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.
Flip through those pages (or, let’s be real, Ctrl+F the PDF) and look for terms like “fraternization” or “relationship.” If the policy is a hard no, you’ve got a choice: keep your crush a fantasy or start polishing your LinkedIn profile for a new gig. If there’s wiggle room, proceed to the next step, but tread lightly. You don’t want to be the reason HR starts sending out “reminder” emails about professionalism.
Step 2: Assess the Risk Like You’re Playing Office Chess
Dating a coworker isn’t just about butterflies and first kisses; it’s a high-stakes game of office politics. Reddit user CryAcademic7534 put it bluntly: “Don’t date coworkers, especially if it’s a place you enjoy working at and plan to stay there for a long time.” They’re not wrong. A failed romance can turn your dream job into a daily cringe-fest where you’re dodging your ex in the break room like it’s a game of corporate hide-and-seek.
Ask yourself some hard questions
Do you work closely together?
If you’re on the same team or share a cubicle, a breakup could make every meeting feel like a reality show reunion special. Harvard Business Review suggests considering whether you could both stay professional post-breakup. Picture your last messy breakup—could you have collaborated with that ex on a project? If not, maybe keep this crush on the back burner.
Are they single?
This seems obvious, but don’t assume. Check their social media (discreetly, not like a private investigator) or pick up on context clues in conversations. Nothing says “awkward” like asking out someone who’s already spoken for.
What’s the power dynamic?
If they’re your boss or subordinate, just don’t. Power imbalances are a recipe for disaster, not to mention a potential HR nightmare. Even if you’re peers, consider how your roles might intersect. If one of you gets promoted later, things could get messy faster than a spilled coffee on a white shirt.
If the risks feel manageable, you’re ready to move forward. But if your gut’s screaming “abort mission,” listen. There are plenty of fish in the sea who don’t share your office Wi-Fi.
Step 3: Build a Connection (Without Being Creepy)
You can’t just waltz up to your coworker and drop a “Wanna grab dinner?” like you’re in a rom-com. You need to lay some groundwork first. Think of it like planting a garden—you don’t just throw seeds at the dirt and hope for roses. Start by building a friendly, professional rapport.
Find common ground.
Maybe you both love the same niche podcast or roll your eyes at the same outdated office printer. Use these as conversation starters. “Hey, did you catch the latest episode of Serial Ink Cartridge Nightmares?” can lead to a chat that’s flirty without being overt.
Keep it low-key.
Reddit user Zaphod_Beeblbrox2024 suggested a casual “Hi, would you like to grab some coffee with me sometime?” This is a solid start, but make sure it’s clear you mean outside the office cantina. A coffee invite is perfect because it’s low-pressure and doesn’t scream “I’m planning our wedding.”
Read the room.
Are they making prolonged eye contact? Laughing at your terrible puns? Lightly touching your arm during a chat? These are green lights, according to dating coach John Keegan. But if they’re giving one-word answers or sprinting to the elevator to avoid you, take the hint.
The goal is to establish that you’re a human they enjoy being around, not just the guy who always hogs the good stapler. Take your time—rushing this step is like microwaving a steak. Sure, it’s faster, but the results are… not great.
Step 4: Make Your Move
When you’re ready to ask them out, channel your inner James Bond: smooth, confident, and with an exit strategy. Here’s how to do it without triggering an office-wide gossip storm:
Choose the right moment.
Don’t ask them out during a team meeting or when they’re frantically finishing a deadline. Catch them during a quiet moment, like when you’re both grabbing coffee or chatting after a meeting. Privacy is key—you don’t want Karen from accounting live-tweeting your attempt.
Keep it clear but casual.
Try something like, “Hey, I really enjoy talking with you, and I’d love to get to know you better outside of work. Would you be up for grabbing coffee this weekend?” This is direct enough to avoid the “is this a date or not?” confusion but chill enough to keep things relaxed.
Respect their response.
If they say yes, awesome—plan that coffee date and keep it professional at work until you’re sure where things are going. If they say no (or give a vague “maybe later”), smile, say “No worries,” and back off. Google and Facebook have an “ask once” rule for a reason—repeated asks can cross into harassment territory, and nobody wants to be that guy.
Pro tip: Avoid grand gestures. No roses on their desk, no serenading them in the break room. This isn’t The Bachelor—it’s your workplace. Keep it subtle to avoid making them (or your coworkers) uncomfortable.
Step 5: Navigate the Aftermath Like a Pro
Whether they say yes or no, you’ve just opened Pandora’s box, so handle the fallout with care.
If they say yes
Congrats, you’ve got a date! But don’t start holding hands in the office or sneaking kisses by the copier. Keep your work behavior so professional it could star in a corporate training video. No PDA, no bickering, and definitely no oversharing with coworkers. As Early magazine points out, even casual offices frown on couples who make others question their judgment. If things get serious, check in with HR about disclosure policies to cover your bases.
If they say no
Don’t take it personally. Reddit user Purple_Plum8122 dropped a truth bomb: “Coworkers are forced to be nice to each other. It does not mean they like you.” Ouch, but fair. Keep your interactions friendly but professional, and don’t let rejection turn you into the office grump. If it’s too awkward, focus on your work and give it time—the sting will fade.
In either case, don’t fuel the office gossip mill. If coworkers start sniffing around, deflect with a vague “Oh, we just grabbed coffee” or “We’re just friends.” The less you say, the less likely you are to end up as the subject of the next team happy hour debate.
Step 6: Prepare for the Worst (Because Reddit Says So)
Reddit’s collective wisdom leans hard into the “don’t do it” camp, and they’ve got a point. User niceshootintex’s “I shat where I ate not once but twice” is a cautionary tale wrapped in regret. So, let’s game-plan for the worst-case scenarios:
The breakup
If you date and it ends, you’ll still see them every day. Can you handle that? If not, start browsing job listings now. If you think you can, set ground rules early about how you’ll handle a potential split. Agree to keep it professional and avoid dragging coworkers into your drama.
The gossip
Offices love a scandal, and your romance could become the main course. Keep your relationship private, especially on social media, and don’t give coworkers ammo. If someone asks nosy questions, channel Ask a Manager’s advice: redirect the conversation to work or change the subject entirely.
The career hit
If things go south, your professional reputation could take a hit. Coworkers might question your judgment, and managers might hesitate to promote you if they think you’re distracted by personal drama. Stay on top of your game—deliver stellar work, meet deadlines, and don’t give anyone a reason to doubt your focus.
The Golden Rule: Don’t Be That Guy
At the end of the day, the key to asking a coworker out is to be respectful, professional, and prepared for any outcome. Reddit user DolphinPussySlayer’s “Hey wanna fuck?” approach might get a laugh, but it’s also a one-way ticket to HR. Instead, take the high road. Be clear about your intentions, respect their boundaries, and keep your work life separate from your love life.
If you’re still on the fence, consider Reddit’s blunt wisdom: “You don’t.” Maybe they’re right, and your soulmate is waiting at a coffee shop or a dog park instead. But if your heart’s set on this coworker, follow these steps, keep your cool, and maybe—just maybe—you’ll get that coffee date without torching your career.
Now go forth, flirt cautiously, and don’t forget to check that employee handbook. Good luck, you brave, lovesick fool.
