How to Ask Someone Out: Tips for a Confident and Memorable Approach

Asking someone out is always low-key stressful. 

Regardless if you’re doing it in person or via an online dating site, your palms get sweaty, the pulse rate goes up, and you’re praying to the Gods of dating that the person on the other side doesn’t reject you. 

At the same time, the thrill that you feel in the process, and the endorphin boost you get when they say Yes is one of a kind. 

The Art of Asking Someone Out 

How do you ask someone out and not feel weak in the knees? 

The Once team has yet to learn this magical trick. Yet, we’re here to discuss all things asking-someone-out. Let’s dive deeper into the topic and understand why it makes us so stressed, what’s important in this process, and the common misconceptions we hear and see about asking someone out on a date. 

Why asking someone out can feel intimidating 

Many factors go into asking someone out. First, you’re afraid of rejection. If there’s one thing humans absolutely hate, it’s being rejected. Unsuccessful attempts to ask a person on a date can snowball into a huge mix of insecurity, anxiety, and self-doubt. Not something we want to experience, right? 

Then there is the vulnerability of opening up to someone about your intimate feelings. You’re putting yourself on the line and admitting you like someone. It’s generally an uncomfortable thing to do unless you’re super-duper self-assured and confident. 

There is also the social pressure. What if someone finds out that you were rejected and starts talking behind your back? Even the thought of that is sad. 

Lastly, it’s simply stressful to face uncertainty and not know what the other person will say. 

The importance of confidence and authenticity 

The truth is that you never know what the other person will tell you when you ask them out. You can have all those ideas, perceptions, and predictions in your head, but the answer will be unpredictable. Similarly, you may hesitate for days and weeks, only to learn that your love interest is dying for you to ask them out. 

The best thing you can do is be confident and authentic. If the first one is hard for you, focus on authenticity. Tell them how you feel and why you want to take them someplace nice. Don’t play any games or pretend to be someone you’re not. Honesty is the best policy, and it’s your best bet in getting that date. 

Common misconceptions about asking someone on a date 

Here are a number of things you don’t need to worry about when asking someone out, despite what society wants you to believe.

1. You don’t need to find the perfect time to ask someone out. The only thing you need is to not ask them at the obviously wrong time, but that’s about it. 
2. There’s absolutely no need to come up with a perfect line, especially a perfect pickup line. 
3. You’re not unworthy if you’re rejected. Not everyone reciprocates your feelings and that’s alright. It may hurt in the moment, but once the time goes by you’ll be happy that the person didn’t say Yes for the wrong reasons. 
4. The other person won’t be annoyed if you ask them out. Sometimes we don’t share our feelings with others because we fear that it will bother them. However, if you’re not being weird about it, it’s perfectly fine to ask someone on a date. As long as you’re respectful and don’t push their boundaries – nobody will be annoyed. Real life is not a Mean Girls movie.
5. You can ask them out even if you don’t know how they feel about you. Another very common misconception is that you must be sure the sympathy is mutual before going ahead. That’s simply not true. Unless you get the bad vibes from them, just ask them out. 

How to Prepare Before Asking Someone Out 

Before you pop the question, make sure that you do the homework to boost your chances of a positive outcome. 

Identify your intentions and what you’re looking for

Do this not just for you but also for the person you’re about to ask out. The last thing you want and need is to waste your time and the time of your date. Mindful dating starts with the right intention. Think about what you want out of this date to plan accordingly. For example, if you want to date someone seriously, texting them at 1 am on a Saturday night asking ‘WYD’ and if they want to hang out is not the right move. 

Choose the right time and approach 

As with our example above, your intentions will identify how and when you ask someone out. Make sure you’re considerate and don’t drop the big question on the person at the least comfortable moment. 

For example, if your crush is visibly stressed and juggles multiple things at once, asking them out at this moment will probably lead to confusion and maybe even irritation. Also, it’s not a good move to ask someone on a date in front of other people. First, this puts them in an incredibly awkward position. Second, they might say Yes just to get out of this situation and not have people stare at them. Is that something you want? 

Observe verbal and non-verbal cues to gauge interest 

Before you decide to ask them out, do a little bit of fieldwork and estimate your success chances. 

Is the person even interested in you? If you’re into women, many of them will be polite and friendly which men can mistake for flirting. Watch out for how they talk to you, things they share or keep hidden, whether they’re making jokes and complimenting you, or if they’re trying to be closer to you and touch you (if you’re seeing them offline). 

It can be heartbreaking sometimes to have an honest look and see the other person not being interested in you. It’s much better though to come to this realization on your own, and not once you ask them to dinner and they say No. 

Best Ways to Ask a Girl Out 

Here is how to ask a girl out and improve your chances of getting a Yes. 

Approach her directly and be clear with your invitation

For example, say that you’re interested in a date and want to do this or that. Avoid fishing for her plans or making ambiguous suggestions, such as “Maybe we can hang out sometime”. This kind of approach is not impressing anyone. 

Don’t put too much stress on it, but don’t let her feel like you don’t care either. Balance is key. Tell her straight up what you want, and say that it would make you really happy if she accepts your invitation. 

Also, you can add that there is no pressure for her to agree, and it’s fine if she says No. Best to mention it if you see some hesitation in her face. Note that if you say it right after the invite without a break to breathe, this may devalue your invite a little bit. So take a pause, and only then speak more. 

Delivery matters a lot. How confident you are, whether you respect her boundaries or not, if your invite feels personal and genuine, or as something that you tell every other woman you meet. 

Be specific with your plans

The best way to ask a girl on a date is to take control and make plans. If a man asks a woman out and then leaves it to her to decide where to go, what to do, and when to meet.. Well, let’s just say, it’s not the hottest behavior out there. 

Don’t be that guy. Instead:

• Suggest a time, a place, and an activity for your date.
• Have a plan B if she doesn’t fancy your primary idea. 
• Be flexible with timing. Unless you know what time works for her, give her alternative options. 
• Be mindful with planning – no extreme sports, dates in the middle of nowhere where she might feel unsafe, or activities that you know she doesn’t care about. 

Deal with rejections gracefully

There’s nothing worse (and, frankly, pathetic) than dealing with a man who throws a tantrum when a girl doesn’t want to go out with him. Trust us, all women share those horror stories with each other, laugh, joke, and judge. And they have all the right to do it! 

Rejections suck, but nobody owes you their time and affection, so don’t make it weird. Not only can you make a woman feel unsafe if you get angry or insistent, but you’ll also ruin your reputation forever. Word travels fast, and you don’t want to ruin your future chances with someone else just because you can’t handle a rejection like an adult. 

The best approach to dealing with a No is to smile, thank her for being honest, suggest that the offer stands if she changes her mind (if you’re up for it, of course), and leave it at that. 

The key principles

While you’re wondering how to ask a girl out, remember that you need to follow a few simple rules. They are timeless and necessary if you want it to be a positive experience for everyone.

1. Respect her answer, whatever it is. 
2. Be specific with your plans.
3. State your intentions clearly. 
4. Be positive, even when rejected. 
5. Take No for an answer, don’t insist. 

Creative ways to ask someone out over text 

• Try humor and an inside joke that only you two would understand.
• Add a cute picture or sticker to your text.
• Text them in a making-a-doctor-appointment fashion but make it absurd, so the other person understands you’re not using this tone seriously.
• Record a short video invite and send it to your crush. 

Questions to Ask Someone on a Date 

So you got a date, congrats! Here are a couple of questions you can ask to get the ball rolling. You’ll probably find things to ask yourself, but our examples will help if you get a brain freeze from excitement.

• What is your ultimate dream travel destination?
• What do you cook for yourself when you need a little pick-me-up?
• What is your favorite way to spend the weekend?
• If you could redo my style, what would you change?
• How do you feel about the sudden boom of running clubs?
• Are you more into books or movies?
• Would you say you’re happy with your career path right now?
• Many people hate walking and coffee dates. What about you?
• Have you ever lived abroad? 
• Where would you like to live, besides the country you’re in right now?

The key to questions is to make them seem natural. You’re not interrogating your date, but rather having a naturally flowing conversation where you get to know each other better. 

Also, make sure the questions you ask and the topics you bring up are a mix of fun, light-hearted ones and meaningful and serious. Dates are supposed to be both! You need to understand if you match with the person but also have a good time with them. Mix the two and you’ll have an enjoyable time together. 

Asking Someone Out FAQ

How do you ask someone on a date over text without sounding nervous?

The biggest giveaway is overthinking. Overthinking manifests in too many words used or the text being too stale and feeling overly “curated”. Try to sound natural and include the key points: you like this person, you want to meet them to get to know them better, and here is the idea of the time and place. 

Anything extra will probably give out your nervousness which is, by the way, not the worst thing in the world. You being anxious about asking someone out is actually sweet. The person you fancy will see that you’re really into them and appreciate it.

Can you share examples of cute asking-out texts?

There are plenty of cute asking-out texts you can find online, but we don’t encourage you to copy someone’s style. If you do, make sure you adapt it to your situation or it will feel disingenuous. 

So, how do you ask someone out in a cute way? Here are a couple of ideas to get you started:

• If I asked you to dinner next Friday at a new Italian place, what would your hypothetical answer be? Asking for a friend.
• You like bubble tea, right? This new spot just opened. I’d like to treat you, plus we can have a walk in the park next to it, and maybe grab something to eat later?
• I’ve spent the last 2 hours unsuccessfully brainstorming how to ask you out, and all my ideas seemed cringe. I really like you and want to get to know you, what do you say about a date this weekend?