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How to Ask a Coworker on a Date Without Setting Your Career on Fire
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How to Ask a Coworker on a Date Without Setting Your Career on Fire

Maria Lavrov Cain Maria Lavrov Cain April 27, 2025 7 min read
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Crushing on a coworker? Navigate the office romance minefield with our guide. Learn how to ask them out subtly, assess risks, and keep it professional—without turning your workplace into a soap opera.

How to Ask a Coworker on a Date Without Setting Your Career on Fire
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So, you’ve got a crush on a coworker. Your heart does a little flip every time they walk by with their reusable coffee mug, and you’re pretty sure their spreadsheet skills are the stuff of legends. You’re thinking about asking them out, but the Reddit hive mind has spoken, and the consensus is clear: “Don’t shit where you eat.” Harsh? Maybe. True? Probably. But let’s not give up on love just yet. Instead, let’s navigate this minefield with the finesse of a cat burglar.

Step 1: Check the Employee Handbook (Yes, Really)

Before you even think about sliding into their DMs or lingering too long by the water cooler, do your homework. Your company’s employee handbook is the ultimate buzzkill, but it’s also your first line of defense. Many workplaces have policies on office romances, ranging from “absolutely not” to “proceed with caution.” Some might require you to disclose a relationship to HR, while others might just frown upon it like your grandma catching you sneaking cookies before dinner.

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