Article: 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.   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. 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.  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. 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.  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. 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.  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. 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.  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. 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.  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. 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. Nothing will turn off a potential work crush more than if she gets the idea you’re disingenuous. 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.  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.
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Initiate casual chat through email, instant messaging, or when you see her around the office. Be all ears. Before you make your latte run, ask if you can bring her back a coffee. Ask her for advice or help on a project you’re working on. Walk her out. Initiate an office happy hour. Pursue a flirtation with one only co-worker at a time. Be conspicuous and keep your flirting sessions under wraps.