How To Pick Up A Waitress – Flirting With Women

She greets you with a huge smile and a wink every week. Only problem is, it’s when you’re ordering your morning coffee.

I get tons of emails from guys just like you asking if it is possible to flirt with a girl while she’s at work.

Even if you’re normally great at flirting with women, you may find it impossible to say the right thing, or even be sure if it’s right to say anything, the second she steps behind the bar and the girl you want to ask out is at work.

I can totally understand that: you don’t want to bother her and, having been a waitress myself in the past, I can confirm that it does get tiring getting the wrong kind of male attention when you’re in the service industry.

I’m not going to lie: attractive waitresses, barmaids and other women in customer service based industries are going to get hit on a lot. When I worked as a waitress after one too many tired lines or routines I did find myself thinking, ‘Oh boy, not another one,’ then smiling politely and walking off. I didn’t like feeling like an object when I was at work so I would let any crude comments or obvious lines drift in one ear and out of the other.

There were two kinds of guys I encountered all the time when I was working:

1. The ones who were super nice to me, who I secretly  knew wanted me but were too afraid to ask me out

2. The jerks who saw me as an achievement and a goal of “getting the waitress” so they tried to show off in front of me, use lines on me in front of their buddies and generally treated me like a “thing” instead of a person

You don’t want to be the guy who uses a line because he wants the prestige of getting the hot waitress’s number, but you also don’t want to be the guy who is too afraid to ask.

So how do you ask out a waitress so that you don’t seem like just another patron?

Follow these rules and you will be all good:

#1 – Talk about things other than typical “bar or restaurant stuff”. So no hour long discussions about Jack Daniels or where Vodka comes from.  Think bigger and don’t be afraid to share about you rather than trying to fit into her life.

#2 – Don’t wait for the perfect moment to ask her out. I used to have guys stay till the wee hours of the night thinking “great she’s off work, she’s totally accept my invite for a date now”. Not true.  I hated it when I could tell guys were just hanging around waiting to ask me out. Felt creepy.  If you want to ask a waitress out, then ASK HER OUT right then and there. Then continue on with your night.

#3 – Remember that work sucks and nobody wants to talk about their job. Do you want to talk about engineering? Law or working at Best Buy? Hell no.  Talk to her about her life outside the bar and show her that you can see past her little apron.

#4 – Make sure you treat her like a lady. Just because you are paying her for a service, doesn’t mean everything is included 😉

So next time you are at a bar, restaurant or even a clothing store and see a hot girl working there, approach her, strike up conversation and don’t be afraid to ask her out.

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  1. ron // November 28, 2011 at 5:42 pm

    this was a good topic to blog about and what guy hasnt been attracted to the cute waitress/bartender but you left out a couple of things…do you ask her out before or after you leave the tip…if you ask her out before you leave the tip she will probably leave her phone number to get a very generous tip and that number probably doesnt go anywhere…these girls arent stupid…ok then you leave a very generous tip…she sees it…and then you ask her out…it then looks like you’re trying to buy her…too small of a tip and you look cheap…remember these girls are getting asked out all the time

    • Marni Wing Girl // December 3, 2011 at 7:01 pm

      You should ask for her number when you feel like you’ve made an emotional connection with her: this could be before or after the tip. Instead of focusing on the money and transaction focus on whether she’s smiling, comfortable and whether you’v got a genuine connection with her 🙂

  2. christofer // November 28, 2011 at 6:05 pm

    A waitress will smile and seem receptive
    when you flirt with her (assuming that
    you’re not vulgar in your approach).

    You will feel like you’re getting some
    where & making some sort of connection
    because that’s what she wants you to
    believe;by doing this she’s hoping to
    get a larger tip.

    Waitressing 101

    This is all moot,if you are wealthy or
    extremely attractive;then,you may have
    a chance.

    • Marni Wing Girl // December 3, 2011 at 6:59 pm

      I actually think it’s not so much about you, but about your ability to connect with her: and that has nothing to do with looks or money 🙂

      • don // January 25, 2012 at 9:27 pm

        Hi Marni,

        I’m in a situation where i’ve kinda connected with the bartender and I’ve gotten her number. We’ve text back and forth for a few days now. I really don’t know how to make it clear that i just dont want to be a friend. she’s not giving me the friendzone treatment yet but I guess I’m lost on what to do to make sure she knows my intentions and I dont get into the friend zone

        • Marni Wing Girl // January 30, 2012 at 1:56 am

          Hey Don

          I think you need to be direct and open here and tell her that you’d like to take her out for coffee. Take action, and don’t end up in the friend zone 🙂

  3. Kevin // November 28, 2011 at 7:34 pm

    I like asking women at work this “What do you do when you aren’t working” If she has a boyfriend, she’ll tell you right then and there like “usually go out with my boyfriend” You’re basically seeing if she’s single in a very indirect way while still being interested in her.

  4. skw // November 28, 2011 at 8:05 pm

    A couple of other conditions have to be in place here:

    -she can’t be too busy
    -she can’t be too NOT busy either, if you’re the only guy in there on a slow night, that’s a reflection on you

    • Marni Wing Girl // December 3, 2011 at 6:58 pm

      Definitely not a good idea to try to hold a big conversation with a waitress whilst she’s at work. Be respectful of her job, and try to speak to her briefly on several occasions, rather than one long interaction and you should stand a better chance of getting her number 🙂

  5. george // November 29, 2011 at 10:09 am

    I don’t understand why but I was hover by a lovely waitress while I was talking with my group at the table not paying her much attention. She would pass by saying, “More water?” or “More coffee?” I felt that she was trying to get my attention.

    The second time I went that restaurant she was more sociable until I ask her email. Then she went cold. The third time we went there she didn’t serve us. But while she was talking to us she was very friendly.

    If I remember, I had told her, “I want to keep in touch with you. Give me your email” then she flaked out. “I don’t give my email to strangers. Why don’t you come a few more times and I would get to know you and only then maybe I’ll give”. But after a while the restaurant closed down. I think she was the owner’s daughter.

    • Marni Wing Girl // December 3, 2011 at 6:57 pm

      Hey George

      It sounds to me like on this occasion she was just being a diligent waitress: it can be tough to read a woman’s signs correctly so I’ll have to put a blog together on this.

      I think in that instance it would have been great for you to take the lead and be accepting of what her concerns might be. If she doesn’t give out her contact details striaght away take the initiative to let her know that’s fine, and make a mental note that you need to get to know her betterm make her feel more at ease in your company, and then be ok to try again.

      Good luck 🙂

  6. smooth // November 29, 2011 at 1:00 pm

    If a girl says I have a boyfriend straight off the bat, then she is onto you.
    I once read it takes up to 8 hours to get to know someone, You have to get to know her a little better. Break down those walls and get inside her mind and let her see the good person in you. You are not one of the jerks that normally cracks onto her, but you are also not one of the “good guys”

    • Marni Wing Girl // December 3, 2011 at 6:53 pm

      Hey Dave,

      I actually think it’s ok for a woman to know that you’re flirting with her: in fact being direct and honest and real is great.

      If she says that she has a boyfriend straight away though you have to make a judgement call: if you think she’s being sincere you can leave that one, and know there are a lot of great single women out there. Or you can think that the ‘boyfriend’ is just a knee jerk reaction to her feeling a little pressurised, you can take feedback from that, adopt a slightly different approach, and think that you can either turn this around and get a date, or a great friend, from the interaction.

      Good luck 🙂

  7. cain // November 29, 2011 at 4:33 pm

    Uh yeah this chick from retails… was very nice to me… she tool me out… i treated her like a lady… she paid… she bought me a beer… took me to her house… and you get the picture….

    • Marni Wing Girl // December 3, 2011 at 6:53 pm

      Glad to hear that you’ve had some great experiences dating Cain 🙂

    • Victor Aziaka // December 5, 2011 at 11:33 pm

      Howd all that happen i wanna know

  8. christofer // November 29, 2011 at 5:51 pm

    The interest a waitress or any other
    woman in the service industry shows
    you is not genuine.When she appears
    to be interested,laughing & smiling
    a lot she is WORKING.Specifically,
    working for a bigger tip….and
    hopefully repeat business & more

    Only celebrities,the wealthy and
    extremely attractive guys or those
    with exemplary “game” have any sort
    of chance.

    • Marni Wing Girl // December 3, 2011 at 6:45 pm

      Hey Christofer,

      I actually agree with a lot of the qualities that women think are attractive: assertiveness, confidence etc. Although there are definitely better ways to show it as a man than just being a jerk. I love it when a guy is able to be masculine enough to lead me and take that attractice role, without knowing he’s a player. In fact that’s the nicest feeling.

      As for waitresses I know generally they are working, and you definitely have to account for that. However if you distinguish yourself from normal ‘customers’ and connect to her as a human being, rather than just ‘the hot waitress’ you will set yourself apart and be able to date her. This won’t work with everyone, but I know lots of women who have gone on dates with guys they met whilst they were working. Women love to be asked out in whatever context, as long as it is done sensitively and congruently.

      Thanks again for your comments

      Marni 🙂

  9. Fred // November 30, 2011 at 5:30 am

    Hi Marni,

    What should I do with a girl I like who works at a fast-food?
    I go there often and I can sense that she recognises me.
    Sometimes she smiles at me outside of a transaction such as when she’s cleaning a table or something. Does it mean something?
    When I order I always look deep into her eyes but so far that is as bold as I get.

  10. Eric // December 5, 2011 at 4:34 pm

    Marni, you and I have actually discussed this, whether or not you remember 😉 Guys, it just takes being sincere, and it may take time. But you don’t have to be wealthy, famous or any of that. Just be the man you know you are. Take my word for it. And stay out of the friend zone!

    • Marni Wing Girl // December 16, 2011 at 8:58 am

      Hey Eric

      Ditto that on your comments. Keep ’em coming

      Marni 🙂

  11. Victor Aziaka // December 5, 2011 at 11:35 pm

    How do u get her to be curious enough to come talk to u

    • Marni Wing Girl // December 16, 2011 at 9:07 am

      Hey Victor

      Unfortunately a lot of the time women will give you all the signals but will expect you to approach.

      So next time you’re thinking about how you can make her come to you, do the masculine and direct thing by going over to her.


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  13. Guest // July 23, 2012 at 11:15 pm

    Hey marni,

    My name is dan and id really want to have your advice on something. I went to this restaurant closeby. I usually go to this restaurant when eating dinner outside the house. There is this really cute and nice waitress there, and I really want o try and go for her, and see where i get. She is a bit older than me though, I am only 17 and i figure she is aorund 19-20. And I know you will probably say that im too young, however I think i do have a pretty fair chance. Im pretty good looking (alot of my friends which are girls say so, and i think im good looking to 😛 ) but other than that I can interact with women fairly confidently.

    Anyway, id like to ask you a question, do you think I would stand a chance, and would you have any other tips? 🙂

    Thnx alot in advance 🙂

    • Marni Wing Girl // July 25, 2012 at 11:40 am

      Hey Dan

      I’d say to go for it: as you miss 100% of the shots you don’t take. You’re also relatively close in age, and confident with it. I wouldn’t bring up the age gap, just strike up a conversation, see if you connect and if it goes well take her number.

      One last thing you may want to consider though is if you can go back to this bar quite regularly it may be worth chatting to her over a few seperate occasions i.e. just start by saying hi and swapping names, then the next time you see her speak a little more, then when she’s got to know you a little ask for her number.

      Good luck

      Marni 🙂

  14. Guest Girl // April 9, 2013 at 5:45 am

    Hi, I’m a hot waitress. I get tips bigger than the actual orders and constantly hit on.

    But there was a cute older guy coming in with his friend once a week who would make me laugh. My coworkers would tease me over it and I could tell he wanted to ask me out. One night when it was really slow he came in alone but after that he stopped showing up.

    We had inside jokes and had begun to know about each others personal lives.

    He hasn’t been in for weeks and I’m wondering if maybe he gave up thinking he had no chance…?

    • Blew it // May 27, 2013 at 8:31 am

      You could have just asked him out yourself or tried to get something to keep in contact with him. He could just be busy and hasn’t had the time to eat out, if not and he really isn’t going to come back you might have just blew your chances.

    • Manfred Hideous // January 6, 2014 at 9:15 pm

      I know this post is seriously old but I found it while googling about something similar. I’m a regular at a live blues bar and one of the waitresses has me wondering if she likes me or just likes my tips… because I am there alone for hours, I pay for what I think she might have earned. I rent the table, if you will. Since I don’t drink much, the tip is 50% minimum but only because not having as much traffic cost her (though most people do what I do as well). I do this for all wait staff as my mom was single, poor, and raised my on tips.

      Anyway, this guy might be a bit like me. I know my waitress must be getting hit on a dozen times a day. Since I don’t want to be ‘that guy’ I keep to being friendly and not pushy. This older gent may just have been raised to be polite and he likely did give up after not getting a clear enough signal (many guys are really dense like that).

  15. Shiggity Shwa // May 2, 2014 at 9:21 pm

    nice article. will you go out with me? 😉

  16. Jupit // January 27, 2015 at 1:07 am

    I love talking about engineering