How to Ask Someone Out on a Date

Learning how to ask someone out can make all the difference in your online and offline romances! And it’s not as hard as you might think. With these simple changes, you’ll never let another opportunity pass you by!

How to ask someone out online

These days, most of us land our first dates from dating websites. But, that doesn’t mean that asking someone out on an app is easy! Here are a few ways that you can move your chemistry offline:

Build rapport

We know that online dating can sometimes feel a bit two-dimensional, and that can make you feel eager to get to the in-person part. But you still shouldn’t rush the getting-to-know-you phase. These early interactions are when you can start building trust, exploring your chemistry, and making a good impression. If you’re not sure how to do that, try out a few online dating icebreaker questions to get the ball rolling.

Make your date proposal personal

When you are ready to take things offline or to a video call, make sure that you stay away from cut & paste pick-up lines. You know the ones: “I’d like to take you to the movies but they have a rule against bringing in your own snacks.” A cookie-cutter response like this may get a quick laugh but it will feel impersonal and careless—and honestly a bit cringe—which will increase your chances for rejection.

Instead, make it personal and specific. For instance, if you’ve already chatted about your shared love of wine or they’re holding a wine glass in their profile picture, you might say something like, “I’d love for you to teach me more about wine sometime. They just opened up a new wine bar in my neighborhood, actually. Would you like to check it out with me sometime?”

Schedule something quickly

If you received a yes, congratulations! Now it’s time to actually get something in the calendar. Otherwise, you may lose the momentum and never make it happen! So make sure that before the conversation is over, you offer some possible dates and times.

How to ask someone out that you’ve just met

Not all dates come from the internet these days. And if you see someone out in the real world who looks interesting, don’t hesitate to make a connection! Here’s how:

Make sure they’re open to being approached

Someone who is talking on the phone, has headphones in, or generally looks unavailable may not react well to being asked out. So make sure that you read their body language before approaching.

Start off with small talk

As much as you may hate small talk with your coworkers, it can be useful in striking up a conversation with a stranger! Small talk makes people feel comfortable and can give you the chance to gauge whether they’re open to connecting or not. Here are a few tips for better small talk:

• Smile. Relax the muscles in your face, lower your shoulders, and smile!
• Make a joke. If humor comes naturally to you, try cracking a joke! Making someone laugh is an instant way to start building rapport with them.
• Ask a question, a favor, or a recommendation. If jokes aren’t your strong suit, try a different method instead. Asking for a very small favor, like whether they know where the restroom is or the wifi password, can be the start of a conversation.
• Be honest. Sometimes, a genuine compliment can be the secret of how to ask someone out successfully! For instance, you might say something like, “You look like a really interesting person, and I wonder if we could exchange numbers or if I could get your Instagram?” or “Sorry to interrupt but I’ve been trying to build up the courage to ask whether you’re single.” Being vulnerable in this way can be endearing and appealing to someone you’ve just met. So, don’t be afraid to get out of your comfort zone!

How to ask someone out that you know

Asking out your barista, someone who lives in your neighborhood, or an acquaintance from the dog park can feel even more intimidating than asking out a stranger! After all, if they say no, you’ll need to find a way to continue seeing them without things being weird. Here’s how you can broach the subject with class:

Be honest about your feelings

Whenever you’re asking out someone you already know, there’s a chance that they’ll assume you’re asking them non-romantically. So, clarify your feelings. You might say something like, “You know, it really brightens my day when I see you. Would you be interested in going on a date sometime?”

Ask them to do something you know they’ll enjoy

Since you know this person a bit, you might have a better idea of what they’d like to do on a date. So, make your proposal specific to boost your chances that they’ll say yes.

Let them know that you don’t want to make things weird between the two of you

The person you’re asking may be hesitant to go on a date. Because, as we said, if it doesn’t go well, you’ll have to continue seeing each other. You can alleviate their worry by naming the fear and stating your intention to keep things positive. Try something like, “I understand if you’re worried about things being awkward between us. I’m a little worried about that too. But, we get along really well, and even if you decide you don’t want to see me again, I think we can go back to being friends.” When you show that you can be emotionally mature about the situation, you’re more likely to get a positive response!

Universal tips for asking someone out

No matter whether you’ve swiped right online, met in person, or known each other for a while, there are a few universal tricks that can make the asking process more successful!

Don’t say no to yourself before they do

The worst thing you can do when learning how to ask someone out is assume they’re going to say no. This will make you feel nervous and unsure, and that insecurity will make the interaction awkward. Working on your confidence is, of course, a process. But, try hyping yourself up with affirmations, such as “They’ll say yes!” or “I have a lot to offer!”

Don’t wait too long

Maybe you’ve run into this person many times and still haven’t built up the courage to ask them out. This is understandable. But the longer you wait, the harder it will be to jump over that emotional barrier! So, even if you’re nervous, just go for it before you have too much time to psych yourself out.

If you get a no, don’t try again

You deserve to date people who are enthusiastic to get to know you better. So, if you get a no, don’t push it. After all, you don’t want to waste your time and energy on someone who isn’t interested when you could be asking other people out!

If you get a no, don’t give up on dating altogether

Being rejected is hard, but try to remember that there are many reasons why someone might say no. And many of them have nothing to do with you. You might have asked out someone who isn’t ready to date, is too busy for a relationship, or knows that they wouldn’t be a good partner for you. So, don’t get discouraged. There’s someone else out there for you!

If you get a yes, follow up

If you do get a yes, congratulations! Now it’s time to make sure that you stay connected from now until your date. Don’t bombard them with messages, of course. But, you can send a message a couple of days or a day before the date to confirm.

There are many tactics for how to ask someone out. How will you try?

Ultimately, the best way to ask someone out is however you feel the most comfortable. So, try a few of these tips but make sure that you follow your own intuition, too. That will make it easier for you to build connections and land that much-anticipated “yes!”

Good luck!