How do I ask out a woman who’s not in the same league as me?


And I really mean she’s not in the same league. Let’s just say she’s making over $100.000 yearly while I don’t make half of that. I know I shouldn’t, but this makes me feel intimidated by her. She’s smart, beautiful, she can even handle herself in a fight (seen it) and she barely knows me. I’m not sure if this can ever work but there’s something inside me that keeps pushing me to try. I just don’t know how to do it. I don’t know her phone number, no Facebook, just know her first name. The only way to learn her name is to go to her workplace and somehow find out. That’s also scary to do (I’m not a very extroverted guy).


  • 7 Comments sorted by Votes Date Added
  • Tom

    I would personally send her flowers at the office. Send her a bouquet each week. Also leave a note with the flowers. Start off with “an admirer” and then (maybe in week 3) say this:

    “You probably don’t remember me (or know me) but I think you are a wonderful person and would like to get to know you more. Would you allow me the pleasure of going on a date with me? Nothing fancy and if it doesn’t work out I won’t bother you again.

    If yes, please leave a message at this number or just give me a call. I’ll call back.

    PS: I’ll keep sending you flowers until you do :)

    Hope this helps you! 

  • Robert

    Don’t be intimidated because you know what: most men feel the same way about her. Because of her position, not many men will actually approach her so you have a lot less competition than you may think. You need to start getting close to her even if you have to bribe a few people :). You can’t just call her out of the blue like that. Just make sure you meet her (maybe deliver something to her office) a few times and make sure she remembers your face. You want to be someone she knows (even if just a little) before asking her out. 

  • Merry

    I think you should just go for it! Who cares if she makes more money than you? Lots of women make more money than their boyfriends or husbands. And so what? And so what if you’re an introvert? If she is like you say she is: sure of herself, she may enjoy your company. You just have to stop wondering what if and just get out there and get her phone number and call her. Ask her on a date. If she says no then send her flowers and ask her again. Do this a few times and if she’s really not interested she will probably end up hitting you :) – not joking here but you need to take that risk because what if she likes you? 

  • mike459

    Step 1 – get her phone number or Facebook handle.

    Step 2 – Call her or send her a message saying this:

    “You may not know me but I do and I think you’re just great. I’m not a stalker, I’m just a regular guy who would like to get to know you better. If you’d give me a chance and have a date with me, I will do anything you’d like me to do for this to happen (I could carry your handbag for a month :) – anything you’d like.

    Have a wonderful day!”

    The best way is to do and not waste time planning and acting like a stalker. Try to use humor a lot as this will increase your chances. Also make sure she isn’t married or in a relationship before doing this. Good luck!

  • Lucia

    While I partially agree with Robert, I think that you should just write down what you want to say and just call her. Tell her that you think she’s amazing and you would like a chance to meet her. Don’t take no for an answer but don’t be an idiot either. If she initially says no, just send her some flowers and call back. Tell her you’re not a stalker, you’re just someone who wants to get a chance. Don’t give up until she agrees to go on a date. Don’t push it if she has a boyfriend. Only try seeing her if she is available. 

  • ryan_riolu
    I gotta agree with Tom here. Smart, beautiful girls would get 1000s of texts and how many do you think they'd reply to? Maybe 10, or even less. 

    Flowers and chocolates all the way
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