How to Flirt with a Guy at Work

Co-authored by John Keegan and Danielle Blinka, MA, MPA

Last Updated: July 27, 2022 References

Do you have a little crush on one of your coworkers? Flirting in the workplace can be fun, but it can also be risky. The last thing you want is to get in trouble with your boss or HR. Fortunately, you can subtly flirt with him using your body language, showing off your personality, and complimenting him. Just make sure that you're following all of your workplace's rules and respecting his boundaries so you don't tarnish your professional reputation.

Method 1

Method 1 of 3:

Using Body Language

1
Make eye contact with him when he's around you.^{[1]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 5 November 2019.} Looking directly into someone's eyes creates an instant connection. When you make eye contact, hold it for 1-3 seconds so he feels noticed. Then, smile and look away. This is an easy way to flirt with your workplace crush without it being obvious.^{[2]
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- Don't stare into his eyes for longer than a few seconds. Otherwise, he might feel uncomfortable.
- If you feel awkward or he asks if you need something, ask him a generic work question. You might say, “Did you get my email?” “Did you see the new quarterly numbers are out?” or “Do you know if the printer is fixed?”
2
Smile when you see him.^{[3]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 5 November 2019.} Flashing someone a smile is the simplest, easiest way to flirt with them. Whenever he looks at you, give him a wide grin or a sly half-smile. Additionally, fix a smile on your face anytime he's going to be in the room.^{[4]
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- A toothy grin makes you seem like you're a fun person, while a sly smile makes you seem mysterious.
Tip: Practice smiling in the mirror so it'll be easier to give a flirty smile when you see your crush.

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3
Wink at him playfully when no one else is watching. Giving a sly wink will send him a clear signal that you're feeling flirty. However, you can also explain it away if the situation becomes awkward. Wait until no one's around or you feel confident that no one is looking. Then, wink at him as you pass each other.^{[5]
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- A slow wink is more flirty than a quick wink.
- If you're not sure how he'll react to the wink, start with a quick wink so that it's easy to explain away. You could say, “I think I got something in my eye. I'm going to check in the mirror.”
4
Brush against him to break the touch barrier.^{[6]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 5 November 2019.} Physical contact definitely takes your flirting to the next level, but touching a coworker can be a minefield. Play it safe by gently brushing past him or bumping into him. That way, you can play it off as an accident if things get weird.^{[7]
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- For instance, you might “accidentally” bump against him while you're passing him in the hallway. Then, say something like, “We can't keep meeting like this,” or “Sorry about that!”
5
Touch his arm while you're talking to him. You should be able to get away with a little arm touching in the workplace. While you're talking to him, lightly touch his forearm or bicep. Make quick, gentle touches that don't last longer than 2-3 seconds.^{[8]
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- Stop touching him if he pulls away or looks uncomfortable. Instead, create some distance between you and say something like, “Sorry about that. I'm just really focused on this project.”
6
Be sensual by walking by slowly and accentuating your movements. This is an easy way to cultivate sex appeal in the workplace without being obvious. Men love watching your body move, and slowing down makes it more eye-catching. Move slowly and make your regular movements bigger when he may be watching you. This should get him to stare at you and lets you covertly flirt with him.^{[9]
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- For example, slowly strut by his desk whenever you walk across the room.

Method 2

Method 2 of 3:

Drawing His Attention

1
Dress well but keep your look professional. When you're trying to get a guy's attention, you want to look your best. However, it's important that you stay in dress code at all times so you don't compromise your job and career path. Choose professional outfits that make you look and feel your best but will also impress your boss.^{[10]
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- If you're a woman, you might wear a pencil skirt with a silk blouse or a pair of fitted slacks with a structured top.
- If you're a man, you might wear a tailored blazer or pair a unique tie with your button-up shirt.
2
Ask him to help you with an issue you're having. Getting help from someone is a classic flirting maneuver that's easy to brush off as innocent. If you're able to collaborate at work, invite him to work on a project with you. As another option, ask for his opinion about something. This allows you to talk to him while still keeping it professional.^{[11]
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- You might say, "Hey, can you help me with this client pitch?" or "Do you have time to partner with me on this project?"
Tip: If a conversation starts, try to keep it going. To do this, ask open ended questions like, “What did you do next?” or “How are you dealing with that?” It's possible that he'll see this as an opportunity to flirt with you, as well.
3
Learn more about him by observing him and asking questions. When you're working with him, use it as an opportunity to learn more about him. Look for a wedding ring, check his workplace for photos of a partner, or work in questions about his personal life. Only ask 1-2 questions at a time so that he doesn't realize you're fishing for information.^{[12]
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- For instance, you might go talk to him right before he gets off work so you can say, “You know what, I can come back tomorrow. I don't want to make you late for dinner with your girlfriend.”
4
Show off your personality by mentioning your hobbies and interests. Talking about yourself may not seem like flirting at first glance, but it can get his attention. Rather than telling long stories about your life, briefly mention the most interesting things about yourself when you have the opportunity. Try to relate it to your work so it seems innocent.^{[13]
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- For instance, let's say you have a demanding workload this week. You might say, “I won 1st place in a marathon last year, so I'm used to going all the way.”
- If you're allowed to display personal photos in your work area, include pictures that show you enjoying your favorite activities. This might include a photo of you hiking, a picture of you working on a painting, and a snapshot of you reading at the beach.
5
Try to make him laugh. Using humor is a common flirting tactic that's easy to use in the workplace. Practice your funniest life stories so that you can dazzle your crush with them, or learn a few corny jokes from the Internet. You might even send him memes that are related to the work you do.^{[14]
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- Try these jokes: “Have you been to that new restaurant called Karma? There's no menu because you get what you deserve.” “Do you know why the robber took a bath? He wanted to make a clean getaway.” and “What is an astronaut's favorite place on a computer? The spacebar.”
6
Compliment him to show him that you've noticed him. Start with professional compliments to test the waters. If he seems receptive, try complimenting something about his looks. However, take your time so that you don't come on too strong.^{[15]
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- Start with compliments like, “That was a great presentation,” or “I'm always happy when I get to work with you because you're so dedicated.” Then, try, “That shirt looks great,” or “Looking stylish today!”
- If he seems uncomfortable, brush off the compliment and leave him alone. You might say, “I'm trying this new thing where I pay it forward with compliments, but maybe I'll try buying someone a coffee next time.”
Tip: Try phrasing compliments about their looks as a joke. Say something like, “Wow, even when it's raining your hair still looks perfect.” This allows you to see how he reacts while still being able to act like it wasn't meant as a compliment.^{[16]
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7
Send carefully worded texts or emails if he seems receptive. Flirting via messages is usually an easy, convenient way to make your feelings known. However, it can be risky at work because it leaves a record of your flirtations. Additionally, it's easy to misread the tone of a text. However, you can send him slightly flirty texts or messages if you think they'll be well-received.^{[17]
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- For example, you might text him a winky face or “Looking good!” after you pass him in the hallway.
- Similarly, let's say that he's sent you an email asking for a meeting later in the day. You might respond with, “Oh, I'd never miss an opportunity to see you.”
Tip: Before you send something, ask yourself if you'd be okay with another coworker or HR reading what you wrote. Don't risk your job!

Method 3

Method 3 of 3:

Protecting Your Professional Reputation

1
Check your workplace's policies about employee relationships. Some workplaces allow employees to date, while others forbid it. It's important to know where your workplace stands so you don't land yourself in trouble. Read your employee handbook to learn about the policies. If you have questions, talk to your HR rep.^{[18]
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Trustworthy Source
Harvard Business Review
Online and print journal covering topics related to business management practices
Go to source}
- Don't rely on the office rumor mill for your information. It's possible to get misinformed.
- If dating is allowed, make sure you know all of the rules. For instance, you might need to disclose your relationship and probably can't date your supervisor.
Tip: If you're only flirting for fun, you might not worry about the relationship policies. However, you still want to be careful that you don't step over the line.
2
Don't flirt with your boss or the people you supervise. This is problematic for multiple reasons. First, most companies don't let supervisors date the people under them, so this will put someone's job in jeopardy. Additionally, it may trigger rumors that you're trying to advance your career or could get you accused of sexual harassment. Save yourself a headache and leave your supervisors and direct-reports alone.^{[19]
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Trustworthy Source
Harvard Business Review
Online and print journal covering topics related to business management practices
Go to source}
- If you really want to date them, apply for a transfer so that you won't be directly under or above them anymore. Until then, keep things totally professional.
3
Respect the boundaries that your coworker sets.^{[20]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 5 November 2019.} While it's possible that your coworker will enjoy the flirting, he could become uncomfortable. Try not to take this personally because it's possible he just doesn't want an office relationship. At the same time, give him his space and stick to workplace talk when you interact with him in the future.^{[21]
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Trustworthy Source
Harvard Business Review
Online and print journal covering topics related to business management practices
Go to source}
- Don't completely avoid him or stop talking to him altogether. This can make the situation uncomfortable and may hurt your working relationship.
4
Don't touch your coworker anywhere other than their arm. While touching is a great way to flirt, it's not always appropriate in the workplace. Don't touch his back, shoulders, legs, or anywhere else while trying to flirt. This can quickly lead to a harassment complaint, so play it safe.
- If you and your crush start dating, it's okay to touch him more. However, keep workplace public displays of affection (PDA) to a minimum to avoid appearing unprofessional.
5
Avoid references to sex or suggestive comments. While being suggestive is normally a good way to flirt, it's a liability when you're at work. Don't risk your career to get this guy's attention. Keep your flirting strictly PG.
- Again, it's okay to get a little naughty if you and he start dating. However, don't talk about sex at work.
6
Be careful about what you say in a text, email, or social media post. If there's a record of your flirty behavior, you're at a greater risk for landing in trouble. Don't send any messages at work that you don't want to be read by another coworker. Your career is important, so don't mess it up over a guy.^{[22]
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- If you're in doubt, don't hit send.

Expert Q&A

Question

How can I subtly flirt with someone at work?

John Keegan
Dating Coach
John Keegan is a dating coach and motivational speaker based in New York City. He runs The Awakened Lifestyle, where he uses his expertise in dating, attraction, and social dynamics to help people find love. He teaches and holds dating workshops internationally, from Los Angeles to London and from Rio de Janeiro to Prague. His work has been featured in the New York Times, Humans of New York, and Men's Health.

John Keegan

Dating Coach

Expert Answer

If you like them, casually brush up against them when you walk past to show you're interested. Start talking to them more and offering compliments.

Warnings

Be really careful when flirting at work. Some people can interpret flirting as sexual harassment, which is serious.

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Don't flirt with more than one coworker at a time, as it could lead to an uncomfortable situation.

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If your coworker asks you to stop, do so immediately and respect his boundaries.

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