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How to Ask a Girl Out

3 January 2009 12 Comments

Now, we’ve talked about everything from how you should act when you’re meeting your woman’s friends to how to avoid being hustled by women, but now it’s time to mention how you should go about asking a girl out on a date. This stuff comes naturally to some men, but a majority need a push in the right direction to let them know they’re doing it the right way. Before I mention the proper way of doing it, I wanted to mention the improper ways of doing it. Also, there’re many different scenarios and situations where men talk to or see beautiful women that they want to ask on a date but because of minor reasons here and there they don’t end up taking the plunge and don’t end up actually asking for their digits.


“Will you… Uhm”

We’re no longer in the sixth grade where you used to pass a note to a girl across the desk during class with “Will you go out with me?” scribbled in it. Some even went as far as supplying the girl with two check boxes marked ‘yes’ or ‘no’. That’s where the real mistake was. The man should not offer them a real choice to say no. In fact, you shouldn’t even view asking a girl on a date as a yes or no thing with any chance of rejection. “Will you go out with me?” is probably the worst way anyone could ask a girl on a date. It’s direct, it makes the girl feel like she’s right away in a relationship with you if she says yes, it puts the girl under the gun, and yet it gives the girl the idea that the ball is in her side of the court and she can play any which way she chooses.

And then as we got older, we tried lines like “Will you go out with me or something?” or “Can we go out sometime?” These were all just modifications of the same old line. So remember, you can’t be direct or concise with women when you’re asking them out. But you can’t make it seem like you just wanna get together with them as friends. You have to find that sweet centre. You have to make the girl think you’re sort of into her because of your humorous flirting, yet when you ask her for her number you should just say something like, “Here, let me get your number I’ll call you, we’ll get together sometime.”


You’re the Boss

The line I mentioned above really isn’t a question at all. It’s a statement telling the woman to give you her number and that you’ll call her sometime because you like how she carries/handles herself. You can add something like, “…we’ll get together for drinks sometime” or what you feel like, but make sure that you remember that you’re the boss and she’s lucky enough to qualify for a date. It’s a bit harder when you see the girl at a public place and haven’t started a conversation with her yet, but all that matters there is just the right approach to the girl and then once you’ve gotten the convo going and you feel like you’ve been talking long enough to feel some sort of vibe from her that she digs you and isn’t blowing you off, then go for the line to get her number. You don’t necessarily need to ask for her number at the end of your conversation, if you find a gap in your convo while she’s laughing at something you said it’s a good a time as any to pop the line in because at that moment you’ve said something truly funny and she sees that you’re a great, fun guy to go out with even just for drinks and so she’s vulnerable to give up those digits. And once you’ve got the digits, keep playing your game and one day when you’re free and have nothing better to do than go out and ‘waste’ your time and possible money on this girl, then go ahead and call her. Just make sure this isn’t the same night as the one you got her number on. It’s alright to call her the next day as long as it’s a weekend. If you got her number on a Wednesday, wait a bit and call her on Friday to set up a date for that Friday. And also, don’t call on Thursday to set up a date for Friday. Some guys like to plan things like that, but spontaneity is best in this case, I believe. Call her in the day time to set up a date for that same night. If she can’t get together than night, don’t seem desperate by asking her if she could come out tomorrow or the next day. If she says, how about tomorrow, then just tell her you could probably do that but you’ll call her tomorrow when you’re sure.


  • Kisha said:

    What? You mean we women aren’t in charge of anything?? LOL I like the asking if we want to get together sometime, that gives us plenty of options not something that is set in stone. Flexiblity is a good thing.

  • Carl said:

    Give no choice for the women—fucking love it!

  • Dan said:

    Nice addition to the series. You’ve got a lot of posts here, and they’re all pretty darn good. Soon you’ll be able to turn it into a book like The Game. I like your stuff better though, I must say. I like the experiences.

  • Nancy said:

    hahhaa I remember getting those notes during class with the checkboxes. lol fun stuff

  • casual love said:

    A very interesting post , Most boys have this draw back and well written and advised

  • Mark Ian said:

    I learned alot on the advices of this post. Thanks for sharing!

  • Jack Reed- How to approach Woman said:

    nice robby.. your articles are good..
    good job for that..

    you’ve shared your solid advice on people about this kind of topic

    very interesting and well appreciated..


  • John T Sullivan said:

    I really appriciate the advice!I’ve been married for a while! It good to get good advice o new tactics! Newly divorvced

  • Candy said:

    I totally agree – it doesn’t work for me when guys ask you out directly, especially if we’ve just a met a couple of times. It makes the situation awkward and at the same time, it signals the guy just wants something from you or he wants to know just a portion of your character that he finds interesting. You can actually know a girl more if you hang out with a group of friends instead of just a one-on-one date or encounter.

  • Robby G (author) said:

    @Candy: Thanks for your thoughts. I agree that being in a more relaxed environment with friends around, you definitely get a better, more honest, understanding of the girl. I remember hanging out with a girl I met at a club and one on one she was very cool and collected but in a group her honest self came out and I could tell we weren’t compatible. You really do learn a lot about someone when they’re in a relaxed environment, like for instance around their friends.

  • Henry James said:


    LAWYER- You know what this means, right?

    HANK MOODY- Yes. It’s obvious. I’m very good in bed?

    LL- That, and the prosecution has a lame case. And they know it too. Expect a deal imminently.

    HM- Ooh, I like it when you say “imminently.” It gets me a little hard.

    LL- Good to know.

    HM- Okay, well, we’ve got to celebrate.

    LL- Slow down. It’s a little early for candles and cake.

    HM- Well, I’ll be having dinner, you can do whatever you want. As long as it involves alcohol and bad decisions.

    LL- Sorry, I have a dinner tonight.

    HM- What’s his name?

    LL- Vanessa.

    HM- Vanessa?

    LL- Mm-hmm.

    HM- Sounds effeminate to me.

    LL- She is. She’s also my best friend.

    HM- Oh. Will you two be brushing each other’s hair at any point during the evening? Or perhaps gently massaging each other’s shoulders?

    LL- I see why you sleep with teenagers… You are one.

    HM- It’s true, I am kind of retarded. But I’m also kind of amazing.

    (Lady lawyer’s secretary enters the office.)

    SECRETARY- Okay, don’t forget you have a 12:00 with Randy and Gary. And then Lou needs to see you in his office.

    LL- All right.

    SECRETARY- And Jake called. And he needs to cancel dinner tonight. But he sends his love.

    HM- J’accuse!!

    LL- Thank you, Patti.

    HM- Thank you so much. Very enlightening.

    (Secretary leaves)

    HM-Now you HAVE to have dinner with me.

    LL- Why, because I adjusted the truth? I don’t owe you any sort of honesty about my personal life.

    HM- Fair enough. But you told me you were having dinner with a woman, which lead me to believe that you didn’t want me to know you were having dinner with a Jake. Who is probably very handsome, very fit, and very fuckin’ boring. Four minutes of mish, followed by a little oral to top you off… am I right? Done in time for Leno? No, you strike me as a Letterman gal… is that right?

    LL- And why would I mislead you like that?

    HM- Well, that’s obvious. Come on, you’re sweet on me.

    LL- Does this shit really work for you, Hank?

    HM- Not at all, not really. I’m just playing. Don’t be hating. I’m in a good mood because of you. I’m just trying to show my mucho appreciato in my own special way.

    LL- Yes, you are special, all right. Well, there is something we could discuss over dinner.

    HM- Yes, milady? Anything.

    LL- The issue of your bill.

    (Taken from Californication season 4)

  • Henry James said:

    I totally agree with your post, and this above here is a shining example of what you wrote. If you analyse the dialog, it matches exactly the Musts and Must NOT of the whole process of asking a girl out. Plus, he manages to survive multiple rejections in a row, only flipping them aroung to make his argument and wit stronger. Until she breaks, of course, mentioning the bill issue as both an acceptance of the invitation and an excuse to accept the invitation to have dinner with him.

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