How To Ask Someone Out If You’re Shy

6 expert tips to give you confidence

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Dating today can seem pretty discouraging if you’re not getting anywhere with anyone. But if you really want to transform your love life, it might be time to stop waiting for that certain someone to take notice and ask you out. Instead, take control of your dating life and just ask them out yourself!

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“Making the first move gives you the opportunity to stand out from the ‘norm,’” says Anna F. Wood, dating expert and founder of feminist lifestyle platform Brains over Blonde. “Don’t be generic, add some humor, and keep it simple — you may be pleasantly surprised.”

When you’re shy, that’s easier said than done. The good news is, it’s not impossible. So here’s what you can do to ask someone out if you’re shy.

1. Downplay it in your head

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“Stop concentrating on the fact that you’re asking someone out on a date,” Stacii Jae Johnson, dating coach and founder of The Single Girls Club Conference, tells AwesomenessTV. “Instead, just think of it as asking a friend to go hang out with you.”

Sure, asking to hang out with someone you find attractive is obviously not the same as asking your close friend to grab lunch after class. But if approaching someone for a “date” makes you super nervous, try to downplay it in your head. It will lessen the amount of pressure you may be putting on yourself.

2. Do some background prep work and build a connection

If you’re shy and reluctant to ask someone out, Johnson says, preparation is key. “You want to learn something about them that you are genuinely interested in. Whether it is a hobby they have, a place they have visited, [or] a favorite subject or food.”

In this case, social media will be your friend. “Look at their Twitter, Instagram, or Pinterest page to see what they’re posting,” Johnson says. “Find a commonality. Let [the] interest you share be the starting point for the conversation, talk a bit, and then ask if they want to continue the conversation sometime over coffee or lunch.”

It’s all about building a connection between you and the person you’re interested in before you ask them out on a date.

3. Have a simple set “script” prepared

Here’s some advice for anyone dating online: If you’re on a dating app and you’re ready to take things IRL, have a simple line ready that you can tailor to each person. For example, you can say, “Hey, we could keep talking on the app about (insert topic here), but I’d rather do this in person. What do you think?”

“This line is simple, easy, and can be used in multiple scenarios and with multiple people,” Sarah-Rose Marcus, an online dating strategist, tells AwesomenessTV. “In today’s society it is much more common to chat back and forth for an amount of time before meeting in person. Keep it short. You don’t want a pen pal.”

4. Ask your friends for an intro

One of the best ways to meet new people is through friends. If your friend happens to know your crush, ask them for an intro and even tell them to put in a good word for you.

Just to be clear, you should never give your friend the task of asking someone out for you. But there’s nothing wrong with asking your friend to drop little hints for you here and there.

5. Think of a fun activity to do on your date

If the idea of asking them out for a formal dinner date makes you too nervous, then don’t. As Erika Kaplan, a matchmaker with Three Day Rule, says, go for the activity date. “Ask to do an activity on the first date that involves less one-on-one talking,” Kaplan says. “That way you can make conversation around what you are doing, rather than having to feel like you are being interviewed.”

Not everyone is comfortable going out to dinner with someone they’re just getting to know. Asking someone out for dinner can make it seem like a bigger deal than it has to be. But if you think of something more fun to invite them to, they’re more likely to say yes.

6. Use technology to your advantage

“Use technology as your way in,” says Rori Sassoon, relationship expert and CEO of matchmaking service Platinum Poire. “If you have mutual friends on an app, you can wink at them or slide into their direct messages with a sincere and sweet compliment.”

Find a way to start a conversation with them online, whether it’s about a recent IG post or a mutual friend. And these days, texting someone to ask them out is perfectly acceptable, especially when you’re shy.

Kristine Fellizar
Kristine Fellizar

Kristine Fellizar is a writer and editor based in Los Angeles. She specializes in everything related to sex, dating, and relationships. When she’s not working and feeding into her coffee and boba addiction all over L.A., chances are you'll find her at Disneyland.