How To Win At Asking Someone Out

Asking someone out can be a daunting task. I’m here to help.

Because we all know there is nobody more equipped to give advice on how to deal with the opposite sex*. I mean, look at me. I’m a beacon of grace and beauty.


How to Win The Break-up, How to Win At Dating and How to Win at Sex are some of my personal all-time favorite things** I’ve ever written.

But how to get to ALL of that stands and falls with how good you are at asking someone out.

We shouldn’t always be sitting around waiting and wishing for the boy or girl to ask US, sometimes we gotta grab life (not them, be nice) by the balls and ask for what we want.

Here’s how to do that in a relatively safe and easy way!

*Or the same sex. Date who and whatever you want. (This article I’m using the He-She one because it’s still most common. For now…) 

**Other items on this list include my e-book Habits, about 200 words of my upcoming book (lol) and a grocery list that only featured the different Tony’s Chocolonely flavours. 

Pro tip: Follow the advice, not the pictures.

READ THE SIGNS There’s three possible reasons why you can’t tell if a guy likes you.

One, you’ve been raised by wolves and are incapable of reading other people because of your stunted emotional development.

Two, the guy in question is TERRIBLE at flirting.

Three, he does not like you.

One can be fixed. Really look. Pay more attention. Be on the look-out for approach-behavior.

Approach behaviour is what I call what people do when they are drawn to you. Coming over to say hi, waving from across the room, making eye contact, staying near you for some reason, interjecting themselves in conversations you are having.

Additionally, watch out for smiles, jokes, them saying your name, giving you nicknames, them touching your arm and other relatively unnecessary physical contact.

If you think the guy might just be horrible at flirting, initiate some more. Make a joke here and there, drop a compliment, smile, do that dumb-as-shit hair twirl thing in front of them. See if you get any positive response, no matter how awkward.

If there’s no signals indicating interest in you, and you don’t even get a lukewarm reaction when YOU flirt? And it has been this way for a while, with no change?

He does not like you.

So don’t ask him out. Desperation isn’t sexy and if he says ‘yes’, it’s probably just because he knows he can, you know? Not good for either of you.

LAY OUT SOME GROUNDWORK I have some experience with just flat-out asking someone out and I do not recommend it.

Why not? Because guys are pussies who scare easily and a woman who knows what she wants can be about the scariest thing there is.


It’s more that it can come off too strong, and coming on too strong can be a turn off to either of the sexes.

There’s three easy ways to lay down groundwork for asking someone out.

Number one? Do the “oh, we should totally do that sometime!” move when you’re talking about a mutual hobby or activity.

Their response to this can be SO incredibly telling on whether or not they would like to spend more time with you:

  • If they respond enthusiastically and get out their planner straight away, you’re basically DONE BAM CONGRATS ON YOUR DATE AND YOUR FACE.
  • If they respond enthusiastically and later on THEY bring it up again, all you have to do is ask when they are available.
  • If they respond enthusiastically and don’t mention it again, but respond with the same enthusiasm when YOU bring it up again? Make a date.
  • If they respond enthusiastically and when you bring it up again the enthusiasm has waned or they remain vague on the specifics, they might just have responded enthusiastically out of a courtesy and this might not be a thing.
  • If they are uninterested from the get-go, you know where you stand. You’re now starring in Their Loss, The Musical.

Number two, ask them along to something you’re going to do anyway.

If you’re going to study in the library anyway, ask them if they want to tag along. If you are going to try out a new recipe and you know they like cooking, ask them if they want to join. If you’re planning to go wherever, ask if they have plans right now and if they’d like to come with you.

If they have the time and interest, they will come along. If they have the interest, but not the time, their response will tell you so.

And number three, you can invite them along to group things with your friends if they aren’t total assholes about new people or you liking someone. This works especially well if they already know one or two of your friends, but if your friends are nice and non-threatening and the person you want to date is not a scaredy-pants this will work out fine too. Just spending some more time with the person you want to date eventually is good.

ASK. AND ASK RIGHT. Remember, when you’re asking someone out it’s always possible they will say ‘no’, but it’s less likely because of you paying attention to the signals and paving the road to DATE VILLE.

I think the best way to ask someone out is roughly as follows: At the beginning of a week, whether in real life or via text, be like “hey, do you maybe want to [SPECIFIC ACTIVITY] with me this weekend?”

It’s specific enough, it’s in the near future but still leaves room for Friday, Saturday or Sunday and it comes across as just a genuine, relaxed question.

Now, someone has three options to choose from and to offer you, and if their weekend is already full, they can provide an alternative date – either during the week or the next weekend- that works for you both.

ASK ONCE AND ONLY ONCE. If they say ‘no’ without offering a satisfying alternative or explanation, or they say ‘yes’ but never set a date? Okay. Clearly, it’s not a priority for them. They’re not into you.

That sucks, but putting all the work into dating someone who isn’t into you is worse. So don’t ask again. If they change their mind, they can ask you.

Okay, once they’ve said ‘yes’ you’re on your own, darling.

Be your delightful self and a decent human being and all should work out just fine.

Happy dating!

PS: This weekend is Valentine’s Day. Don’t ask anyone you don’t know that well out for a date on Valentine’s Day. The implications of having a date on that pink and heart-filled day is enough to make any two decent human beings go a little crazy.

Wait a weekend for me, okay? Kthanksbye.

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  1. I laughed so hard Lianne! You’re writing is just so funny and your pictures are amazing 🙂 And I totally love your advice, although I have the sweetest boyfriend at the moment. Happy valentinesday!

  2. Leuk artikel! Ik deel je mening tov die paar how-to-win-at…-artikelen, ik vind ze heel leuk, al zijn ze geen van allen voor mij echt van toepassing op het moment dat je ze schrijft. Des te veelzeggender dat ik ze desalniettemin waardeer.

    1. Haha, gelukkig! En ik zal er ook nog eentje schrijven over How to Win At Happily Ever After! Hopen dat die wel van toepassing is! 😉