Tips for dating your boss

If you do tell them, it might make them more wary of your motivation — or they could be jealous if you get promoted or land a good gig.

How to Date Your Boss | HealthGuidance

There is no right or wrong here, but approach the water cooler chatter with caution. It can sometimes be hard to separate your work and personal relationships. Make sure they treat you that way. If you ever feel disrespected, talk about it. Or he spent a long time with your colleague discussing something? If you are seriously into your boss and think the romance could last the distance, it might be worth asking to move teams or looking for another role elsewhere.

This is also worth thinking about in case it all goes wrong and you split up, as this opens a whole new can of worms. This also prevents you from having the problem of spending too much time with your partner which can leave you with nothing to talk about potentially. Separate Business and Personal: Before you find a solution to your predicament you may well have to deal with your partner in a professional setting at some stage and they might have to reprimand you or you might need to go to them for help.

Think About it and Talk About it: In any relationship it is important to discuss the pros and cons with your partner and weigh up whether you are a viable couple and could work together in a long term relationship. When your career is on the line this is even more important so make sure to talk through your feelings and your concerns with your partner and to tackle problems together. At the same time think long and hard about how much you want this relationship and whether you are willing to sacrifice your job for it if necessary.


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Make sure that you really are attracted to the person and not just their position and the situation. Try a gentle, brief touch on the forearm or the shoulder when speaking with your boss.

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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. Pay attention to the signals.


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  • 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 her way to avoid you, you have likely made her uncomfortable and should abort your flirtations immediately. 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.

    Ask Wendy: Dating the Boss!

    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. Be honest and direct.

    How to Date Your Boss

    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.

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    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: Include your email address to get a message when this question is answered. Already answered Not a question Bad question Other. Article Info wikiHow is a wiki similar to Wikipedia, which means that many of our articles are written collaboratively.

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