How to Ask a Guy Out the Right Way

Asking a guy out can be a daunting prospect. Just because men are historically the ones who do the asking, doesn’t make it any easier either. Although we tend to naturally feel out social situations and have good instincts for chemistry, our brains can’t help but default to the worst-case scenario.

But when it comes to tips for asking a guy out, you can never go wrong with using initiative – those butterflies in your stomach just show that it means something to you. So let’s look at how to ask a guy out while conquering your fears and boosting self-confidence.  

Some of the benefits of being the one to ask the guy

It’s completely understandable to feel anxious and intimidated by the notion of approaching a man and asking him out. A University College London study found both socially anxious and confident men showed significantly increased stress levels initially, even when approached by a digital woman in virtual reality¹.

This is called approach anxiety. When considering how to ask a guy out, gender roles are very much baked into our behavioral scripts. But this is also why subverting them can be so effective and refreshing.

Benefits of taking the initiative:

• It immediately puts you on a powerful footing. You’re in control of the interaction and while that puts guys on the back foot, they’ll be more vulnerable and prone to self-disclosure, and you can establish compatibility. 
• Some people think it comes across as intimidating but it’s quite the opposite. It just shows confidence, self-reliance, friendliness and assertiveness. And putting aside creative ways to ask a guy out, being flirted with is just plain flattering. 
• Lastly, it puts you behind the wheel of your dating journey. Why should male initiative dictate your dating life? Approaching gives you the agency to write your own story, on your terms.

Now let’s look at the actual mechanic of asking.

How to ask a guy out over text

Texting is a great, low-pressure idea, if you’re not sure how to ask a man out. It has the advantage of not putting your crush on the spot and giving him time to craft a graceful out if he’s not interested. Some tips:

Be direct

Everyone appreciates someone who knows what they want. Often, the best way to ask someone out, even over text, is to just put it out there: ‘Hey, would you like to have dinner on Thursday? I know a great Mexican place.’ or ‘Hey, [that band you like] is playing at [local venue], want to go together?’ is much better than, ‘Hey, want to hang out sometime?’

Make it personal

Tone can be really hard to read in text, so make sure your message is tailored to him. Don’t just randomly text out of the blue to ask for a date; chat a little beforehand to get things rolling and let him know you want to see him in person.

Play off a common interest

Do you like similar bands? Art aficionados? In the middle of a fierce competition over who can eat the hottest chilli? Take advantage of that when you’re asking a man out – it’s much more likely to lead to a ‘yes’ than a generic invitation to ‘do something together.’

Leave room for a ‘no’

Nobody likes being cornered so make sure he has a way of saying no if that’s what he wants. An easy way to do this is to ask if he’s busy this week. If he says yes more than once? It’s a signal he’s just not that into you.

How to ask a guy out in person

Sometimes, it just so happens that the best way to ask for a date is face-to-face. Here’s some advice for how to ask a guy out without getting rejected.

Pick a time and place you’re comfortable

Maybe it’s during a party you’re both at, or when you’re all out with friends, or doing something together (though make sure you have an escape route in case you don’t get the answer you want). Being comfortable will show in how confident you are, and men love confidence.

Practice makes perfect

It sounds corny but we’re serious. Practising asking a guy out with a friend or by yourself in front of a mirror is a great way to overcome any shyness you might feel. Practising your lines is a great way to build confidence for when you actually ask.

Just ask!

Sometimes you have to just do it. Start off with a smile and compliment, and then ask, simple and clear, ‘Hey, would you like to have dinner sometime?’ or ‘Would you like to go on a date with me?’ Any guy would be flattered by the expression of interest..

Creative ways to ask a guy out

We’ve covered the more straightforward ways you can go about it. Now let’s look at tips for asking a guy out that don’t require as much boldness.

Get a friend in on it

There’s no shame in using a wingwoman or man. You’re still taking control. Ask one of your friends who knows him – ideally a mutual friend – to talk up your best qualities and softly prod him for information on how he sees you. It will also subtly betray your interest, but in a good way. 

Be silly and self-aware about it

This one does require an approach but it’s a humorous one. You are sort of flipping the gender roles so be satirical about it to diffuse any tension. Open with a cheesy pickup line like, “Do you believe in love at first sight—or should I walk by again?” Or if you’re in a bar, have the waiter send him over a cocktail from you. 

Get old-school and make him a mix tape

This is a good option if you’re trying to figure out how to ask a guy out without directly asking. While a cassette or CD would be cute and retro, players are becoming rarer. So go more laid back with it and share a Spotify playlist –and make sure the cover photo for the playlist also hints at your interest.

How to ask a guy out sneakily

While we’d never endorse outright dishonesty in dating, there’s nothing wrong with being crafty. Acting like he’s doing you a favor by taking you up on a spare ticket you have because “friends dropped out” or asking for his help with something and “thanking him” by taking him to lunch are creative ways to ask a guy out without being too direct. 

How to ask a man out: seize the date!

It’s a common refrain – aren’t you afraid you’ll intimidate a man by asking him out? Well, then maybe he’s not the right guy for you. You should be confident in your decision to ask him out. Sign up for eharmony and get started on meeting your perfect guy today.

FAQ

What’s a good way to ask a guy out?

There are a lot of effective ways one might explore when asking a man out but tailor your approach to the guy, as different personalities will respond quite distinctly.

If we were to sum up the most efficient and simple method, we’d say be forward, friendly and purposeful.

How to ask a guy out without being awkward?

While it’s easy to tell you to just be confident, we understand that’s easier said than done. Making the situation less loaded feels less awkward– so work up to it organically while feeling out the vibe. Going out might just end up becoming something you mutually come up with.

Is it desperate to ask a guy out?

No. You’re ignoring outdated gender roles, claiming agency over your love life and expressing the inspiring confidence it takes to be the one to initiate romantic interactions. Does that person sound desperate to you? It sounds more like they have something figured out the rest of us don’t.   

How do I handle rejection when asking a guy out?

Rejection is a downside of shifting the paradigm. It feels counterintuitive but don’t take it personally. There could be so many reasons they said ‘no’ that don’t involve you. But it’s important to accept their answer. It’s okay to say you’re disappointed but stay friendly and make a graceful exit.