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Work can be a truly awesome place to meet a guy. You already see each other regularly, so it’s easy to get to know each other naturally. And by working together, you already have something in common and something to talk about. But turning a workplace crush into a relationship can also be tricky. If your boss or coworkers don’t approve, the road to romance could be rocky. However, once your crush likes you back, chances are he’ll happily do what it takes to make it work.

Part 1
Part 1 of 4:

Flirting at Work

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  1. Eye contact is fundamental to flirting and attraction. The eyes truly are the windows to the soul, so let him see yours. If you can’t look him in the eye, he’ll probably assume that you’re not interested in getting to know him. [1]
    • Though some eye contact is good, don’t hold his gaze for too long. There’s a fine line between looking and staring.
    • Generally, women show they’re attracted by lifting their eyebrows, making eye contact, tilting their heads down and to one side, and then looking away.
  2. This is possibly the easiest way to let a guy know you like him. When you smile at a guy, you appear open and friendly. That lets him know you’re approachable, and someone he can be himself with. [2]
    • The best smile is a genuine smile. People can read when a smile is fake, so just be natural!
    • If you've got great teeth or cute dimples, smiling helps show them off.
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  3. This isn’t always appropriate in the workplace, so be careful with this step. Some types of touch are commonplace in any environment, but some would feel uncomfortable in a workplace. There are three levels of flirtatious touch. [3]
    • A friendly touch happens in almost all working environments and can be a simple handshake or tap on the shoulder.
    • "Plausible deniability touch" is more personal and includes putting an arm around someone’s shoulder or giving them a hug. It could seem out of place in a fast-paced kitchen, but could come off as caring after a difficult office meeting.
    • Touching someone’s face is considered “going nuclear” in terms of touch. There are few work situations in which you’d likely touch a coworker’s face. However, if he has an eyelash on his cheek, that could be a perfect opportunity to gently and flirtatiously remove it for him. [4]
  4. Everyone likes a little flattery now an then. Point out something you like or appreciate about him. It’s best not to only focus on his appearance, though. Think of things he did that you thought were cool, or an accomplishment he’s proud of. [5]
    • Let him know you're always happy to see him. His personality makes the long days much more fun.
    • Compliment something he did well, such as giving aa great presentation or paying attention to detail. This will show you've been noticing him.
  5. Studies have shown that women are the most successful at flirting when they’re direct. If you’re not getting any response from your crush, it may be that he simply isn’t getting the message, and you need to be more obvious. [6]
    • Being direct has its limits. If you feel you’re sending all the right cues and not getting anything back, he may be trying to politely let you know he’s not interested.
    • If you fear this may be the case, just continue to be your usual charming self, and see if he is inspired to make a move himself.
    • You can be direct without being demanding. Say, "I'd love to get together sometime," instead of, "Will you get a drink with me?"
  6. Flirting via phone or social media can be either more discreet or more public, depending on how you do it. If you send a flirty text here or there, chances are no one else will find out. But nosy coworkers will notice if you’ve liked every one of his Facebook pictures. [7]
    • Always be extra careful when flirting digitally. For example, did you click “reply” or “reply all”?
    • Avoid anything that’s inappropriate for work. It’s okay to ask him out out for cocktails after a long work day. Sending suggestive pictures is not.
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Quiz

wikiHow Quiz: Does He Like Me?

Some guys can feel like a total mystery. How can you figure out if he likes you as just a friend—or if he wants something more? Take this quiz to find out!
1 of 15

When you two are in a room filled with other people, how often do you catch him staring at you?

Part 2
Part 2 of 4:

Presenting Your Best Self

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  1. There’s no one way to look great. Every woman has a different style, and every man has different tastes. Looking your best isn’t just about what he’ll think, it’s about wearing something that makes you feel confident. When you feel good about yourself, you automatically look more attractive to people. [8]
    • If you have to wear business attire to work, choose outfits that you feel great in. Wear that skirt suit that you know shows off your best features.
    • If your job requires that you wear a uniform, make sure it fits you well and is clean. And pay extra attention to the aspects of your appearance that you can personalize-- like your hair, nails, makeup, and jewelry.
    • If your clothes get dirty due to your work environment, choose clothing and hairstyles that make you feel confident and good about yourself.
  2. Good looks aren't always enough to get the guy. In fact, poor hygiene can be a major turn-off. Take at least one shower per day, and brush your teeth at least twice per day. Wear deodorant and clean clothes.
    • For some guys, good hygiene is more important than looks. Take good care of yourself first; the good looks will come naturally after that.
    • People who take good care of themselves are attractive, because it shows that they take pride in their appearance.
  3. A good night's rest will not only ensure that you're alert and functional, but it'll also help you look and feel your best. If you don’t get enough rest, you’ll be groggy and not on your A-game when it comes to flirting. [9]
    • How much sleep you need will mostly come down to your personal needs. Most people need about 7 to 9 hours of sleep.
    • Signs of not getting enough rest include undereye shadows and undereye bags. If you get your rest though, these should go away!
  4. Smell is the sense that is most closely tied to our memories. It’s also linked to attraction. If your crush begins to associate you with a pleasant scent, you’ll have that extra biological mechanism on your side. [10]
    • This doesn't mean that you should load up on the perfume. In fact, soap and deodorant can get you a long way.
    • If you choose to wear perfume, pay attention to his reactions. If he leans in, it's good. If he leans back or wrinkles his nose, it's not good.
  5. This is sometimes called playing "hard to get." What it really means is that you show him that you’ve got a lot going on and aren’t dependent on a man to make you feel fulfilled.
    • Show that you know how to led an interesting life. You could say, "Have you ever been kayaking before? I'm going this weekend and am wondering what to pack."
    • Be comfortable eating lunch by yourself or with one or two friends. This shows that you value time alone and with people you care about.
  6. If he only sees you at work, he may not know about the other sides of your personality. Make it clear that you’re not strictly business-- in or out of the workplace.
    • Do something fun or silly at work. Maybe organize workplace Secret Santas for the holidays, or bring in a goofy wall calendar for the break room.
    • Invite your coworkers to do something fun after work. This will let him to see how you act around other people in a fun environment.
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Part 3
Part 3 of 4:

Interacting Outside of Work

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  1. This shows that you know how to have a great time, and can provide him with excitement. It’s easy to invite someone out for a drink or dinner, but the most memorable people are the ones who invite us to do something we’ve never done before. [11]
    • Don't get discouraged if he turns you down. You can simply say, "Well, if you'd ever like to go in the future, let me know. I'd really enjoy that." This keeps the door open and puts the ball in his court.
    • Make it something you’re excited about. If you’re afraid of heights, don't invite him to go ziplining just because it sounds cool.
  2. If you’re having lunch or hanging out right after work, you won’t be able to completely change your clothes. But you can make small, flirty changes. If you’re getting together on a day off, be sure to let your personal style shine, since you don’t have to dress for work. [12]
    • If you’re going straight from work, consider letting your hair down after having it up all day.
    • If you’re taking your lunch together, you could leave the jacket of your skirt suit at the office to show a less formal side of yourself.
    • It’s okay to change your clothes between work and happy hour. If your clothes are dirty after a day of work, it makes sense to change before going out.
  3. If you’ve talked during the day, you can remind him of your connection by sending a short text or e-mail. Try to keep the conversation not focused on work, but instead on something you connected over. [13]
    • If he mentioned a band he likes, send a text that says, "Hey! I downloaded that album you mentioned. Thanks for the awesome recommendation."
    • Keep it brief. Even if he likes you, he may not want to be reminded of his workplace once he’s done for the day. Don’t expect long texts or e-mails.
  4. Make efforts to be friendly with the people you know he hangs out with. They don't need to know your intentions, but if they like you, they’re more likely to support a budding romance between you. [14]
    • If he’s friends with some of your coworkers, this one can be easy.
    • Remember, people tend to value their friends’ opinions, especially when it comes to relationships.
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Part 4
Part 4 of 4:

Maintaining Good Boundaries

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  1. Let him decide if he wants to have lunch near you, rather than always rushing to eat near him. If he works in another department, don’t spend too much time there or he might feel that you’re being intrusive.
    • You can send plenty of signals that you’re interested without crossing his boundaries.
    • Remember, no one wants to feel like they’re being sexually harassed at work. If they feel harassed, this could land you in trouble!
  2. Some workplaces actually prohibit employees from becoming romantically involved. Others have strict policies about the kind of communication that is allowable while on the clock. Don’t do anything to jeopardize either of your jobs. If it has to wait until after work, let it. [15]
    • Check the employee handbook. If you didn't get a copy, there might be one in the breakroom or office. It could also be available digitally.
  3. This can be the hardest part, but it’s almost bound to happen. No matter how subtle you both are, people are sure to notice what’s going on. Workplace gossip helps relieve the boredom of routine, so expect questions and rumors.
    • Gossip can work in your favor. If your crush wasn’t sure of your intentions, hearing a rumor might help him get the full picture.
    • Decide whether you want to dismiss rumors or be honest about your feelings. This can help you or backfire, so choose wisely.
    • Remember that the things you tell someone in confidence will likely make their way around the office eventually. [16]
  4. It’s very common for people to see workplace flirting as a way to get ahead in the company. First, you need to be honest with yourself that this is not what’s going on. Then let anyone who asks know that you would never engage in flirting simply to advance your career. [17]
    • This may not happen every time, but it is more likely if the guy has a higher position than you.
  5. With online dating apps, you can easily flirt with (and date) multiple guys at once, and no one has to know. At work, things are quite different. Even if your crush doesn’t realize that you’ve also been flirting with the guy in the mailroom, someone else will. And you can be sure it’ll get back to him. [18]
    • Seeing or hearing that you were flirting with another guy might make it seem like you aren't that serious or interested.
    • Not all guys get motivated by jealousy or competition. If he sees you with another guy, he may move on, especially if he had feelings for you.
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Expert Q&A

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Add New Question
  • Question
    Is dating a coworker a bad idea?
    Imad Jbara
    Dating Coach
    Imad Jbara is a Dating Coach for NYC Wingwoman LLC, a relationship coaching service based in New York City. 'NYC Wingwoman' offers matchmaking, wingwoman services, 1-on-1 Coaching, and intensive weekend bootcamps. Imad services 100+ clients, men and women, to improve their dating lives through authentic communication skills. He has a BA in Psychology from the University of Massachusetts Dartmouth.
    Dating Coach
    Expert Answer
    Be very careful if you're thinking of dating a coworker. If something doesn't go right, it can cause a lot of problems. That can create a toxic environment that affects your growth, how you work as an employee, and the energy you give off to everybody else. Plus, you might want to check with your HR department to make sure employees are allowed to date one another.
  • Question
    What are some tips for dating a coworker?
    Imad Jbara
    Dating Coach
    Imad Jbara is a Dating Coach for NYC Wingwoman LLC, a relationship coaching service based in New York City. 'NYC Wingwoman' offers matchmaking, wingwoman services, 1-on-1 Coaching, and intensive weekend bootcamps. Imad services 100+ clients, men and women, to improve their dating lives through authentic communication skills. He has a BA in Psychology from the University of Massachusetts Dartmouth.
    Dating Coach
    Expert Answer
    Create boundaries early in the relationship. Have a conversation where you establish rules at the beginning of the relationship. Don't compromise your career for a relationship that might not work out. Also, give each other space. If you can, try to arrange it so you can work in different departments or in different parts of the office. That way, you can both have a little space, even if you still work at the same company. This will make seeing them at work and outside the office more special for both of you.
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      Tips

      • Take it slow. Some people are very cautious about workplace romance. They worry that if things don’t work out, it could make for an uncomfortable working environment for a long time. If he doesn’t immediately ask you out, don’t get discouraged.
      • Make sure he’s single. Before wasting your time and efforts, do a little bit of recon. Casually ask a coworker if they know if he’s with anyone. Your coworker will probably understand your motives, so make sure it’s someone whom you trust.
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      Warnings

      • Workplace romance that goes bad can indeed create an uncomfortable situation. If you do end up going on a couple of dates with this guy, have an honest conversation about this. Agree that if things don’t work out, you both plan to still treat each other respectfully and be able to work together. If you both can’t agree to this, it’s not advisable to keep dating.
      • If things work out, be sure to talk about how open you’ll both be about your relationship at work. Depending on where you work, it may be best to keep the relationship a secret while on the job, or you may be able to be completely open about it. However, if you’re not on the same page, there can be painful misunderstandings.
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      About This Article

      Article Summary X

      Getting a guy at work to like you can have negative consequences, like disapproval from your boss or coworkers, so make sure you’re ready to deal with that kind of pressure. If you are, start by flirting with him in subtle ways, like holding his gaze for a few seconds and smiling. You should also compliment him, since everyone likes a bit of flattery. Try to focus on his personality or skills rather than his looks, which will make him feel valued as a person. If he seems receptive to your flirting, don’t be afraid to be direct about your feelings. However, if saying something like “Want to get a drink with me?” seems too direct, try a softer approach with something like “I’d love to hang out sometime.” For more advice, including how to plan your first date with your work crush, keep reading!

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