How do I flirt with a coworker safely?

Answer by Marni Kinrys Founder, The Wing Girl Method · 4 min read

Marni's answer

I'm Marni Kinrys, founder of The Wing Girl Method. This one requires nuance because HR is real and misreading a coworker can cost you your job. But not flirting at all when there's mutual interest is also a mistake.

Here's how to do it right without getting yourself in trouble.

The safety rules

Rule 1: Never make the first flirty move at work. Ever. Be warm and friendly with everyone — including her — but don't single her out with anything overt until she's given you clear signs first.

Rule 2: Follow HER lead. If she's finding excuses to come to your desk, touching your arm during conversations, using your name a lot, making prolonged eye contact — those are green lights. Without those, don't push.

Rule 3: Never flirt in front of coworkers, on email, or on any company Slack/Teams. Those are all discoverable. Anything flirty happens in person, one on one, briefly.

Rule 4: Move it OFF work property fast. Coffee outside the building. Drinks after hours. Never let the flirtation be a workplace thing.

How to escalate

1. Friendly baseline. Say hi. Ask how her weekend was. Be warm. Same as with everyone else.

2. Once she's giving flirty signals — respond in kind. Playful teasing. Slight eye contact hold. Nothing sexual.

3. Create a one-on-one moment. Ask if she wants to grab coffee to talk about a project. Or lunch. Or after-work drinks with 'the team' that ends up being just you two.

4. Outside of work, escalate the flirting like you would with any woman. Now you're not in the danger zone.

5. Ask her out ON A DATE — clearly, unambiguously — outside of work. Don't call it 'hanging out.' Make the intent clear.

Trevor and the disaster

Trevor, 31, single, Miami. Thought he was reading flirting signals from a coworker. Started leaving her small gifts on her desk. Sending her direct messages on Teams with winking emojis. Complimenting her outfits loudly enough that others heard.

She reported him to HR within two weeks.

Here's what he didn't realize — she'd been polite to him. That was it. She hadn't touched him, hadn't sought him out, hadn't given ANY of the real flirting signs. He'd projected interest that wasn't there.

Even if it HAD been there — his approach was terrible. Public. Traceable. Escalating without her signals.

The lesson: workplace flirting is high stakes. Be conservative. Wait for CLEAR signals. Move it off work property fast. And when in doubt, don't.

Common mistakes men make

• Making the first flirty move without her signals
• Flirting publicly at work in front of coworkers
• Using company Slack, Teams, or email for anything flirty (all recorded)
• Complimenting her body or outfit at work
• Not moving the interaction outside of work property

What to do instead

• Start as friendly-with-everyone. No special treatment.
• Wait for HER signals — touch, prolonged eye contact, seeking you out.
• Escalate slowly. Casual friendship first.
• Create a one-on-one context OUTSIDE work — coffee, drinks.
• Ask her out clearly outside work. Don't play games with intent.

Marni's take

Here's the thing about workplace flirting. If there's mutual interest, it can absolutely work — many great relationships start this way. But you HAVE to be conservative until she's given clear signals, and you have to move it off work property fast. When in doubt, don't. The cost of a wrong move here is way higher than a wrong move anywhere else.

Key takeaways

• Never make the first flirty move at work. Follow her signals.
• No flirting in public, on Slack/email, or anywhere recordable.
• Move it OFF work property as soon as possible.
• When in doubt, don't. The stakes are too high.