How To Ask A Guy Out (15 Ways To Initiate A Date With A Guy)

Last updated on June 12, 2022 by April Maccario

Do you ever wonder how incredibly cool the 21st century is that you can do many things without raising eyebrows? 

A woman can decide to be a single mother, date as many times as she wants, and as weird as it seems, she can stay single yet have a fun-filled life by marrying herself. So yes, it’s a crazy yet liberating world out here these days. 

Out of all the things women can do now, asking a guy out is one that has gained popularity. In fact, making the first move to ask a man out or propose is no longer a strange thing to do.

However, as common as women making the first move has become, it can still be a risky act because everyone fears rejection, especially women. 

Have you been holding on to a huge crush and want to know how to ask a guy out? Do you not want to wait around for him to realize what he is missing without embarrassing yourself? Here are a few ideas to make that happen.

15 Ways To Ask A Guy Out

1. Organize hangouts based on mutual interest

organize hangouts based on mutual interest

For us women, knowing how to ask a guy out on an official date means playing it safe from the start. If you go ahead to ask him out from the first day you met him, the idea might backfire. Ease him into the interest by organizing hangouts based on something the both of you like doing or a place you both visit a lot.

If you both love playing games you can invite him to an indoor gaming center. He will be comfortable with you and that way you will get to know him better and eventually ask him out.

2. Be confident even if you’re nervous

Confidence is sexy and empowering and that’s exactly what you need if you want to get that man to say yes to you. Men love it when women are confident

Does that mean guys want us to make the first move? Well here’s the truth, some men don’t mind at all! The idea might seem bold, but this person doesn’t bite does he?

Give yourself a pep-talk, practice the scenario with someone close if it will help you feel better but, don’t meet up with your crush until you’ve mastered how to ask out a guy.

3. Dress in comfortable but classy

Your outlook says a lot about the kind of person you are, and guys are drawn to women who look like they know what they want. You don’t need to overdress or dress to kill but, make sure you dress in an understated way that still shows you’re trying to make your crush notice you.

One other thing you can do is put on sexy lingerie, not because he can see it but, because of how it will make you feel. You will feel sexy, desirable and in your mind, you’re thinking ‘this man will be a fool not to like me back'. When your dressing matches your confidence level, the person in question will be more intrigued.

4. Take a trick from the guys' handbook by doing what they would do in your situation

Manuals are there to guide us and help us avoid trial and error. However, if you want to know how to ask a guy out, you may have to mirror the guys’ themselves. 

You’ve had guys ask you out in the past, how did they make the first move? What did they do while making the first move? Where did they take you? The whole idea of this is to mirror men and how they successfully get women to say yes. So, if you want to know how to ask a guy out, study the way men ask women out.

5. Use humor

When you want to ask someone out, you should have a few tricks up your sleeves. Your love interest might be the kind of person who needs humor to get your point. Almost everyone loves to be put at ease before making any sort of commitment and that’s exactly what humor achieves.

While in the middle of a discussion you can just throw in a light “don’t you think I’m the sweetest person to date?” From his answer, you’ll know if he sees you as someone he can date or not. If you have been spending some time with each other, that simple funny question will reveal how this person feels about you. 

6. Take the direct route

There are times when a direct approach works best. It’s even better if you have taken the time to understand what appeals to your crush. If he’s someone that likes straightforward conversations, then go straight to the point.

He could be the shy type who isn’t sure you like him either or he could be someone who doesn’t like the idea of small talk. Even if you aren’t so sure of his personality or how he would take your request, just ask him to so you can know for sure. If he says yes, that’s great, and even if he turns you down, you still get extra points for trying.

7. Ask him out during a phone conversation

ask him out during a phone conversation

Many people start their relationships online before finally meeting face to face. So, it is perfectly alright if you ask a guy out during one of the many phone conversations. 

Obviously, the guy would be someone you’ve spoken to a couple of times and you just want to know him in person. This is by far the easiest way to ask someone out because you won’t see him reject you and he won’t see your crushed look. Also, you and your crush will get to talk a lot without any expectations before the main date.

8. Take him out on a special date

Is it your birthday? Did you get a promotion at work? or you just had a successful surgery and want to celebrate? 

Celebrations are great opportunities to ask someone you like out. Most people like to enjoy on their own regular days, your crush will most likely enjoy doing the same.

Your joyous occasion is a good time to invite your crush on a date. Of course, he doesn’t need to know beforehand that it is a date. You can inform him you just want to grab a drink or a quick dinner to celebrate and you want him to tag along. You can pop the question in between the celebration.

9. Acting coy works too

Acting coy is a woman-power that you shouldn’t be ashamed or scared of wielding. Here is someone you like and hope will mean more to you, so send him that half-completed text message, ask an open-ended question, let him guess that you want more but don’t say it directly.

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The coy act drives men crazy but you can do yours in a cool way that leaves enough hints for him to catch up with your interest in him. If you do your part well, he will say yes when you finally ask him out.

10. Create scenarios that require that he helps you out

Keeping close contact with the guy you like is one way to make sure he starts growing interest in you too. Most men love acting the hero and so, they will answer when you tell them you need their help.

Call on your crush for help, even if you can handle the situation. Do not do this often to avoid him thinking “what the heck!” but, do it occasionally until he becomes a regular part of your life. Helping you means he’ll know so much about you, so make sure you tell him things about you. If he likes you in return he will accept to go out with you. 

11. Do the unusual

Don’t go crazy on him or anything like that but, try doing silly stuff that will make him laugh and take more interest in you than usual. Send him handwritten sweet and cheesy notes that will leave him wondering if you’re from this century. 

When you’re together on a cold night, ask him to give you his sweatshirt to keep you warm. Then refuse to return it immediately because you want to take it to the dry cleaner first. Don’t hold on to his items like you want to own them or he might draw a line restricting you from his life. Just make yourself a part of his life as much as possible.

12. Invite him to a group hangout

One way to be inconspicuous about asking a guy out is to invite him to a group hangout. If he refuses to attend, he isn’t rejecting you personally. If he says yes, you have the chance to work on him without him knowing. During the hangout, ensure you stick close to him while you still interact with everyone else. 

Use that period to know some things about him and tell him about yourself too. If all goes well, he will want to hang out again, this time with only you. 

13. Get to know him by asking questions

There is hardly anyone who doesn’t like it when people show genuine interest in them. If you want your crush to notice your interest in him, you need to ask him questions that show you’re interested in his life. 

You can offer information about yourself, then ask him if he has experienced something similar. People like to swap similar stories and empathize, so he’ll feel connected to you. It shouldn’t be too hard to get him to go on a date with you when he finally opens up.

14. Show your interest through nonverbal exchanges

show your interest through nonverbal exchange

Body language is a big part of the process of asking someone out. If you’re saying one thing but your body is saying something else, you may confuse the guy. Let your body and words do the talking at the same time. 

While you’re letting him know you like him, your hands shouldn’t be together like a scared girl. Instead, you could sweep your hair behind your ears or do something sexy like licking your lips slowly to show a hint of vulnerability. 

15. Ensure he’s not in a relationship

Before taking that bold step, are you sure this guy isn’t in a relationship? Yes, I might seem dumb for asking but it’s important. See, going after a guy in a relationship is a recipe for failure, cause he’s already seeing someone else. Making advances at him could either be successful or not, but are you ready to risk that?

Plus, if you get rejected, you’ll probably make a new enemy- his current girlfriend. So, do your homework and ensure he’s up for grabs before investing your emotions on a moving train.


What is a cute way to ask a guy out?

One cute way to ask a guy out is by leaving him a note on his desk, slipping it to him while you’re both on the bus, or even writing the words on his palms. You’re not saying it out loud but your cute way of saying it will make you all the more attractive to him.

How do I ask a guy out over text?

If he is a guy you’ve been in contact with over time you can just tell him that you’d like to go out with him. If you’re a bit unsure, you can text him to meet you for a drink and take it up from there.

How do you ask a guy out without asking him out?

You can ask him to hang out with your mutual friends or tell him you need a plus one for an emergency event. If he is a nice guy he will go with you without much hesitation. 

Is it OK to ask a guy out?

There is no shame in asking a guy out, especially in this advanced age where so many new inventions keep popping up. Also, some guys aren’t aware that certain girls like them until it’s too late. By asking a guy out, you shorten the round-about process of discovery. 

How do I ask out my crush?

You can ask out your crush directly, take your time or give him hints that will make him ask you out by himself. A combination of the right words, good body language, and direct interest will help you with asking your crush out.

In Conclusion 

There is absolutely no shame in asking a guy you like out but, the fear of getting a ‘no’ can make you hold back. If you decide you really want that guy in your life, use the tips in this article to get him to say yes to your official first date. 

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Do you hate it how everything seems to always revolve round him while you just seem to be an afterthought sometimes?
We hear this all the time from women that contact us asking for help with their relationship.

It almost makes you wonder whether he actually likes you or whether he's just stringing you along.

Why don't you take this quick free quiz to see if he actually likes you!

April Maccario
I'm a huge nerd when it comes to understanding how relationships between men and women work, and what drives a certain behavior. I spend much of my time getting into the nitty-gritty and try to share my findings on this site with the hope of making life a little easier for women that are struggling in their relationships or love life.

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