How to Ask a Guy Out: 3 Foolproof Ways to Get an Awesome Date

If you’re wondering how to ask a guy out, fear not! We’re here to talk you through different ways to make an amazing connection and get the date of your dreams. It’s not as hard as you might think!

Why you should learn how to ask a guy out

If you’re reading this article, you’ve probably started to think about how to ask a guy out, maybe you even have someone specific in mind, but you’re wondering if should you take the plunge? It’s always going to be scary to take a risk and put yourself out there, especially if you’re used to guys asking you out instead of the other way around! So, if you’re still on the fence about whether or not you should take the plunge, allow us to tell you why we think it’s a great idea.

A group of friends smile and laugh while hiking together


It’s a confidence boost

Learning how to ask a guy out will boost your confidence, plain and simple. Instead of waiting around for something to happen, you’re owning your power and going after what you want. Even if you step out and don’t end up getting the answer you wanted, you’re still going to be proud of yourself for trying! In fact, sometimes failure can be the best thing for us. Once you’ve experienced the worst-case scenario, you’ll realize that it’s not as scary as you might think. 

Guys appreciate it

Something that stops some people from learning how to ask a guy out is that they worry that guys are put off when someone is bold enough to approach them. Nothing could be further from the truth! In fact, there are whole businesses like the dating app Bumble that work on the premise that guys like to be asked out. In a culture that primarily puts the pressure on guys to initiate, it can be incredibly refreshing, and, yes, attractive, when someone else makes the first move.

How to ask a guy out when you don’t know him

This is for the random stranger who catches your eye. Whether that’s in a coffee shop, at an event, or even at the grocery store, this probably takes the most courage because you don’t know anything about this person! But there’s nothing stopping you from finding out more, right?

A couple sit on bleachers while smiling at each other and holding iced drinks

#1 - Make eye contact

Make a connection by catching the guy’s eye and smiling. If he doesn’t smile back, or if he seems to shut you down right away, this could be a signal that he’s not single or interested. 

#2 - Start a conversation

This could be as simple as saying hi. Make some normal small-talk or ask him a question just to start up a conversation. Don’t overthink this part, just remember you do this all the time.

#3 - Get to the point

There’s no need to stretch out the conversation unless it’s going really well. Chat until you reach a natural pause, and then just be honest. Say something like, ‘I’d love to hang out sometime. Do you think I could get your number?’

If he says yes, amazing! Get his number and text him to set up your date.

If he says no, just remember that it may not be a personal rejection no matter how much it might feel like it in the moment. He might be seeing someone else, or only visiting your area. You don’t know the backstory, so don’t let embarrassment fill in the blanks. Stay polite and say something like ‘That’s okay, I just thought I’d ask! It was nice to meet you.’

How to ask a guy out when you’re already friends

Even if learning how to ask a guy out when you don’t know him feels pretty risky, it can almost be more nerve-wracking when you do know him! No one wants to make a friendship awkward or feel the pain of rejection. But if you have feelings for one of your friends, waiting around and never saying anything can be worse! Here at the Adventure Challenge, we think some things are worth risking for, and this is one of them.

A couple smiles at each other while leaning over opposite sides of a bannister that's part of a carnival ride

Our advice for how to ask a guy out is this: plan the date before you ask him.

Sounds weird, right? But here’s the thing: a specific invite is always going to sound better than a vague ‘date’. ‘Let’s hang out sometime’ is not as inviting as ‘I have a spare ticket to this concert. Wanna come?’ 

So, come up with a fun activity you’d love to do together and invite him. Then drop the ‘d’ word: tell him you’d love for it to be a date! It’s so important for you to be clear about this, because you don’t want to show up for the date and realize that he thinks he’s just hanging with friends.

If you’re nervous, remember, this guy cares about you. He’s not going to embarrass you or think less of you for being bold!

At the end of the day, dates are fun. (Especially when The Adventure Challenge date ideas are involved!) Being asked out is fun - and learning how to ask a guy out can be fun too.

How to ask a guy out over text

A lot of the same guidelines for how to ask a guy out in person also apply to asking him out via text. But, because you don’t have the benefit of body language and tone of voice, it’s extra important to be very clear when you’re asking someone out over text. Using the word ‘date’ is almost definitely a good call, here.

Close up image of a female texting to ask a guy out on her iPhone

There are two different scenarios where you might find it easier ask a guy out over text:

#1 - You don’t know him, but he gave you his number or you got his number from a mutual friend

In this scenario, you want to start by introducing yourself and explaining the connection before inviting him to hang out. ‘Hi, I’m ____. It was great to meet you last night / _____ gave me your number. I’d love to get to know you more. Do you want to grab coffee this weekend?’ 

You could be general and simply say ‘Do you want to go on a date this weekend?’, but, like we’ve already discussed, it’s often best to offer a specific activity or plan.

#2 - You know him and you already text

You might already know the guy you want to ask out, but what if you don’t see him in person all that often? While asking someone out face-to-face is usually better than over text, sometimes digital communication is your best option.

There’s no rocket science to how to ask a guy out over text. Message him and ask if he wants to do something with you - make it specific. Dinner, coffee, a walk; you know what would suit you two the best. Keep it lighthearted and low-stakes, and, for extra clarity, add ‘I’d love it if this could be a date.’

Learning how to ask a guy out

There you have it, three different ways to get a date. You should be able to see that, while it’s nerve-wracking, learning how to ask a guy out is actually pretty easy! Be honest and straightforward and you won’t have a problem.

If you want some easy prompts for first date ideas, check out our incredible Blind Dates card pack. And once one date turns into two or three, check out the Adventure Challenge Couple’s Edition for 50 incredible, out-of-the-box date ideas! 

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