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19 Cute & Flirty Ways to Ask Someone Out & Make Them Feel Special

If you know them already and are looking for really cute or flirty ways to ask someone out, give these a try to make them smile and say yes!

how to ask someone out

If you are thinking about how to ask someone out in a cute or flirty way, you want to prepare a little. Just running up to someone and shouting “WILL YOU GO OUT WITH ME?!?” into their face is unlikely to get you the desired response.

People like to feel special. They want to feel secure, and they appreciate it when someone makes them feel desired and wanted.

Do all of this when you’re asking someone out, and they are much more likely to say yes.

Of course, it’s always a good idea to have a plan in mind of what to do if they say yes or no. If you get the response you hope for, try to keep it casual and make sure you set it up, so you’ve got their number or plan arrangements then and there.

Similarly, if they say no, be cool. Don’t get annoyed or burst into tears. Everyone gets rejected from time to time. Just remember that there are plenty more fish in the sea.

Not sure if they like you back? Use this guide if you want to know how to ask someone out over text or in person and win their heart.

Believe in yourself—whatever the answer

Before you go for it, try to keep calm. While you might have had a crush for what feels like forever and built up the courage to do it, just remember that asking someone out on a date should be a casual thing.

You aren’t asking them for a limb or to marry you. Try to keep things in perspective. Acting cool, calm, and collected shows your confidence—and that itself is really attractive.

Believe in yourself too! Visualizing them saying yes or imagining the two of you having a great time on your first date helps. If you feel shaky, timid, or uncertain, this comes across and has a negative effect.

[Read: 15 easy ways to tell if someone likes you without asking them directly]

How to ask someone out

When you are ready to go for it, make sure you are clear and specific. It can be easy to beat around the bush or ask them in a way that you can pretend that’s not really what you were doing if they say no. That’s really just the coward’s way out!

If you are too vague, it makes your potential date feel nervous. Also, they might say yes without knowing what they are saying yes to, only to decline the offer later when they find out.

Learn how to ask someone out the right way and save yourself the disappointment—make it clear that it’s a date and that it will be just the two of you.

Now that you feel confident and ready, just what are the best ways to ask someone out? Here are great ways to ask someone out. [Read: How to ask someone out over text]

1. Write them a note

If you want to be cute, why not ask them out by passing them a handwritten note? This could be on the back of a napkin in a coffee shop or passed to them via friends.

It takes it back to an old-school, classroom kind of vibe and is sure to charm them right away. [Read: How to ask a friend out without risking the friendship]

2. Smile at them

There is nothing quite as lovely as someone giving you a huge smile. If you are not feeling confident about asking someone out, why not see if you catch their eye and then deliver them a fantastic, beaming smile.

If you do this and they smile right back at you, you know you are onto something and should consider biting the bullet and going up to them to ask them on a proper date.

3. Buy them a drink

Again, if you want to use tried and tested methods, then offering to buy someone a drink or having a drink sent over is a great way to initiate the conversation that leads to you asking someone on a date.

If the person you are interested in is interested too, they’ll undoubtedly thank you or invite you to join them. [Read: How to approach women – 15 tips you absolutely need to know]

4. Pay for their coffee

Coffee shops are a great place to hang out, but do you know how to ask someone out, out of the blue? For starters, if you spot a cute guy or girl in line at a coffee store, why not offer to pay for their coffee?

This way, you get talking to them, and you’ve already bought them their very first gift! They’ll know you are interested right away, and if they feel the same way, they’ll no doubt accept.

5. Send them a text

If you feel particularly nervous about asking this person out, you don’t always have to do it face to face. It can be scary if you aren’t sure whether that person will say yes or not, and the horrible pause where you might get rejected is sometimes too much to bear!

This is understandable. If you aren’t sure and you’ve got their number take all the pressure off by coming up with a cute and funny text to send them instead! *Warning: It doesn’t make the waiting any easier, though!* [Read: Texting your crush: A step-by-step guide to doing it right]

6. Videochat

If you aren’t in person but don’t want to ask them out over text because it seems impersonal this is the perfect balance.

Videochat and ask them so you see their genuine reaction. If you text them and let them know you’re about to facetime them, hold up a sign that says, “Will you go out with me?”

This will catch them off guard but is also super sweet.

7. Buy them flowers

Everyone loves to feel special. A lovely bunch of bright blooms brings cheer to anyone’s day. Buying or sending them flowers makes them feel special and flattered—you are more likely to get that big fat, yes!

8. Surprise them

Show up somewhere they wouldn’t expect to see you *in a non-stalker way, obviously* and surprise them by asking them on a date then and there!

9. Plan a whole day

Make sure you know how much effort you put into it and how much you like them by asking them to come on a whole special date day with you.

Have an excellent plan in place that is sure to impress them if they ask for more details! [Read: Top 50 amazing first date ideas to wow your date]

10. Ask where they are from

Another simple ice-breaker that helps you out if you are about to ask out a total stranger. Casual conversation starters are sometimes the best way to get the vibes on whether a person has reciprocal feelings, so if you worry about rejection, this might be the way to go. [Read: Approach anxiety – 16 effortless ways to conquer it in a few days]

11. Ask what they are reading

Like that cute girl sitting and reading on a bench? Ask her to tell you about the book she is reading. Another easy way to get the conversation going.

12. Compliment them

Everyone likes to be flattered and feel beautiful, so giving your potential date a fabulous compliment immediately makes them feel special and way more likely to say yes.

13. Find something in common with them

People are more likely to say yes to dates that they think they will enjoy. Try to find out what you have in common with the person you hope to date before asking them out. This way, you plan and suggest something that you know they’ll be interested in. [Read: How to start a conversation with a crush and woo them]

14. Find out their favorite food or restaurant

Find out what they like to eat and either suggest that you take them to their favorite restaurant or cook them a home-cooked meal full of all their most loved dishes!

15. Ask them for the time

Wondering how to ask someone out when you bump into them on the street? Ask them for the time. It just gets the conversation started, and if they look like they aren’t interested, then you haven’t put yourself out there too much. It’s a win-win! If you get a smile and their body language is positive, you simply take it from there. [Read: How to be flirty while maintaining class and poise]

16. Ask about their dream date

Ask them what their ideal date is and then make it come true. When they explain say, “I think I can make that happen.” How can they turn that down?

17. Play a game

Play a word game like Hangman. Have them try to figure out the phrase. It will be “Will you go out with me?” They’ll have to say yes just for the creativity factor. [Read: A gentleman’s way to ask a woman out]

18. See if they like you

When you want to ask someone out you are always nervous about being rejected. That is part of the risk when it comes to dating.

But, if you don’t want to ask without at least thinking you know their answer, feel them out. Don’t feel them up!

Flirt with them. Do they flirt back? Do they ask you about your dating life? Are they trying to get to know you better?

19. Pay attention

Learn more about them. Whether you are friends or just met, pay attention to what they talk about and ask them to do something you know they’ll enjoy.

If they love sports ask them to see a game. If they love music go to an open mic night or record store. Ask them on a specific date they’ll enjoy so they are more likely to say yes. [Read: 10 ways to be a better listener]

20. Be unique

Do something out of the box when you ask someone out. Play a game of basketball and if you win you get to take them on a date and if they win they get to take you. Try to come up with something memorable.

21. Keep in PG

Do not touch them. Just keep your hands to yourself. You’reaskign them on a date, not to get married. Slow it down.

Sure, you want them to know it is a date and not just a platonic get-together but you can do that by saying it, not touching them without consent.

22. Be yourself

Be genuine when you ask someone out. Even if you want to take them to a baseball game because they love it, don’t pretend you love it if you don’t. Let them know you’re excited to learn more about the sport or see them get into the competition.

Don’t pretend to be someone you’re not just to get someone to go out with you. Be yourself, they will find out you lied anyway. You might as well be truthful from the start. [Read: Be yourself: 14 steps to unfake your life]

23. See them as an equal

Sometimes when asking someone out you can psych yourself out. you think they are out of your league or will surely say no. that will only throw you off and make you unsure.

Instead, view them as a person. If you see them as perfect or too pretty or too hot, you’ll be in awe of them and it will put a lot of pressure on them to live up to that expectation.

24. Respect them

Whether they say yes or no or maybe always be respectful. Not only will they appreciate it and be more likely to agree to a date, but when you are rejected and handle it well with poise and grace, you are showing what a good person you are. Word tends to get around if you react poorly to rejection or worse, try to change their mind. [Read: How to set personal boundaries]

25. Be straight forward

When you want to know how to ask someone out, just do it. Don’t overthink it. That can make some people extra nervous. you don’t need to plan something out or be super romantic.

Sometimes just saying, “I like you. Would you want to go out this weekend?” is perfect.

26. Let them ask you out

Why do it yourself when they could ask you out? Hint to them about a new restaurant you’ve been dying to try or mention a movie that looks good. They will get the message and you won’t have to worry about being rejected.

[Read: 15 ways to tell if someone likes you without asking them]

So there you have it, now that you know how to ask someone out, be it a friend or a total stranger, which move will you pick?!

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The editorial team of LovePanky comprises relationship experts and real-life experts that share their experiences and life lessons. If you want the best love ad...