How To Ask A Waitress Out And Get Her Number Without Overstepping

That waitress might just be friendly. But you'll never really know until you learn how to ask a waitress out properly.

It’s time you learn how to ask a waitress out the right and proper way. We have all see the guy who assumes the waitress is interested because she’s paying attention to him, you don’t want to be that guy!

I’m sure you’ve had many occasions where you go to a restaurant, cafe, or similar place and the waitress who’s serving you there is really attractive. You want to get her number and ask her out, but don’t want the whole thing to become weird.

That’s awesome and you’re more than welcome to try. But you have to be aware of a few things first if you want to do it successfully and without making a mess of things.

How to ask a waitress out – Don’t confuse simple friendliness with flirting

Before I say anything else, I have to mention that you should try your best not to confuse her professional friendliness with flirting.

So many guys make this mistake that it’s not even funny anymore. They confuse common courtesy and friendliness for flirting, then ask the waitress out and get rejected hard. Then the whole situation becomes immensely awkward and no longer fun for everyone involved.

The problem isn’t that you shouldn’t ask out women who are being overly friendly with you. On the contrary, if you’re single, then you should definitely take an opportunity to chat up and ask a woman out when she’s being like that.

That said, waitress and other service personnel are a completely different story. They are being paid to be very friendly with you. That’s their job and the basis of customer satisfaction.

In fact, most of the time when a waitress is being overly friendly with you, it’s because she wants to get a good tip.

That’s why it’s important you look out for this crucial difference between such type of friendliness and genuine flirting. Because it’ll save you a lot of heartache and frustration. And also prevents some intensely awkward and embarrassing moments.

I’d even go so far as to say that when you’re in the presence of an attractive waitress, you should always assume she’s being friendly because it’s her job. And not because she wants to sleep with you.

The process of asking a waitress out

With that out of the way, the main point of how to ask a waitress out the right way lies in your ability to engage in small talk with her. Small talk that eventually helps her see you not as a customer but as just a guy she’s talking to. In order to truly figure out if she’d be interested in you or if she’s just doing her job and wouldn’t want anything else from you.

Let me explain this in detail because this is vitally important if you regularly want to ask out attractive waitresses successfully.

Here’s the basic gist for asking out waitresses:

  1. Order your stuff
  2. Transition to regular small talk about nothing in particular
  3. Throw in some light flirting and teasing
  4. Watch her reaction and act accordingly

Now it’s time to explain everything in detail.

An important point when talking to waitresses

First of all, for the love of all that’s decent, do not try and transition into small talk and flirting if she’s very obviously busy and in a rush.

This is an asshole thing to do and can very likely result in her hating you. Or even losing her job if her boss sees her not working and instead chatting with you.

That’s why you should only hit on waitresses when the place isn’t busy and when you know she won’t get into any trouble. Because the last thing that’s on a woman’s mind in the middle of a dinner rush is finding a potential lover.

An in-depth look at the whole process

So here’s exactly how to ask a waitress out the right way and how I do it with great success. Mind you, it’s not a fool-proof plan because sometimes no matter what you do and no matter who you are, people just aren’t going to be into you. But it gets the job done and works quite well very often.

First, you get the business part over with. You focus on ordering whatever it is you wanted and let her do her job.

Then, you try to transition into small talk with her. You NEVER ask for her number or ask her out directly because 9 times out of 10 you’ll get a hard “No.” Unless you’re just her type and she’s been eyeing you all this time in an obvious way.

You can transition into small talk right away after you make your order if you notice her linger a little bit. But don’t do it if after taking your order, she rushes off somewhere. In that case, save it for when she brings you your things.

How you transition into small talk is entirely up to you. You can go with the tried and true “So hey, what’s it like working here?” and similar questions. I often make an observation akin to something like “There’s not a lot of people here right now. So what do you do for fun here when it’s not so busy here?” and similar things.

Small talk is important

When she answers, you can proceed talking about whatever you like. About the city you’re in, how long she’s been working there, about music, sports, pets and animals — it doesn’t matter. Just regular, normal small talk.

Elaborate on her answers to your questions, expand those topics and you’ll never run out of things to say.

The point is to get her to linger at your table and eventually talk about something unrelated to her work and to you as a customer. Basically, you want to screen her if she’d be willing to talk to you like a person to a person and not to a client who she’s serving.

This conversation doesn’t need to happen all at once. She can come back and forth to your table multiple times. As long as she’s engaged and eager to continue talking with you.

So, if you see she’s not very keen on staying at your table and doesn’t really want to talk to you about stuff unrelated to your current business predicament, then you’ll have a very clear sign that she wouldn’t be otherwise interested in you. If that’s the case, you can safely drop the whole thing because asking her out would be pointless. There’s nothing you can do about that because she’s simply not interested in making friends or meeting someone new.

If, however, you see that she has no problem staying and chatting with you about whatever, then you proceed to the next step.

Begin flirting after she sticks around

If you notice she’s been enjoying your company thus far, you should begin flirting with her lightly.

If she’s stuck around, then she’s obviously up for meeting new people. Because it’s obvious she’d rather stay and talk with you than go do something else.

So now’s the perfect moment to show her who you really are and showcase your wonderful personality. Flirt away, tease her, get her laughing, tell her funny, exciting or interesting stories. Get her emotionally invested in your short conversation and as a result, emotionally invested in you.

She has to want to stay and have fun with you, so make sure to give her a good reason by being fun to be with.

From small talk to getting her digits

Lastly, if you see that she’s having fun with you and your flirting is going well, ask her out!

Say something like “Hey, it’s been great talking with you and I’m actually surprised I’d meet someone as fun as you in such a way. I have to go soon but I’d like to see you again and continue our conversation when you’re not busy working. How about we exchange numbers?”

The exact words you say here don’t matter. As long as you let her know you’ve had a wonderful time with her, find her interesting and attractive and want to meet her again.

If she’s had a great time as well, she’ll very likely give you her number and go out with you.

That said, most waitresses are never allowed to have their phones on them while working. Or they may not even be allowed to flirt with customers and ask them out.

To remedy this, I usually just pull out my phone and say something like “Let’s pretend I’m looking something up so your boss doesn’t get suspicious. But tell me your number real quick and I’ll punch it in and then message you later so you get mine.”

You see, there’s nothing complicated in any of this. It’s a great way of practicing how to ask a waitress out because it lets you screen the ones who are interested in you from those who aren’t.

This method is perfect for beginners and people who are afraid of rejection. Since you essentially avoid being rejected at all if you do it the right way.

Out of all the ways I’ve tried asking waitresses out, this is, by far, the one which gets me the best results consistently.

Don’t make it weird, make it fun instead!

There’s one more thing you should know if you want to ask out waitresses and people who are working.

Don’t just barrage them with questions like you’re interviewing them. They’re working in that moment and the last thing they need is to enter into a pointless and boring conversation.

However, if you can inject some fun into their workday, you’ll make their time fly. They’ll remember you fondly because you made an otherwise unremarkable day into something better.

That’s why you should focus on making the whole experience as fun, exciting or interesting for them as you possibly can. This’ll make everything easier and they’ll be much more inclined to later give you their number.

Make them forget about their work even briefly and you’ll make their day.

Also, what makes this way of asking out waitresses particularly good for beginners is that it lets you avoid rejection by screening them first. If you see they’re not interested in staying at your table at all and talking about other stuff than their work, then you can let things go.

Plus, this lets you practice your social skills and helps you learn how to engage in small talk with people. That’s a very useful skill to have in life in general.

So, next time you see an attractive waitress, don’t hesitate to chit chat with her. See if she wants to stick around. Then flirt with her and eventually ask her out. Things can only get better from there.


As you can see, there’s a way to ask out a waitress that works very well a lot of the time.

With some practice, you’ll be able to get phone numbers from many different waitresses. You can even use this method to meet women who are working various other jobs.

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