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5 Ways to Date a Woman in the Workplace

Approaching a woman who is a coworker must be done carefully

By David Wygant

As a dating coach, people come to my blog every day and ask me this question: ''David, there's this great woman that I want to date who works with me at the same company. How do I get her to date me and still keep my job?''

Dating in the workplace is very tricky, because you don't want to jeopardize your status in the company or her status in the company. You also don't want to create any bad blood between you and a fellow coworker if it doesn't work out.

Now, I'm not saying that this is something that can't work.

There are a lot of people who have fallen in love with coworkers... you just need to know how to approach it the right way, and how to "feel out" things as you do that, so you don't put either of you in a precarious situation.

Approaching a woman who is a coworker must be done somewhat differently (and more carefully) than approaching women with whom you don't work. With that in mind, here are my five steps to determine whether to (and, if so, how to) ask out your fellow coworker:

1. Start off by having lunch with her and a group of other people in the company cafeteria or the company lunch room. Get to know her in a group setting with no pressure at all. This way she gets to know you and what you're all about in a very casual way.

2. Get a group of coworkers together and go out for happy hour one day after work. Now that you've already had some time in the cafeteria to get to know this group of coworkers better (including the woman in whom you're interested), going to a happy hour with this group is a great way to get to know each other outside of the work environment. Being outside the work environment will also give you the opportunity to do a bit of flirting with her. This will be a good way to see if she's also flirting with you.

So the key to liking someone at work is not to let your coworkers know it. You want to be able to casually get to know each other so there's no pressure. During the happy hour, notice with which people she's hanging out more. Is she paying extra attention to you? Is she flirting with you? If so, then proceed to Number 3.

3. IM her one day and ask her what she's doing for lunch. Be playful and tell her that you really need to get out of the office, and that you couldn't think of anyone more fun with whom to have a lunch escape. Make it casual. You've already hung out with her in a group setting at lunch and at happy hour.

This is your chance to be alone with her, and to find out more about her. This is also her chance to get to know you better. Keep in mind, though, that this is not a date. It's just two coworkers having lunch. If this lunch is successful, then proceed to Number 4.

4. Start sending some emails to her during the day - just funny and light stuff. For instance, you could tell her about an office rumor you heard and say that you wanted to tell her about it first. You could also pass along a funny email that your friend forwarded to you. Tell her that you're forwarding it to her because you know she'd appreciate it.

Once again, keep it light and friendly. If she responds positively, you'll probably end up IM'ing with each other periodically during the day when you are both bored. If this stage is successful, then move on to Number 5... the close!

5. "The close." On a Wednesday or Thursday when you're speaking with her, casually find out what she's doing that Friday night. Tell her you are going out with a bunch of your guy friends, and that it would be great if she came with some of her girl friends so you could all hang out together. Once again, this is very casual... but it is also the final tell-tale sign you need to learn so that you can decide whether or not to ask her out on a date.

When you meet her group, start talking to her friends and watch what she does. If she keeps coming over, "claiming you," and trying to pull you away from her friends, then she is interested in dating you. If she ends up making out with one of your friends in the corner, then she'll never know about your secret crush and you will never have to worry about work-related issues or tension. If she's hanging out primarily with you (or even better hanging all over you and no one else), then it's time to confront her and ask her out on a real date.

You never know where you are going to find someone you like. There are no impossible situations. So the next time you find a woman in your office to whom you're attracted, follow these 5 easy steps so that you can see if she is also interested in you without worrying about what life at work will be like if she isn't. Explore the possibilities... you never know what may end up developing.