How to ask a guy out over text in a cute way (A step-by-step guide)

“Will you go on a date with me?”

Imagine reading these exact words from your Whatsapp or phone inbox. Don’t even think of a face or name. Just focus on the words.

Stare a little bit longer and it will start to feel as intense as “Will you marry me?”

It’s just too darn serious!

No matter who sent it to you — whether it’s a guy you’re obsessed with or some stalker you wish would disappear off the face of the earth — I’m sure your heart would freeze for a millisecond the moment you read those words.

This kind of text is so direct that not only is it uncreative, it can make the receiver feel a little pressured.

I mean…if you’d say YES, they might assume you like them a ton and would want to be their girlfriend the next day and if you’d say NO, they might feel that they’re ugly and insufferable.

The way we word our invitation when asking someone out definitely matters a lot so don’t come on too strong when texting a guy you like!

You want to make your texts cool and casual, not stiff or creepy, or desperate. It should seem like you didn’t give it much thought.

I know you agree with me 100% on this because this is quite obvious, right?

The thing is…it’s just not so easy to pull off.

It takes some charm, some skills, and a lot of practice. However, you don’t have to be a wordsmith or a highly sensitive person to get it right. Anyone can be good at this.

In this article, I will share with you some sneaky tricks (and examples) on how to ask a guy out over text in a cute way.

Three texting and seduction basics:

1) Words are not just words

Learning a thing or two about interpersonal communication is a must because the words we use, our body language, and the medium of communication we choose all contribute to the effectiveness of messages we exchange with people.

One word can totally change the meaning and intention of a message so you gotta pay attention to the words that come out of your mouth and in this case, to the texts you send.

Especially because with text, once you send it, it’s in their inbox forever.

And not just the words!

Pay attention to the emojis, the exclamation points, the ellipses. Every text code you send matters.

Why is this important?

Before you can even ask a guy out, you have to flirt a little in person and over text, amirite?

You don’t want to just ask someone out if you only exchanged a few hellos!

Flirting is a smooth back and forth kind of seduction and it’s crucial that you know how to send flirty text messages and that you know how to decode them.

Even if you have the courage to ask a guy out if you don’t know shiz about communication and flirting, you won’t move forward and you’ll be stuck in the friend zone forever.


2) You gotta feel like a KWEEN!

You can’t ask a guy out if you feel like an ugly duckling deep inside. Trust me, it will show!

If you want to ask someone out, you have to think like you’re prettier than the Kardashians (because you probably are). You gotta believe you’re hotter than the sun!

You’re a kween and he should feel lucky you asked him out.

What’s the worst thing that could happen? He’d say no?

So effin’ what?!

Will you lose your savings? Your friends? Your family? No.

Will you lose a limb? Hell no!

Your life will go on and you’ll be in one piece like a badass kween who knows how to take charge of her life.


  • Get confident or fake it til you make it
  • Go to IG and search for confident girls and feel like you’re one of them
  • Watch Rupaul’s Drag Race and get the kween vibes
  • Read tips on how to love yourself more
  • Have other crushes so you won’t feel too invested in this guy
  • Learn not to take things too personally

3) Keep it light and casual

Good flirting means a lot of teasing.

Everything should be vague as if the other person is just imagining things.

It should be like touching someone oh so very lightly that they’re not sure if your finger actually touched them or it was all in their head.

Don’t ever make moves and drop hints that are too obvious. Keep it slow and interesting for as long as you can. Get things oiled up, so to speak.

This kind of subtle flirting can be difficult for many of us mere mortals but the good thing is that flirting can be learned.

Here’s an example:

“You’re very handsome” is too obvious.

“Wow! I like your eyes” is still somewhat obvious.

If you want to be cute and casual (and memorable!), say something like:

“Hey, I didn’t know you got blue eyes!” 

It’s subtle enough that he’d be confused if you’re flirting with him or not. This might make him pay more attention to you in return.


  • A little goes a long way when it comes to flirting (this includes texts)
  • Try to use a friendly tone
  • Yes, be obvious but say it’s a joke
  • Learn how to seduce a man with words

A step-by-step guide to asking a guy out

Step 1: Warm things up

Get a little bit closer, be a little friendlier.

As mentioned above, you gotta flirt a little before you ask him out.

All you have to do is up the intensity and frequency by a few notches. Send memes, ask him stuff…just be near the guy without suffocating him.

This will also give you a clearer idea if he likes you back and what type of attraction you actually have.

Step 2: Take note of his likes and dislikes

Is he into football?

Is his favorite color blue or orange?

What is his favorite food?

Alright, alright. You can easily get a lot of clues and information if you just check his FB or Insta.

What’s cooler though is paying attention to the things he says when you’re together and looking for the things you have in common.

Pay attention to the more unique and personal things he shares.

You don’t have to do many tricks when it comes to seduction! Don Juan is a good lover because he pays close attention to women.

The secret to being a good flirt is paying attention.

Step 3: Send a casual invite

You want a date that doesn’t seem like a date so that if you get rejected, it won’t be a very hard blow on your ego. Besides, you’re also just testing the waters so a cool approach is the only way to go.

And since it’s just a friendly kind of invite, you can ask again and again because they really didn’t turn you down, did they?

They’re free to say no because it’s not a serious invite anyway.

There’s always a next time for casual invites instead of the formal “Can I take you out on a date?” approach.

What’s cool with the casual approach is that it gives the impression that you’re NOT head over heels in love with him. That you simply just want to hang out.

Cool and classy is the way to go. I can’t stress this enough!

Here are some ways you can do it:

Play the damsel in distress

Guys want to help so if they kinda like you or consider you as a friend, it will be too easy for you to do this.

What are the things he’s good at? What are the things you need help with?

You gotta consider both.

Don’t be like Cady in Mean Girls who has to dumb herself down just to ask her crush for Math tutorial. You’d be wasting your time.

But look, it doesn’t have to be too hard to find something to ask for help for. Here are some examples:

“Hey, I need a little help with my car. Is it okay if you drop by to check it? I’ll cook pasta!”

“Hey, I need help replacing the strings of my guitar. Are you free tonight? Drinks on me.”

“There’s a spider in my bathroom and I’m all alone in the house. Help!”

These aren’t really the legit candlelight dinner dates with wine and roses but you know what?

You can have burgers after and lots of talks and isn’t that a date? I prefer that over the serious ones, tbh.

Invite him to do something you both like

You both like to play chess? What a great way to get intimate with his body and mind.

Is it a date if you really just want to play? Maybe.

Make sure you stare at him intensely and do other seductive moves that men can’t resist. Since you’ve already noted down the things he likes, this should be easy for you.

“Guess what! Our favorite band is coming to town. You going? Let’s!!!”

“Hey, the TV show we talked about will premiere tonight. If you wanna Netflix and chill, I’m all alone tanayt!”

“Wanna check out the latest Scorsese movie?”

Offer him something that’s free

So let’s say you got two free movie tickets that you have to use today and he talked about this movie a lot. Text him!

But if you don’t have a freebie, you know what? Buy a ticket and just lie. Just go ahead. No one will know!

Sneaky, yes. But you’re doing it for love so it’s still cute.

You can just confess to him later once you’re in a relationship. I’m sure he’d find it adorable.

“Hey, I got free coffee. If you’re around, you might want to get it. I’ve had two already.”

“I have 2 boxes of free pizza here. I need help!”

“I won two tickets to an all-expense paid trip to Costa Rica. You wanna join me?”

The last one’s quite extra but you get my drift.

Challenge him at something

So he said he’s good at bowling. But you’re the bowling champ in third grade!

Challenge him to a match and it won’t feel awkward at all.

Guys love a good challenge and he won’t even think you’re asking him out on a date because he’d be too focused on winning.

He said he makes the best lasagna? Challenge him to a cook-off!

Just a warning: Most men have fragile egos!

When you challenge him at something, make sure it’s not something close to his heart or connected to how he views himself. If he’s a noob guitar player, don’t show off how good you are.

Think of something safe and playful, something that won’t make him feel too bad if he’ll lose.

“I’m kinda bored, you wanna _____”

The importance of saying you’re bored is that it doesn’t make you seem like you’re crazy for him. Hey, you’re just bored AF and you just want company. That’s all!

Take a look at these:

“I’m bored, wanna Netflix and chill?”

“I’m bored, wanna explore the city?”

“I’m bored, wanna grab some drinks?”

See? Anything becomes casual if you put “I’m bored” at the beginning.

Don’t use it often though or he’d start to think you have no life. It’s a turn-off.

When it comes to long-term relationships, men don’t want to be with boring girls even if you’re hella pretty!

Show off something

This is kinda the same as the challenge trick above but here, the limelight is on you and only you.

I don’t mean that you should be full of yourself and go all ME ME ME. Who wants to spend a minute with someone like that?

By “show off”, I just mean share something in a nerdy way.

Here are some examples:

“ Hey, I remember you wanted to see my vinyl collection. My records arrived today. Wanna check them out? You can borrow one if you like.”

“Hey, wanna see the treehouse I built? I just finished it!”

“Hey, I just cooked the best paella in the world. Drop by if you want some!”

Ask for his advice

Maybe it’s true that guys want respect more than love. They want to feel that they’re smart and that what they think matters. If you ask for his advice and opinion, he’d find it hard to resist.

“I just finished my short movie. Can you drop by to give me feedback? I’d totally appreciate it.”

“Hey, what do you think of this song I recorded?”

Of course you will go to a restaurant to discuss because you owe him at least a good meal for giving you his precious advice.

Step 4: Prep for a date or invite him next time




There are only three possible answers when you ask someone out.

Now, you have to know that even if you applied all tips and tricks above, even if he’s really into you, there is still that possibility that he’d say no.

There could be a million reasons why someone would say no to an invitation. It could be that they’re busy, they’re shy, they’re depressed.

If your guy says no to your invitation, it doesn’t automatically mean they don’t like you!

If he says no, try again next time. And next. And next.

If he keeps rejecting you, you know what to do.

If he says yes, then start getting ready for a date! Choose a good outfit and a good perfume. Prepare to have a good time!

Step 5: Feel awesome either way

Whether he’d say yes or no, you have to congratulate yourself for going after what you want.

You went after a guy like a badass woman even if everyone says we should just wait for guys to do the first move.

Isn’t that something to be proud of?

You’re still learning the whole dating and seduction thing and it’s great that you have someone to practice these skills on. You might end up together with this guy or not. That shouldn’t be the end goal (although that’s cool too).

What’s important is the courage, self-confidence, and the skills you’ve developed as you keep pursuing the things that matter to you.

Go ahead, ask that guy out. There really is nothing to lose.

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Lachlan Brown

I’m Lachlan Brown, the founder, and editor of Hack Spirit. I love writing practical articles that help others live a mindful and better life. I have a graduate degree in Psychology and I’ve spent the last 15 years reading and studying all I can about human psychology and practical ways to hack our mindsets. Check out my latest book on the Hidden Secrets of Buddhism and How it Saved My Life. If you want to get in touch with me, hit me up on Facebook or Twitter.

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