the gain of pursuing this any further.



Do you know whether your work crush is single?


He has to be polite, you work together. Co-workers flirt all the time, it’s called distraction and it’s easier/safer with you because you are in a different country.


Nooooo, don’t do anything about these feelings. It would be so creepy to suggest meeting up in person when you’ve never met before, live in different countries, and are CO-WORKERS. Do not do it. Focus that energy somewhere else.


Send your own relationship and dating questions to loveletters@globe.com or fill out this form. Catch new episodes of Meredith Goldstein’s “Love Letters” podcast at loveletters.show or wherever you listen to podcasts. Column and comments are edited and reprinted from boston.com/loveletters.

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