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How to Ask Out Waitresses and Bartenders

by Ron Louis & David Copeland

Question:  There's a real cute girl at my coffee shop, and I want to ask her out. She's so hot I can't believe it, and she's always really nice to me. But I don't know if she's really liking me, or just paid to be nice. So I'm scared to ask her out – I don't want it to be awkward. Is there any way I can make it easier?


Answer:  Ah, the lure of the barista. Girls who work in coffee shops, or other women who are paid to be nice, pretty, and helpful, catch the eye of any man. And why not?

There are three things to keep in mind as you attempt to seduce women in service jobs that will make it easier for you to take action and to ask her out...

Make It Easy and Not-Awkward For Her to Say No to You

...if that is what she wants.

Why? Because you are currently so afraid it will be awkward if she wants to say no, that you don't ask her out at all.

You have reason to be afraid it might get awkward. When you are asking out a woman in a service job, several power differentials come into play.

While it seems to you that she, as a hot woman, has all the power in the interaction, it probably seems to her, as the employee talking to the customer, that you have the power. You could cause her trouble, harass her at work, or even cost her her job if she says no to going out with you.

Therefore, it's risky for her to be honest. To her, you have the power, and when you ask her out, you put her in a potentially awkward situation if she wants to say no. You sense this, and it makes you not want to ask her out. Therefore, if you can remove the potential awkwardness, it'll be easier to ask her out. Here are some ways to do that:

1) Ask her if she has a boyfriend.

You might say, "You seem like an interesting woman. If you don't have a boyfriend, I'd like to ask you out." This allows her to respond that she does have a boyfriend, even if she doesn't. It saves face for both of you and doesn't disrupt the customer/barista relationship. She doesn't have to say she doesn't want you – she can blame it on the boyfriend. Knowing she has this "out," it will be easier for you to get up the nerve ask her out, and possibly to get a "yes."

2) Ask her if she's allowed to date customers.

You might say, "You seem like an interesting woman. Are you allowed to date customers?" This allows her to blame her workplace, rather than having to say she doesn't want you. Once again, knowing that you are taking her out of her bind, it'll be easier for you to take action.

3) Ask her if she has a policy about dating customers.

You might say, "Do you let yourself date customers? I know some women don't," and see what she says. If she doesn't want to go out with you, she'll be able to blame her policy, rather than rejecting you directly. You've released the pressure in the situation, and can move forward.

Make It Okay, Whatever Happens

If you go to this coffee shop or restaurant a lot, you may be stopping yourself from taking action by fantasizing about how awkward things will be there, for the rest of time, if she says no.

You can overcome this by committing yourself to being a source of certainty, with this woman, that everything is okay, no matter how she responds to your invitation. You do NOT wait for her to be okay with it; you demonstrate that everything is okay, and she will feel that way, too.

Knowing you are committed to it being okay, no matter what happens, will also help empower you to ask her out.

As Is So Often the Case, It's a Numbers Game

In our experience, when a man has no other ways of meeting women, he tends to get fixated on a coffee shop girl, or on a waitress. He also tends to lose perspective, becoming especially unable to tell if her friendliness is the result of her job description, or a result of her attraction to him.

If you want to have a better sense of whether or not the hot coffee-shop girl likes you, keep your perspective clear by having other women in your system. Explore niches, do online dating, have a social life, say yes to invitations, and so forth.

If you need help with that, check out the free lessons from the Mastery Program, at howtosucceedwithwomen.com.

Best of luck!

About the Author: Ron and David are dating coaches. Their book How to Succeed With Women has sold over 40,000 copies. They have been featured in magazines such as Cosmopolitan, Playboy, YM, Maxim, GQ UK, Swank, Gallery, and Players. They have also been on the Rosanne Barr Show, the Issac Hays show, To Tell the Truth, Fox News, CNN, UPN, and ABC. For more great tips on meeting and dating women or to ask a question go to howtosucceedwithwomen.com.