Do’s and Don’ts of Asking Someone Out!

I find dating and mating rituals of the human species fucking fascinating, don’t you?

I just shamelessly observe other people’s dating lives*. It’s daytime television, but in real life. What is my favorite thing to watch is how it takes FOREVER for people to take action upon liking someone.

Which I get. There are few things more terrifying than asking someone out. Especially if you really like them; you put yourself in a very vulnerable position. You’re basically saying “HEY – I’D DO YOU,” but less blunt . Second, it’s possible they don’t feel the same way (for whatever reason) That’s always shit. We want the people we like to like us back.

But, asking someone out is also really awesome. A) You teach yourself it’s good to ask for what you want B) you give someone else a huge compliment by showing them you think they are so doable lovely that you are willing to ask them out, and C) …they could say ‘yes’.

Now because of all of my slut dating LIFE experience, I figured out a few do’s and don’ts to keep in mind when you like someone and thinking of ‘pursuing them’ (in a non-restraining order kind of way).


  • Do not rush things like you’re some sort of Belieber Tween who’s spotted a Bieber look-a-like.** Dip your toes in the potential swimming pool before you dive in. Get to know the guy or girl in front of you first, beyond their great hair or their beautiful eyes.


  • Pay attention to how they respond to you. Now is the best time to keep your antennae out for social cues. Nothing you need a decoder or analysis team for, just the simple things. Eye contact, smiles, interest in your life, body language, stuff like that. See if it feels like there is something there.


  • Do not expect them to be THE ONE just because. It’s a strain on whatever you and this person might become, whether it’s just the casual date, short term fling, partner, great friends or eventual booty call potential. It’s best to keep all your fairytale fantasies on the shelf for the first bit.


  • Instead, just establish a connection with the person in front of you. That’s hard, I know — we tend to impose our romantic ideas and notions on the person in front of us, but instead just be genuine with the person in front of you. Be open, make jokes, make the other person feel good without any expectations and be selfless with them. It’s a good look.


  • When you do feel a click with this person and you decide you really want to get closer, don’t hatch an elaborate scheme for any of that. Don’t come up with a dumb ass reason to get someone’s number, don’t pretend to hang out somewhere you know they come all the time in the hopes you will see them, don’t get all complicated.


  • Keep it simple. How hard is it, really? “You want to have a drink after work?”, “Can I have your number?” or “I want to go see that movie, you wanna come?” Such short sentences should be able to be uttered with relative ease.
  • Be honest and clear, even in this first stage. You think he’s beautiful? Fucking tell him you think he’s beautiful! You would like to take him to your favorite sushi place? Fucking tell him and ask him if he wants to check it out with you! People underestimate how flattering it is to hear stuff like that. If you sincerely think or feel something positive about them, they deserve to know. They might take it to heart for the rest of their life, in a good way, even if your dating never goes anywhere.


  • When you’re not sure what’s going on in their head, when you can’t really figure out what is going on or when you haven’t heard from them in a while: Don’t freak out. Don’t spend your days checking your phone or e-mail, don’t start de- and reconstructing everything they do to find some sort of clue, basically: don’t get obsessive. Instead, focus on the other things you have going on in your life and trust that if you need to know something, they will tell you or the silence will eventually speak for itself.
  • DON’T get passive-agressive about it. No emails or texts with “Soooo….are you on a mission to outer space? You know, since you didn’t call? Jackass?” and no snippy behavior when you run into them. You are better than that.


  • Feel absolutely free to ask about what you want to know. “So, did you have a good time on our date?” and “You want to do it again sometime?” and possibly “Did I do something wrong?” when they don’t contact you. If you want to know something, never be afraid to ask.
  • Be honest about how you feel as well, no matter what the other party might think or feel. “I had a good time.” and “I think you’re awesome/doable.”  and “If you want to and are available, I’d love to see you again next weekend.” People seem to have this aversion against being vulnerable and honest, but I say ‘fuck it’. Life’s too short to play games. Even if you don’t get what you want, at least you are a sincere badass that saves time by being direct.
  • If things are going well, be considerate in terms of pace and affection. Be attentive to how the other person is feeling and how they like to proceed. Nothing wrong with knowing what you want, but it shouldn’t go against what the other person might want.

And that’s about all the opinions I have about that. I hope you have a happy love life, whether it’s single, dating here and there or a relationship, being happy is the most important thing — with or without another person.

*I’m sorry but if you’re going to either obnoxiously flirt or fight in public as a couple I have my fucking eye on you. Don’t like it, take it private.  

**I also find Beliebers very fascinating. 

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  1. Hihi, leuk artikel. Hoewel eigenlijk alles heel logisch is, is het daadwerkelijk ‘doen’ lastig. geef je ook een cursus hoe je die punten ook daadwerkelijk durft en kan toepassen? 😉 Ik weet ze, maar of ik het durf is een tweede! 🙂

  2. omg i could have written this post (only way less funny and witty, of course).

    “People seem to have this aversion against being vulnerable and honest, but I say ‘fuck it’. Life’s too short to play games. Even if you don’t get what you want, at least you are a sincere badass that saves time by being direct”

    is my motto. (alongside a few about chocolate).

    its like, im so over fucking games. ive actually never liked ’em. ive noticed sometimes a guy is put off by this and they confuse my honesty (het, i like you. wanna do something fun?) as either too straight forward or me being too available. and at first that could get to me and i would tone my ‘behavior’ down, acting more hard to get. but you know what? if you’re awesome and i like you, i am not hard to get at all, lol. i only come across as hard to get when i actually am, for that particular person (bc im ‘just not that into him’).

  3. Daten… Zal wel eens tijd worden, gezien mijn leeftijd. Maar ik denk dat niemand me ziet zitten, dus ik kijk niet eens meer om me heen. Hmm, je zet me wel aan het denken. 🙂

  4. The format of do then don’t then do is terrible for reading comprehension. Its hard to keep track of the meaning of the paragraph you’re reading this way.

  5. Omg, im a belieber. But in all seriousness i have a crush. Im so scared, but I think just the next step is getting to know him first thanks.

  6. Hi
    I am a 56 yr old male, had plenty of girlfriends, but really forgot how to go about asking someone out, now that i,m single again.
    I have found your page of advice very useful and making a lot of sense, will be trying it out soon !

    Cheers !