How Do I Pursue A Long-distance Work Crush?

Wednesday | July 13, 2022

Love Letters Relationships

How Do I Pursue A Long-distance Work Crush?

What about your crushes? Your exes? Your feelings? What’s on your mind? Send a letter to [email protected] or use this form.

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

We politely and subtlety 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 coworker. 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?

– Not a risk taker

I keep thinking of a “Simpsons” episode 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.

– Meredith

Readers? Thoughts on how to take a step in this relationship? Am I wrong to say it’d be better to focus on what’s in Chicago?

Relationships

Featured Comment

To date someone that far out is way to complicated to even meet up and date! To date, we must spend a lot of time together in the same area. Why don’t you get on the dating app in Chicago and chat on there?? (since you chat online anyway and catching feelings)

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