20 Cute Ways To Ask A Guy To Be Your Boyfriend

Last Updated on April 7, 2022 by Alexander Burgemeester

Are you thinking about cute ways to ask a guy to be your boyfriend?

There are so many different ways you could ask him, including sending him a handwritten letter, asking him out on your birthday, or getting your friend to do it.

Asking a guy out isn’t the norm because, in general, men are the hunters. When they see a woman they like, they enjoy pursuing her until she’s his girlfriend.

They take great pride in the chase, but some men don’t have the confidence to go after the women they want.

If you’ve been dating a guy for some time, or you have a male friend you’re interested in who has yet to make a move, it could be that he likes you, but he’s not confident enough to ask you to be his girlfriend.

Life is too short to miss opportunities; you never know what could happen if you ask him to be your boyfriend, he might be the ‘one.’ If you are ready to ask the guy you’ve been crushing on out, here are twenty cute ways to ask a guy to be your boyfriend. 

How To Ask Someone To Be In A Relationship

How To Ask Someone To Be In A Relationship

So, you’ve been dating for a while, you think he’s boyfriend material, but he hasn’t popped the question yet.

You’re tired of waiting, and you’ve decided to ask him yourself. Here are five ways to do it:

  1. Make sure he likes you first.
  2. Don’t ask during sex.
  3. Don’t confess your undying love.
  4. Don’t ask when you’ve been drinking.
  5. Be casual about it. 

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#1 Make Sure He Likes You First

If you’re dating the guy, this doesn’t apply to you because he clearly likes you; he just hasn’t asked you to be his girlfriend yet.

But if he’s a male friend, you want to make sure he likes you before you go and make a fool of yourself.

Asking is out of the question, but his body language will tell you everything you need to know. Look out for the following: Do his pupils dilate, or does he lick his lips a lot when he’s talking to you?

That means he thinks you’re hot. Does he stand with his legs shoulder-width apart and his hands on his hips when you’re around? 

Body language experts call this the superman pose, and it means he wants you near his groin area! You can also flirt with him a bit to see if he flirts back. Once you are confident he likes you, then ask. 

#2 Don’t Ask During Sex

Men are not thinking straight when they’re having sex. They are in the moment, having a great time and the last thing they want to do is have a conversation.

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Also, he might be so turned on that he says yes to your request even if he doesn’t mean it.

Then afterward, he thinks about it and regrets it. If you’re going to have a conversation with the man you like about taking things to the next level, make sure you do it with your clothes on! 

#3 Don’t Confess Your Undying Love

Please don’t embarrass yourself and tell your guy friend you’re in love with him; he’ll run a mile!

The fact that you’ve got to do the asking means one of three things. He’s either really shy; he’s still trying to figure out whether you like him too. Or he’s not into you.

In case he’s not into you like that, you don’t want to make a fool of yourself, so don’t get all intense about things. 

#4 Don’t Ask When You’ve Been Drinking

It might sound like a good idea to ask out your love interest when you’re tipsy, but it’s not. Alcohol makes people do and say things they wouldn’t normally do.

When asking a guy to be your boyfriend, you want the both of you to be in your right mind. He might say yes, and then regret it in the morning.

Or he could say no and regret it in the morning. Either way, he’s said something he didn’t mean, and it will either lead to a very short-lived romance or no romance at all.

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#5 Be Casual About It

Men don’t like feeling pressured to be in a relationship; they prefer things to happen organically.

If he’s feeling you, he’ll wait for the right moment and let you know. In most cases, he’s not going to drop on one knee and ask you to be his girlfriend; he’ll try and play it cool because he doesn’t want to appear needy even if he likes you a lot.

So take the same approach as him and be casual about it. Don’t do the whole “I need to speak to you about something important” speel; it will worry him.

Then when you do have the conversation, I can guarantee you he’ll say something like, “Oh, is that it? I thought it was something important.”

Not because he’s not taking you seriously, but because the beginning of a relationship is never a big deal to a guy. 

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20 Cute Ways To Ask Someone To Be Your Boyfriend IRL

Asking someone to be your boyfriend is intimidating and nerve-wracking. If you’re just friends, you’re not sure whether the feeling is mutual; and if you’re dating, you’re not sure if he wants to take things further.

Some cute ways to ask someone to be your boyfriend include: Send him a handwritten letter, ask him out on your birthday, and ask him out during a game of truth or dare.

Here are twenty ways to ask someone to be your boyfriend. 

20 Cute Ways To Ask Someone To Be Your Boyfriend IRL

#1 Send Him A Handwritten Letter

A handwritten letter is a meaningful way to show someone you care. In general, people don’t write handwritten letters anymore.

These days, everything is done on a computer, whether it’s through email or typed out on a word document. A handwritten letter shows you’ve put effort into telling him how you feel. 

#2 Ask Him Out On Your Birthday

Depending on how close you are, he’s either going to take you out for your birthday or call and wish you a happy birthday.

Either way, during your conversation, you can say something like, “Do you know what the best birthday present would be?”

When he asks what, say, “to have a boyfriend just like you.” He’s either going to respond with, “I can be your boyfriend,” or if he’s not looking to take your friendship to the next level, he’ll come up with an excuse and say something like, “Oh no, you wouldn’t, I make a terrible boyfriend.” 

#3 Ask Him Out During A Game Of Truth Or Dare

Make sure you’re alone for this one so he can’t get away with saying something like, “Can we talk about this later, please?”

The truth question will be, “will you be my boyfriend?” If he chooses dare, it means he doesn’t want to answer the question, and he probably doesn’t want to be your boyfriend. But if he says yes, you’re good to go! 

#4 Get a Friend To Do It

If you really can’t stomach doing it yourself, ask a mutual friend to help you out.

Get her to call or meet up with him and explain that you really like him and would like to ask him out, but you’re too shy. 

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#5 Just Do It

Don’t waste time with any extras; just tell him straight. You can either arrange to meet with him or wait until your next date.

Wait for the right moment, and just tell him how it is. He’s either going to say yes or no. 

#6 Write Him A Poem

Writing a poem is a really cute way to tell your guy friend you want him to be your boyfriend if you’ve got some poetry skills.

You can write about why you like him, from his looks to his personality. He’ll be so chuffed by the end of it; he won’t have any choice but to say yes!

#7 Send Him A Text Message  

Text messages are a great way to ask someone out because it removes the awkwardness out of the situation. It also gives you a get-out clause if he says no.

You can basically say, “Oh, I thought I was talking to someone else.”

Start a conversation, and then casually drop the question in and see what he says. 

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#8 Play A Song Over The Phone

Find a song about women asking men out on dates or a girl asking a guy to be her boyfriend.

Call him and tell him to listen to the song; he’ll most likely ask you why you asked him to listen to it when it’s over.

You can then say something like, “because I was too shy to ask you myself, so I thought I’d get (name of the person who sings the song) to ask you instead. 

#9 Ask Him To Help You With Something

Men love helping women; it makes them feel manly. Ask him to help you do something strenuous around the house, like mowing the lawn.

He’ll be all hot and sweaty; you can make him a cold drink and tell him how much you appreciate him helping you out, especially because you love seeing him dripping with sweat. Pay attention to the energy; if it’s right, ask him to be your boyfriend. 

#10 Get Him To Ask You Out

This one will only work if he gets the hint. During a conversation, keep dropping hints that you would like him to ask you out.

Say things like, “It would be really cool if someone would ask me out.” Or, “I would love to be a certain person’s girlfriend.” But be over the top flirtatious with it, so he knows you are talking about him. 

#11 Set Up A Treasure Hunt Game

During Easter or Halloween, set up a treasure hunt game. Wrap up the gifts, and one of them will be a note asking him to be your boyfriend. 

#12 Offer Him a Piece of Gum

Buy some gum with wrappers, open them carefully and remove the stick of gum. Write the question, “will you be my boyfriend?” inside each wrapper, and offer him a piece of gum. When he opens it, he’ll see the question. 

#13 Present Him With A Journal

You might have to wait a while to do this one, but it’s sweet, so it will be worth the wait. Every time you go on a date together, take pictures, print them out and stick them in a journal.

Write about the date, how awesome it was, and how he made you feel. After the tenth date, write the question, “will you be my boyfriend?” on the page.

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#14 Put The Pressure On

Only do this if you’re sure he likes you, or you’ll embarrass yourself in front of a lot of people. Wait until there’s an event like a friend’s birthday or something.

Get the D.J. to give you the mic in the middle of the party and ask him to be your boyfriend. 

#15 Change Your Name In His Phone

Ask to borrow his phone to send a text to your mom because your battery has died. Actually send a text to your mom, by the way.

And at the same time, change your name on his phone to, ‘my girlfriend.’ Go to the bathroom and call him; when he answers the phone and asks, “Who’s this?” respond, “It’s me, (whatever your name is).

When he asks why does your name come up as, ‘my girlfriend’ reply, “I don’t know, do you want me to be?” By now, he would have guessed that you changed your name when you were sending the text. 

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#16 Make Him A Video

If you’re too nervous to ask him out face to face, make a cute video of you asking him.

There are plenty of apps you can use to make the video look super cute. Send it to him and see how he responds. 

#17 Let It Slip

During the conversation, call him your boyfriend and see how he reacts. You can say something like, “I was speaking to my friend the other day, and she asked who I went to the cinema with, and I told her I went with my boyfriend.”

Obviously, he’s the guy you went to the cinema with so he’ll know you were talking about him. 

#18 Compliment Him First

Everyone loves praise, and complimenting your guy friend before asking him to be your boyfriend will make him feel good about himself.

Don’t compliment his looks because he’s probably heard it a thousand times before; instead, say something about his personality.

Since men are naturally protective over the women they’re attracted to, if you say something like, “I feel safe around you,” it will boost his ego and hopefully make him want to be your boyfriend so he can protect you even more. 

#19 Invite Him To A Wedding

Inviting someone to a wedding is a big deal because it’s typically a couples event.

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When you ask someone to accompany you to a wedding, you’re basically saying, “I can see myself being in a relationship with you.”

If he agrees, you’re halfway there, and if the vibes are right at the wedding, ask him to be your boyfriend. 

#20 Buy Him A Gift

Don’t buy him a gift out of the blue, wait for an event like his birthday, or he has something to celebrate like passing his exams.

Make sure you wrap the gift up in a box and place a note on top saying, “Will you be my boyfriend?” When he opens the present, the first thing he’ll see is the note. Please pay close attention to his facial expression when he reads it because it will tell you everything you need to know.

At that moment, he’ll either say, ‘yes,’ ‘no,’ or ‘I’ll think about it.’ If he says ‘no,’ you can worm your way out of the embarrassment by saying, “Oh my goodness, that note wasn’t meant for you. I put it in the wrong box; how embarrassing.” Then continue on as normal. 

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How To Ask Someone To Be Your Boyfriend Over Text

Asking someone to be your boyfriend over text is risky because you can’t see his reaction.

But it can still be done; here are three ways to ask your guy friend to be your boyfriend over text: Use humor, use proper language, and wait for a congratulatory moment. 

How To Ask Someone To Be Your Boyfriend Over Text

#1 Test The Waters

When speaking to the guy you like over text, ask him questions about relationships. Don’t make it seem like you’re interrogating him.

Instead, every so often, drop a comment about how you feel about relationships and see how he responds.

If he responds in a positive way to one of the comments, take it a step further. For example, ask him a question like, “If you were going to take a girlfriend to see a film, which film would he take her to see and why.”

A question like this will open the door to a discussion about how he likes to treat his girlfriends. When you feel the time is right, ask him out. 

#2 Use Humor

Only use humor if you know he finds you funny, or it could backfire on you. Humor is always good when it comes to serious topics.

Let’s face it, your reputation is on the line if he says no. You need to be able to look him in the eye again if he rejects you.

Making a joke out of it is a good way to keep things light, and if you don’t get the response you were hoping for, you can brush it off as a joke.

You could say something like, “Are you hungry? I’ve just ordered take-out for my boyfriend and me.

Would you like to come over and help me eat it?” Or, “I’ve been meaning to ask you to be my boyfriend for a while, but I’ve been super busy reorganizing my kitchen cabinets.”  

#3 Use Proper Language

People no longer have normal conversations in the digital era we’re currently living in. Text messages are spoken in code, and if you’re not down with the lingo, you won’t understand what the person on the other end of the line is on about.

Even if you do talk that way with your guy friend, you want to make sure what you say isn’t taken out of context. Therefore, use proper language to ensure you’re both on the same page. 

#4 Wait For A Congratulatory Moment

Congratulatory moments are a great way to ask someone out over text because it’s normal to praise someone when they’ve achieved something noteworthy.

The intimidation factor has been eliminated, and you can keep it casual by saying something like. “I’m super proud of you. Would you like to add one more achievement to your belt and be my boyfriend?” 

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Final Thoughts

Now that you’ve got twenty cute ways to ask a guy to be your boyfriend, it’s time to execute some of these ideas.

Make sure you look super hot when you do it so that he’s so enamored with your beauty, he has no choice but to say yes.

Also, remember to play it cool; the desperate look isn’t cute. You need him to think he’s the luckiest guy in the world to have someone like you on his arm.

Don’t get arrogant with it, but exude a certain confidence that lets him know you could have any guy you want. But on this occasion, you choose him! You will also need to brace yourself for rejection because he could say no.

In some cases, it might not even be that he doesn’t like you, but that he’s not ready for a relationship.

If that’s the case, don’t take it personally; brush it off and keep it moving. Finally, I wish you all the best in asking a guy to be your boyfriend.

Photo of author

Alexander Burgemeester

Alexander Burgemeester has a Master in Neuropsychology. He studied at the University of Amsterdam and has a bachelor's in Clinical Psychology. Want to know more?

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