How to Flirt With Your Boss

There are a lot of reasons that you might want to flirt with your boss. Maybe you feel a genuine attraction to your boss and are hoping to pursue a relationship, or maybe you've read one of the (hotly debated!) studies suggesting that people who flirt at work are more likely to get ahead. Regardless of your reasons, it's important to know that flirting at work is a risky proposition, and must be handled with care. This article will walk you through assessing the risks, and then give you some tips for flirting with your boss, should you choose to proceed.

Part 1

Part 1 of 2:

Analyzing the Situation

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1
Think about your motivations. You took the time to look up an article on how to flirt with your boss, so you are clearly giving this some thought already. Ask yourself why you want to flirt with your boss? Are you bored? Do you feel an attraction to your boss that you think could develop into a real relationship? Are you trying to gain some kind of advantage or favor in the workplace? Knowing why you are interested in flirting will help you determine if it's worth the risk.
- A bit of casual flirting with your boss might attract just enough extra attention to land you that key assignment you were hoping for, or help you secure a more desirable shift. Of course, this could also backfire depending on the culture of your workplace.
Do you intend to simply flirt and leave it at that, or are you hoping to eventually begin a romantic relationship with your boss? Figure out what your limits are, and don't offer more than you intend to offer. Leading someone on is unlikely to get you anything you want.
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3
Be aware of possible consequences at work. Relationships in the workplace, especially between supervisors and employees, are prohibited in many companies. Getting involved with your boss might put one or both of you at risk for losing your jobs. If your flirting is unwelcome or excessive, you also run the risk of crossing the line from flirtation into sexual harassment, which in many offices can result in immediate termination. Finally, you might run the risk of losing your credibility or reputation for trustworthiness at work.
- Even after-hours interactions with your boss can be used as a legal basis for one or both of you to be fired, so beware!^{[1]XResearch source}
- Research the relationship guidelines in your workplace before proceeding with any workplace flirtations. If they aren't published, ask an HR person for assistance.
- If you are afraid to make these inquiries because you fear that people will gossip, remember that they will gossip even more if you get involved with your boss, so factor that into your decision.
If your flirting doesn't get you in trouble at work, it could still make you very unpopular. Other coworkers might look down on you for flirting with the boss, or become jealous if it looks like you are getting special treatment because of your flirting. You might also suffer from considerable embarrassment if the flirting goes badly, or you do end up in a relationship that doesn't end well.
Gregg Michaelsen, Dating Coach
I advise taking it slowly and focusing on building a friendly rapport first, without outright flirting. Be mindful of the power dynamics and professionalism. Show you care through respect. Tread carefully in approaching it at work.

Part 2

Part 2 of 2:

Flirting with Your Boss

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You've decided that it's worth the risk, and you want to go ahead and flirt with your boss. Now be careful! Since there are so many possible risks, the best approach is to be very sensitive to any responses you might receive for your efforts, and subtle enough with your behavior that you can deny that flirting was your intention if it doesn't go off as planned. Try to flirt without looking like you are flirting.^{[2]XResearch source}
2
Make eye contact. Making and holding eye contact is the first lesson of Flirting 101, and is sometimes the only tool you need to convey your interest in another person.^{[3]XResearch source} Eye contact is an equally effective tool in flirting, and can even make someone feel more attracted to you.^{[4]XExpert SourceMaria Avgitidis
Matchmaker & Dating ExpertExpert Interview. 20 December 2019.}
- Try to catch your bosses eye in a meeting and hold their gaze a bit longer than you normally would.
- When your boss addresses you, be sure to look her directly in the eye when they speak to you.
- Create more opportunities for eye contact by intentionally walking past your boss's office more often, or arranging in person meetings in lieu of phone calls or emails.
- Note that it takes more than a single passing glance to get the message across. It might take between 3 and 13 soulful looks for your boss to realize that you are trying to signal attraction.^{[5]XResearch source}
- Too much eye contact, however, can quickly become creepy, so be attentive to how you are being received. If your boss tries to avoid your gaze or seems shifty or uncomfortable, be sure to back off.
3
Smile. It seems like a simple piece of advice, but there are few things more appealing than a friendly, genuine smile.^{[6]XExpert SourceMaria Avgitidis
Matchmaker & Dating ExpertExpert Interview. 20 December 2019.} Interestingly enough, crow's feet are the marker of a happy, non-forced smile, so don't worry about any wrinkles you may or may not have. Flash your boss a real smile every now and again to let them know that you are pleased to see them.^{[7]XResearch source}
- By definition, it's hard to rehearse a genuine smile, but if you want to see what yours looks like, try thinking of something really funny and then looking in the mirror.
4
Be attentive. Pay close attention when your boss speaks to you and try to act interested, even if you aren't particularly excited about the subject matter. Ask follow-up questions that show you are engaged, and make comments that show your enthusiasm with something like, "Wow, I had no idea!"
- Don't overact on this one. Being genuine is more important than being attentive.
- Mimicking your boss's body language as you talk is a great non-verbal way to show you are paying attention.
5
Work in a casual touch. This is probably the riskiest move you can make when flirting with your boss, but it is one of the most effective ways of conveying your interest. Don't proceed with this unless you are already getting some definitive, positive feedback from your earlier attempts (your boss reciprocates your eye contact and smiles, and seems very attentive to you). ^{[8]XResearch source}
- Offer a handshake and a smile at the end of a meeting.
- Try a gentle, brief touch on the forearm or the shoulder when speaking with your boss.
- If your boss makes a joke, laugh and place your hand on her forearm. Linger for a second before removing it.
- Avoid any overtly affectionate or sexual touching in the workplace. This includes shoulder rubs, hugs, placing a hand on someone's knee, etc. Even if the contact is desired, it could still get your fired.
Flirting with your boss is dangerous territory, so pay very close attention to the feedback you are getting, and take it slow. If your eye contact and smiles are being reciprocated, things are probably going well. If, however, your boss seems to be shifty or brisk around you, or seems to be going out of their way to avoid you, you have likely made them uncomfortable and should abort your flirtations immediately.^{[9]XExpert SourceMaria Avgitidis
Matchmaker & Dating ExpertExpert Interview. 20 December 2019.}
7
Avoid actions you can't take back. You might send a flirty text message or email to someone you are interested in outside of work, but written communication is hard to take back or ignore if things go awry, and should be avoided in a workplace flirtation or romance. You should also avoid obviously flirting in front of other people.
- Remember that in many cases, your employer has the right to track and examine any emails you send or receive using a company-owned computer, or even texts and calls made from a company phone.^{[10]XResearch source}
- If your flirting is reciprocated and does proceed to the texting/emailing stage, remember to conduct your interactions using your personal computer and/or phone, and email accounts.
8
Be honest and direct. If things go well, someone will eventually have to make a move if the relationship is going to progress. Because of the complexities involved in a workplace relationship, it is better to talk about the situation up front rather than plunge ahead with an overtly sexual advance. Be direct and honest about your intentions, and give your boss a chance to respond. It may feel awkward, but it's important to be certain that you are both on the same page before things go any further.
- Ask your boss to join you for coffee or lunch, and bring up the subject there.
- Broach the subject gradually, and leave yourself an exit in case you misread the situation.
- For example, you might begin with some work-related small talk and work towards the inquiry: "What do you think about office relationships?" Your boss's answer to this should give you a pretty clear indication as to whether you should proceed or back off.
- Remember: if it turns out you misread things and your boss is not interested, you will have a lot less to be embarrassed about from a straight-forward conversation than if you had attempted to kiss them, or worse.

Expert Q&A

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Question
What should I do to attract attention?
Maria Avgitidis
Matchmaker & Dating Expert
Maria Avgitidis is the CEO & Matchmaker of Agape Match, a matchmaking service based out of New York City. For over a decade, she has successfully combined four generations of family matchmaking tradition with modern relationship psychology and search techniques to ensure her professional clientele are introduced to their ultimate match. Maria and Agape Match have been featured in The New York Times, The Financial Times, Fast Company, CNN, Esquire, Elle, Reuters, Vice, and Thrillist.
Maria Avgitidis
Matchmaker & Dating Expert
Expert Answer
If you want to attract attention, you can smile and make eye contact with them. Show them that you are open to talking.
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Question
What colors can make me look more attractive?
Maria Avgitidis
Matchmaker & Dating Expert
Maria Avgitidis is the CEO & Matchmaker of Agape Match, a matchmaking service based out of New York City. For over a decade, she has successfully combined four generations of family matchmaking tradition with modern relationship psychology and search techniques to ensure her professional clientele are introduced to their ultimate match. Maria and Agape Match have been featured in The New York Times, The Financial Times, Fast Company, CNN, Esquire, Elle, Reuters, Vice, and Thrillist.
Maria Avgitidis
Matchmaker & Dating Expert
Expert Answer
If you are a woman, wear blue, green, or red, instead of purple or black. These colors get a higher rate of response from men.
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Question
How can I know that I am not saying the right things while flirting?
Maria Avgitidis
Matchmaker & Dating Expert
Maria Avgitidis is the CEO & Matchmaker of Agape Match, a matchmaking service based out of New York City. For over a decade, she has successfully combined four generations of family matchmaking tradition with modern relationship psychology and search techniques to ensure her professional clientele are introduced to their ultimate match. Maria and Agape Match have been featured in The New York Times, The Financial Times, Fast Company, CNN, Esquire, Elle, Reuters, Vice, and Thrillist.
Maria Avgitidis
Matchmaker & Dating Expert
Expert Answer
You can know that you are not saying the right things while flirting by observing their body language. If they do not contribute to the conversation, start taking steps back, or start nodding more, you can understand that you are going off the track.
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