Asking A Coworker Out & More

Yes, it's that time once again: The day we feature your dating and relationship questions. Although we would like to answer each one personally and with as much detail as possible.

The first thing to remember is that when you "ask a woman out," you immediately start a whole chain of mental and emotional events for a woman.


She has to decide if she "likes you" and if there could ever be anything between the two of you — and if she's thirsty and interested in free beer.

You get my drift.

Women know when you're asking them "out out." As in, you're asking them because you have a "romantic interest."

Guess what?

When you do this, it also puts the woman in the driver's seat in the situation because she instantly realizes that she has something you want. Have you ever heard of "wanting it tax?" It's when the price goes up the more you want it.

Now, as you probably know, I don't generally think that it's such a great idea to date women you work with because you never know what's going to happen, and the last thing you need is to lose your job or have to work for hours at a time in an uncomfortable situation.

And besides, attractive women usually have attractive friends, and if you're cool, the women you work with can lead to an endless supply of dates. Think it over.

You might want to think of it as a goose that lays golden eggs.

Even though I don't advise dating women you work with, I still want to address your basic question of asking a woman out without creating discomfort.

Remember, most guys do exactly the same things. They start talking to a woman then say: "Hey, can I take you out some time?" or "Do you have a boyfriend?"

This stuff is horrible.

It does exactly the wrong thing. It makes you look like a Wuss Boy who needs a girlfriend. And if she's not interested (which she probably won't be), then it will create some discomfort in the future.

Much better to test first, then take a small step.

If it's a woman you know, tease her, bust on her and generally act like you don't care. Make a comment about her and walk away. Be Cocky & Funny when you're with her, and don't be boring.

Then, if she's responding positively (laughing, hitting you, telling you that you're a pain, etc.), then say: "Hey, do you have e-mail?"


If she does, have her write it down, then say: "Bye."

From a man's perspective this might not seem any different than just asking a woman out.

But, from the woman's perspective it's very different.

First of all, you've never shown her any romantic interest, which doesn't give up your power in the situation and hand it all to her.

Secondly, instead of putting "dating" pressure on her, you've only asked her for her e-mail address (and maybe her number as well).

However, you haven't asked her on a date, you haven't created any kind of weird vibes in the air, and you have made her wonder what you have in mind.

It's powerful — think about it.