If you are looking to tell a coworker that you are interested, it is a good idea to tread lightly. Because of all of the issues surrounding relationships in the workplace, you want to make sure that you approach this in a delicate manner and don't cross any lines. The best way to do this is to come up with a plan before you make any kind of move.
- Decide whether or not this person is worth the attempt. Because of the sensitive nature of dating someone in the workplace, you want to make sure that you are really interested in this person and not just looking for a fling. Remember that throughout the process, you may run into consequences.
- Think about what you want to say, before you say it. Have an idea in mind about how you would like to tell this coworker that you are interested. One of the best ways is just to have a face to face conversation. This way, you can see if she feels the same way, or if it is something that you should just drop. If you just wing it, something you say might be misunderstood and can end up being a problem
- Have the discussion with the coworker you are interest in privately. Obviously, this isn't something that you want to shout from the rooftops, nor so you want other coworkers involved. However, you also don't want to have this conversation in a place that the other person might feel uncomfortable. You can have the conversation in a crowded break room provided that you are discreet.
- Bring up the subject casually and in a round about way. If you put out a few comments, you may get a sense of whether or not this person is interested in their coworker: you. If you sense that things aren't going well and there is a lack of interest there, abort the mission.
- Keep it light. Suggesting that you get two get together for drinks or a movie is a great idea. No pressure and a good time are a great combination.
- Take rejection well. If it doesn't work out, you don't want to make a big deal about it and draw attention to the situation. Just let it go and realize that there are plenty of other fish in the sea. Also, make sure that all of your interactions with the coworker that you were interested in stay the same. Try to keep things from being awkward and do you best to just act as though nothing happened.
- In the same way, if you find that your coworker is interested, don't make too big of a deal about it. If things get serious, it may be necessary to let other people know about what is taking place, but at this point, just enjoy it and keep it to yourself.