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How To Ask Someone On A Date Without Actually Psyching Yourself Out

How to Ask Someone on a Date
PHOTO: RyanKing999/Getty Images

Whether you’re getting the cold sweats just thinking about approaching your crush or you’re stressing over crafting the perfect dating app opening line, you know that asking someone out can be stressful as hell. Like, we’re weren’t exactly taught how to ask someone out in school (lol) and most standard pick up lines can come off cliché and maybe a little corny when said out loud.

That leaves us with basically no playbook, so it’s no wonder you might be second guessing yourself when it comes to shooting your shot. Lucky for you, we tapped relationship experts to help figure it out.

First thing’s first: You should know that it’s not uncommon to experience fear and uncertainty when asking someone out, explains sex therapist Janet Brito, PhD, founder of the Hawaii Center for Sexual and Relationship Health. It’s an act of vulnerability, after all, and there’s no way to predict what their answer will be—but don’t let the fear of “rejection” stop you.

Instead, work towards approaching a prospective date in “a confident way that conveys you want to get to know them,” Brito explains. You don’t necessarily have to seem cool and calm, but rather, “let your personality shine through and be kind,” says Brito.

If that sounds way easier said than done, worry not. The following is your expert-backed, step-by-step guide for how to ask someone out. (And yup, we’re covering IRL conversations, text messages, dating app approaches, and more.)


First, Identify Your Intentions

Before you ask someone out, be mindful and ask yourself what your intentions are in doing so, says Brito. Identify your goal. Are you asking them out because you’re authentically curious about them? Do you want to get to know them? It’s important to know the answer before acting, says Brito.

If you’re just trying to hook up or use them to get over someone else, then be clear with your intentions from the jump and tell them you’re not looking for something serious. It will ensure that everyone’s expectations are aligned and no one gets hurt in the process.

Notice What’s Unique to Them.

“Whether you’re online or in the supermarket, I always tell my single clients to notice something out of the box about the other person that they are showcasing,” explains sex therapist Jenni Skyler, PhD, director of The Intimacy Institute. Speak to that feature as your point of entry into the conversation. For example, you can approach someone and say something like, “Hey, I noticed that you’re wearing a t-shirt from X sandwich shop. Do you go there often?” A confident curiosity is going to take you far, says Skyler.

The same advice goes for when you’re chatting on dating apps. “People put pictures on their profiles and you can speak to the uniqueness of a picture as a first point of contact,” Skyler explains. If someone has photos of dogs in their profile, for example, you can comment on those, but def try to be as creative as possible.

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“Most people are going to go for the obvious, low-hanging fruit. Try to set yourself apart and notice the little things,” Skyler says. But again, whether it's IRL or online, just saying, “Hey. I noticed this about you and would love to hear more,” can be super helpful.

Be Specific, Please!

“Mystery is fun, but you also want to know what you're signing up for with a stranger,” Skyler explains. When you ask someone out, make sure you’re specifying what you’re asking them out for and, as mentioned, make your intentions clear. “A lot of people will just ask for a number and there's no specificity,” says Skyler, which can obscure your reason for interest.

Differentiate yourself from other people and let this person know that you’re intentionally asking them out on a date, and throw out some suggestions for what you might want to do, says Skyler. You could say, “I'd love to go for a walk or a drink.” Or dinner. Or coffee. The options are endless—but suggest something that suits your personality and gauge what this new person might enjoy as well.

~Get a Feel~ For the Group Dynamic.

It generally feels a lot less daunting to approach someone when they’re alone. But what if the person you want to ask out is surrounded by a group of friends? “If there are group dynamics, you might need to socialize a little bit with the group,” says Skyler. Be polite to everyone there, but also don’t be afraid to give a little bit of extra attention to the person you want to ask out, too, Skyler explains. (Maybe they’ll get the hint!)


Once you’ve mingled with the group, you can ask the person you’re interested in to chat individually. “I wouldn't ask somebody out in front of all their friends,” says Skyler. Instead, say, “Can I ask you a question over here?” And see if they’re okay to step aside. If you’re worried about making them uncomfortable, you can always make sure they’re still physically close and visible to their friends.

Be Respectful of the Answer You Receive.

Whether they’re interested or not, be respectful of the decision this person makes—no matter how you feel. “If they’re not interested, that’s okay. It’s not personal to you, and you don’t need to put yourself down,” Brito explains. Regardless of what they say (unless they purposefully insult you!), it’s not a reason to be mean, says Brito.

Instead, wish them the best even when you get an answer you don’t want, she says. It’s polite! And if you received a yes? Good for you—time to start planning the big date. Fingers cross—you've totally got this.


This article originally appeared on Minor edits have been made by the editors.

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