I got a question on Instagram about this – is it okay to hit on a girl when she's working?

In other words…

Can you check her out in the checkout line?

Can you ask for a tall cappuccino, and her number?

Can you ask her out, when she drops off the check?

It’s a common question, because there are often beautiful women working in the service industry.

And a lot of guys start off this way, to build up some confidence, and to get used to talking to women. My own mastermind group suggested I do the same, when they were filming me doing some approaching and I was getting a little nervous (yea, it happens to me too!).

But I resisted, because I’ve never liked it. First off, it feels icky.

How can I be sure I’m not that creepy guy that she is obligated to talk to, because she’s not supposed to ignore customers?

And secondly, even if it does go seemingly well, it just doesn’t feel…genuine.

How do I know that she actually likes me, and that she’s not just doing her job of being friendly?

Because I’m not looking only for her attention, or her phone number, or her body. I’m approaching her in search of a genuine connection (through which I will receive her attention, phone number, and body).

So I don’t even start off my clients this way. I make them approach women who are not working, because in that case, women have zero obligation to talk to you. That’s where the rubber meets the road, because all you have are your skills. It’s incredibly difficult to do and you will get rejected a lot, but it’s the fastest way to learn and grow your confidence with women.

Butttt…I have to be fair. Have I ever asked a girl out who was working? Definitely. So that begs the question – when is it OK?

And here’s what I’ve decided – it’s okay, so long as you’ve also been approaching plenty of women who are not working.

Because you don't want women who are working to become a crutch that you rely on. You don’t want to get to the place where if you don’t have a “reason” to talk to her, you just don’t approach her.

Because that’s being a coward, and that’s where most guys are, including my former self. And here’s the most significant realization I had, which got me out of that place – it doesn’t matter if I have a good reason, or even if I say things with the perfect tonality, or if I come across awkward, or if I get rejected – all that matters is did I try?

Did I stop her?

Did I get her attention?

Did I put myself out there and get those specific words (“hey, you’re super cute, and I had to come say hi”) out of my mouth?

The more I did that, the more confidence I built, and the more comfortable I became with women – and the better I was able to read social cues and know whether or not the girl who is working is actually interested in me.

So yes, go ahead, chat up that beautiful barista. But only if you had the courage to first chat up that cutie who is standing in line in front of you (and probably wearing those tight, body hugging yoga pants).

Damn those yoga pants.

Regardless, you should always be friendly and nice to people that serve you. Tip them well, call them by name, and just be pleasant. Because they often deal with high expectations and unappreciative customers. Don't go Larry David and overdo it, just be polite, that's all that's needed.