How to Flirt at Work

Co-authored by Mark Rosenfeld

Last Updated: October 21, 2021 References

Developing a flirtatious relationship with someone at work can make long days breeze by, and the prospect of running into your crush during trips to the coffee machine can certainly be entertaining. But you don’t want to overstep boundaries and put your career in jeopardy. There’s a fine line between work-appropriate flirting and setting yourself up for disaster. Whether you’re hoping to begin a new flirtation with a colleague, or take it to the next level, these tips for creating an appropriate workplace flirtation will save you a lot of embarrassment and keep your professional reputation intact.

Part 1

Part 1 of 3:

Attracting The Attention of a Coworker

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Don't get thrown into the friend zone. Since you'll only be seeing her during the time that her brain is in work-mode, you'll need to work extra hard for her to see you in a new light. Share things about yourself so that she sees you as a real person, rather than just a colleague.^{[1]
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- Let her know that you are taking improv classes on Wednesday nights or that you go mountain biking on the weekends.
- Without making it obvious, hint to her that you're single, and therefore available.
- Studies show that it's possible to create chemistry between two people.Try gently teasing her about her cute dimples.
- Develop inside jokes. If you have a favorite show in common, try quoting it or sending her trailers for the upcoming season.
2
Gain her respect. Few things garner the attention of a colleague more than professional success, so show her what an all-star you are at your job. By doing so, you’ll most likely receive praise by those who work alongside you, which is bound to get back to her. If you win awards or implement successful projects, she'll not only notice you, but will view you in a positive light. She may even refer to you when she has a question.^{[2]
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- Help others, especially your crush, in your area of expertise. This will give you an opportunity to subtly show off your skills, while proving how helpful you can be.
- If nothing else, this tactic will strengthen your career.
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3
Laugh at her jokes. Making her feel good about herself is a sure way to catch her attention. She will immediately feel comfortable around you and will open up more. It will also show her that you have something in common and it will continue to be easier to break the ice.^{[3]
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- This doesn’t mean you should laugh at every single thing she says, you don’t want to come off as fake.
- Make a few jokes to prove that you have a sense of humor of your own.
- Remember, the point is to put a smile on her face, so even corny jokes will do. Try: "What does a nosy pepper do? Gets jalapeño business."
- Sending her small jokes throughout the day is a great way to give her a pick me up, and she'll smile whenever she sees a message from you.
4
Liven up your appearance. It will be difficult to catch her attention if you look like you just rolled out of bed that morning, and you'll never be able to leave the friend zone. Go for a mix of professional and sexy. Your clothing should display your best assets while conveying that you take your job seriously.^{[4]
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- If you've been told that the color blue brings out your eyes, wear something with blue in it.
- This doesn’t mean showing too much skin, remember you should still be office-appropriate.
- For women working in a casual office environment, instead of jeans wear a dress or skirt and put on some make-up so you'll stand out.
- Men should consider a collared shirt rather than a t-shirt. Likewise nice slacks and a tie are sure to make her notice how put together you look.
5
Be approachable. If you’re waiting for your crush to make the first move, looking lost in an excel document or constantly having your headphones on is a bad move. It’s beneficial to have a good rapport with co-workers, so show her how friendly you are with those around you, and she’ll be more likely to engage you in conversation. Make sure to go out of your way to include her in chats you're having with other colleagues. Paying attention to her in this way will not only flatter her, but will show that you value her input.^{[5]
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Mark Rosenfeld
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Expert Interview. 11 June 2021.}
- Smile and be warm during your interaction.

Part 2

Part 2 of 3:

Flirting With Your Office Crush

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Initiate casual chat through email, instant messaging, or when you see her around the office. This would also be a good time to show her how clever you are. Nothing wins a person over more than wit and humor. Put that joke we talked about to good use. ^{[6]
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- Don’t limit your communication to the web, make sure you supplement it with in-person interaction.
- When you're waiting for your tea to brew or in line for lunch, ask what her plans are for the weekend or if she's been to any movies lately.
- Make it a habit to swing by her desk in the morning to ask how her day is going or what she did the night before.
- Smile and keep eye contact. This shows you’re confident and assertive.
- Give her subtle, under the radar, compliments to show that you’re interested. Let her know that you noticed her new haircut or glasses, or even that she did a good job on the presentation this morning.^{[7]
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  Expert Source
  
  Mark Rosenfeld
  Dating & Relationship Coach
  Expert Interview. 11 June 2021.}
2
Be all ears. People love to commiserate, so whether it’s listening to her complain about a mutual coworker or covering for her when she’s out of town, be a reliable confidante. This will make her trust you and eventually you’ll develop a real camaraderie.^{[8]
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- Gain her trust by asking open-ended questions, voicing your own opinions about what she says, and repeating some of it. This also shows that you're listening.
- Communicate some personal information of your own so she's likely to continue to open up to you.
- Never relay what she shares with you to anyone in the office.
- Don’t take the petty banter too far, you don’t want to give the impression that you’re shallow or unkind.
3
Before you make your latte run, ask if you can bring her back a coffee. This is the best way to catch her attention without coming off as too aggressive. It will also give her the opportunity to accompany you if she’s interested.^{[9]
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- This means more face time and getting to know each other on a personal level.
- Remember how she likes her coffee, and have it waiting on her desk in the morning once in a while.
4
Ask her for advice or help on a project you’re working on. There’s nothing wrong with in-office collaboration, and if this means getting your cute counterpart to help you make a deadline, more power to you. Be humble and admit that you don't know something. She'll feel useful by teaching you something, giving her the opportunity to shine.^{[10]
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- Working on something together will help the two of you bond.
- Your crush will feel self assure and capable, making her more likely to open up to you.
- Show her you appreciate her support and boost her confidence by praising her work in a genuine way.
5
Walk her out. Leave the office at the same time, so you can take the elevator together and possibly walk her to her car or the subway station. This will prove that you’re polite and give her the hint that you’d like to spend more time with her.^{[11]
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- Offer your crush a ride home if you have a car.
- If you happen to live off the same subway line as her, remember there is no better opportunity for flirting than during your evening commute, so suggest riding the train together.
6
Initiate an office happy hour. If you’d like to spend time together outside of the office, planning a group activity is the way to go. You won’t have to worry about this seeming like a date if you’re sure to include at least two or three other co-workers.^{[12]
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- Once both of you are able to loosen up outside of the office, she might just see you in a whole new light.
- Take the opportunity to focus on non-work topics and do what you can to find common ground, so she'll want to continue to spend time with you away from the office. For instance, ask her what countries she's travelled to or what kind of music she likes.
- A drink or two may have you feeling comfortable enough to make a move by inviting her out on her own next time.
7
Pursue a flirtation with one only co-worker at a time. You don’t want to get a bad reputation around the office and for your work to suffer because of this. If your crush, or others, get the idea that you're not trustworthy, they might question your work integrity as well.^{[13]
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- Nothing will turn off a potential work crush more than if she gets the idea you’re disingenuous.
8
Be conspicuous and keep your flirting sessions under wraps. The last thing you want to do is get her into trouble. Refrain from the teasing or joking from previous steps if you're in front of other co-workers. Furthermore, the conversations you share will feel more meaningful if kept just between the two of you.^{[14]
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- This will save both of you from potential embarrassment or running into issues with Human Resources.
- Be sure to research your company's policy on in-office romance before you tell anyone about your office flirtation.
- She’ll respect you more for being protective of her reputation.

Part 3

Part 3 of 3:

What Not To Do

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Do not flirt with your superior. This could jeopardize your reputation and get you fired. Doing so could give the wrong impression to not only your boss, but peers as well. People might conclude that you don't respect your superior and don't take your job seriously. If your boss does initiate a flirtation with you, it is usually still a good idea to rebuff advances for the sake of your reputation and career.^{[15]
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- Your manager may be insulted and assume you are merely trying to further your career.
2
Don’t get too touchy. Others watching may find it uncomfortable, or even feel snubbed. The last thing you want to do is distract your office mates from their work because you and your crush can't keep your hands off of each other. Furthermore, If your crush isn't interested, physical contact could intimidate and turn her off.^{[16]
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- If a colleague determines that you're giving special attention to someone in the office, they may feel jealous and bitter. This could lead them to get managers involved.
- If you happen to misread the situation, you could mistakenly get flagged as the “office creep.“
3
Don’t pursue a flirtation if someone is likely to get hurt. If you’re only looking for an office fling, but know your crush is hoping for a substantial relationship, stick to a friendship. Dealing with the awkwardness of differing expectations isn’t worth facing everyday when you go into the office. If you are unsure, find a trustworthy office mate who might know your crush's situation before you make any moves.^{[17]
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- Avoid pursuing anyone who is married or involved in a relationship.
4
If things do progress between the two of you, keep it clean. Refrain from using risky language while logged onto your professional phone or email accounts. Likewise, any physical encounters should be carried out away from the office. Mixing your personal life, especially if it involves a colleague, is unprofessional and could get you into trouble by your company.^{[18]
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5
Don’t let an office romance get in the way of your professional obligations. If the quality of your work is suffering, and you’re finding yourself putting a flirtation before deadlines, it’s time to refocus your energy.^{[19]
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- There is a time and place for flirting, so while lunch breaks and coffee runs can be great for it, always remind yourself what’s important, or you might find yourself without a job.
- If you do find this happening, it's could be a great excuse to initiate spending some time together outside of the office.

Expert Q&A

Question

How do you subtly flirt with a guy at work?

Mark Rosenfeld
Dating & Relationship Coach
Mark Rosenfeld is a Dating and Relationship Coach for women and founded Make Him Yours in 2015. Mark specializes in helping people find, attract, and keep extraordinary relationships. He has been featured in Style Magazine, Thought Catalog, Elite Daily, News.com.au, and The Good Men Project. Mark’s dating videos have received over 60 million views, and his book “Make Him Yours – Beating the Odds of Modern Dating” was a best-seller on Amazon on its release.

Mark Rosenfeld

Dating & Relationship Coach

Expert Answer

Innuendos and little touches can be really powerful. If you don't feel comfortable making innuendos, try to have fun in your conversation by being touchy and flirty.
Question

What is subtle flirting?

Mark Rosenfeld
Dating & Relationship Coach
Mark Rosenfeld is a Dating and Relationship Coach for women and founded Make Him Yours in 2015. Mark specializes in helping people find, attract, and keep extraordinary relationships. He has been featured in Style Magazine, Thought Catalog, Elite Daily, News.com.au, and The Good Men Project. Mark’s dating videos have received over 60 million views, and his book “Make Him Yours – Beating the Odds of Modern Dating” was a best-seller on Amazon on its release.

Mark Rosenfeld

Dating & Relationship Coach

Expert Answer

A lot of subtle flirting involves communicating sexual interest without actually speaking it, like through touch or subtle innuendos.