How To Ask A Guy Out? 21 Creative Ideas To Set You Up For Success

Dating experience | | , Intimacy & Relationship Writer
Updated On: December 7, 2023
how to ask a guy out

Ask yourself, should you ask a guy out? If you’re struggling with how to ask a guy out, you’re not alone. Many women find themselves in this position, wondering how to make the first move without feeling awkward or rejected. So, if you’re wondering how to ask your crush out, then this article is for you.

Fortunately, there are plenty of cheesy ways to ask a guy out. There are also many creative ideas and strategies you can try to increase your chances of success, from playful and flirtatious to direct and straightforward. Learn how to ask a guy out without getting rejected, as there’s an approach out there that’s sure to suit your personality and situation.

In this article, we’ll explore 21 different ideas for asking a guy out, ranging from classic and traditional to unconventional and unexpected, and teach you how to ask your crush out. Whether you’re interested in a coworker, a friend, or someone you just met, these few tips will give you the confidence and inspiration you need to take the plunge and ask him out on a date. So, take a deep breath, and let’s get started!

How To Ask A Guy Out? 21 Creative Ideas To Try

Asking a guy out can be nerve-wracking, but it doesn’t have to be. So ditch the common dating practices and with a little creativity and courage, you can make a lasting impression and find your perfect guy. In this article, we’ll explore 21 creative ideas to help you ask a guy out. Whether you’re looking for a stress-free way to get to know someone or want to make a grand gesture, there’s something here for everyone. Let’s hope things go great and you end up googling hangout ideas with a guy. So, get ready to step out of your comfort zone and take charge of your dating life with these cute ways to ask a guy out:

1. Use a scavenger hunt

A scavenger hunt is a fun and creative way to ask a guy out. To create a scavenger hunt, start by thinking of places in your neighborhood that are significant to you or the guy you’re interested in. You could use a park, a coffee shop, or a favorite restaurant. Then, create clues that lead the guy from one location to the next. You could leave notes or small gifts at each location that provide hints for the next step. Make sure the final clue leads to you, where you’ll be waiting with a romantic invitation to go out on a date.

Organizing a romantic scavenger hunt can be a fun and unforgettable way of asking a guy out. How to set one up? Read on!

  • Know his interests: Consider the guy’s hobbies, interests, and favorite places. Tailor the scavenger hunt around things that are significant to him, making it more personal and enjoyable
  • Choose the locations: Choose a few locations in your neighborhood that have sentimental value or are related to his interests. They could be places where you’ve had great conversations and shared memories. You can also choose spots he likes.

Related Reading: What Does It Mean When A Guy Says ‘I Am Not Good Enough For You’?

  • Make clues: Write clues that will lead the guy from one location to the next. Each clue should be challenging enough and should require some thought but should not be so difficult that he gets frustrated. Incorporate inside jokes or references that only he would understand, to add a personal touch
  • Hide notes or gifts: At each location, leave a note or a small gift that contains the next clue. The gifts could be something meaningful to your relationship or a hint that relates to the next destination
  • Be patient: Make sure the scavenger hunt is planned for a day and time when he’s available. Be mindful of his schedule so that he can fully enjoy the experience
  • Set the scene: At the final location, create a romantic ambiance with candles, fairy lights, or any other decor you think would be fitting
  • Ask him out: Ready with a terrible pickup line? When he arrives at the final location, be there with a big smile on your face. After enjoying the thrill of the scavenger hunt, give a confident head nod to your feelings and ask him out on a date
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2. Write a love letter

If you’re done trying asking a guy for his number, switch to the old fashion ways with a letter! Writing a love letter is a classic way to express your feelings and ask someone out. When writing your letter, be honest and open about your intentions. Tell the guy why you’re interested in him and what you admire about him. Include a clear invitation to go out on a date, and suggest a specific activity or location. Keep in mind that a love letter can be a vulnerable thing to share, so make sure you’re comfortable with your feelings before sending it.

3. Get a wingman (or woman)

Let’s tell you how to ask a guy out that you barely know. Asking a guy out for a drink isn’t a very difficult job if you do it right. A natural way to get a guy’s attention and show your interest in him is to ask a best friend to act as your ‘wing woman.’ This idea can also relieve some of your stress if you’re hesitant to approach him personally. Your companion can assist in establishing a comfortable and calm environment for both you and the guy. Notice his body language and see if he makes eye contact.

Let your friend talk and approach the guy in a casual and calm manner. She may start by introducing herself and then enquire about the guy. She can mention that you’ve been wanting to talk to him and that he should come and say “hi” if he seems interested and engaged in the conversation.

4. Make a cute video

Obsessing over “How do I ask him what his intentions are?” Or are you thinking about what to ask a guy you like? Asking the guy out in a creative way can be a fun and memorable way to make an impression. If you’re looking for some funny ways to ask a guy out, you could use quirky props to share a few laughs or a catchy song to make the video more interesting. Keep in mind that making a video can take some time and effort. So, make sure you’re comfortable with this great idea before diving in.

Related Reading: Why Would A Guy Reject You If He Likes You?

5. Ask him to join you for an activity

If you have a favorite activity, like hiking or playing basketball, or are attending a really cool sporting event, such as a beer fest or a concert, invite the guy to join you. Partaking in an activity together is a low pressure and stress-free way to spend some time together and get to know each other. This will also help you in knowing his intentions, thus solving your burning question: “How do I ask him what his intentions are?” Use that “extra ticket” excuse with him. 

6. Send him a care package

Now, this is often recommended as a cute way to ask a guy out. Putting together a care package is a sweet and thoughtful way to show a guy that you’re interested in him. Fill the package with his favorite snacks or small gifts, and include a cute note asking him out on a date. The package will show him that you’ve been paying attention to his likes and interests, and that you’re willing to put in effort to make him feel excited and special.

7. Plan a surprise date

Let’s help you in asking a man out on a date. Surprising a guy with a special first date is a great way to show him that you’re interested in getting to know him better. Think about his interests and then plan a local date invite that’s tailored to his preferences. It could be a night out at his favorite restaurant or a day trip to a nearby attraction. Make sure to keep the details a surprise until D-day, and watch his reaction when he realizes what you’ve planned. 

8. Cook for him

Cooking a guy’s favorite meal is a thoughtful gesture that shows you’re willing to put in effort to make him feel special. Invite him over for dinner, and make sure to ask about his dietary preferences or any allergies beforehand. You could even set a romantic table or light some candles to create a cozy atmosphere. Only a few people can pull this one off.

how to ask a man out
Inviting him over for a romantic, home-cooked meal speaks volumes of your feelings for him

9. Write a song or poem

If you’re wondering, “Should I ask him to hang out?”, well, you should! If you’re musically inclined, writing a song or a poem is a creative and unique way to ask a guy out. Use your talents to create something that expresses your feelings and ask him to go out with you. It’s a personal and intimate way to make a lasting impression.

10. Leave a message in a bottle

So, how to ask your crush for a date, you may ask! Writing your invitation on a piece of paper and putting it inside a bottle is a romantic and creative way to ask a guy out. Leave the bottle somewhere he’s likely to find it, such as on his doorstep or in his car. This is perfect if you don’t want to ask him out face-to-face. The unexpected surprise will make him smile and show him that you’re interested in getting to know him better. Here are a few examples for things to say to guys: 

  • “Roses are red, violets are blue, this message in a bottle is for you! Let’s have some laughs, good food, and a great time. Dinner with me on Friday? Circle Yes or No. ;)”
  • “Ahoy there, Captain [Crush’s Name]! I’ve got a special treasure hunt in mind, and it leads to a date with me! If you’re up for some fun and adventure, follow the clues to find the X that marks the spot. Hope to see you soon!”

Related Reading: 21 Qualities Of A Good Man To Look For To Get Married

11. Plan a picnic with him

Wondering how to hang out with a guy you like? One of the most unique ways to ask a guy out is in Mother Nature’s lap. Everybody loves nature, and a picnic is a classic and romantic way to spend some time together outdoors. Pack a basket with your favorite snacks and drinks, and invite the guy to join you for a relaxing afternoon in the park. You could even bring a blanket to sit on and enjoy the scenery with him.

12. Create a puzzle

There’s another fun and creative answer to the question, “How to ask a guy out on a date?” You can design a custom puzzle that reveals your invitation when it’s completed. You can also use a photo of the two of you or a favorite quote to make the puzzle personal and meaningful. Give the guy the puzzle and watch as he puts the pieces together and discovers your message.

13. Use a fortune cookie

There’s another answer to “How to ask your crush for a date?” Order a batch of fortune cookies and insert your invitation in one of them. Give the guy the cookies and wait for him to discover your message. It’s a playful and unexpected way to ask him out, and it’ll be a sweet surprise when he realizes what you’ve done.

Dating tips

Related Reading: 5 Ways To Deal With A Guy Who’s Not Ready To Commit

14. Ask him to help you with something

If you’re still wondering about how to ask a man out, then just ask him for help! If you need help with a task or project, ask the guy to lend a hand. While you’re working together, take the opportunity to ask him out. Tell him it’s a casual date. It’s such a natural way to spend time together, and it’ll give you a chance to get to know each other better. So, still wondering how to tell a guy you want to see him without sounding needy? Just ask for help using these examples:

  • DIY project: Ask him whether he’d be willing to assist you with your DIY project or any other home improvement project you’ve been putting off. Working together can result in a pleasurable and sociable experience, whether you’re painting a room, constructing a piece of furniture, or establishing a garden
  • Gardening: Ask him to assist you with planting flowers or veggies if you have a garden or intend to start one. Gardening is both joyful and soothing, especially when done with people you like
  • Tech help: Ask him whether he’d be ready to help you out with any tech-related activity, such as setting up a new device or fixing your computer

15. Organize a group outing

If you’re thinking about how to ask a guy out, especially one whom you barely know, then consider organizing a group date outing and inviting him to join. Plan a night out with your good friends, and encourage him to bring along some of his friends as well. This is a great way to spend some quality time together in a stress-free environment and to get to know each other better. Eventually, you can ask him out on a date.

16. Send a postcard

How to ask a guy out on a date, you may ask? Asking a man out on a date in person can sometimes be daunting. So, If you’re traveling or have been on any recent vacations, send the guy a postcard that asks him out. It’s a fun and unexpected way to make your intentions clear. If you’re worried about how to ask a man out, then you could even choose a postcard with a romantic or scenic image to make the gesture more special. Add a quirky pick-up line just for fun!

17. Start a conversation

Thinking how to ask your crush out over text? If you’re shy or nervous about asking a guy out, starting a conversation is a great way to break the ice and get comfortable with each other. Find common interests, share stories and experiences, and show a genuine interest in what he has to say. When you feel comfortable talking to him, take the opportunity to ask him out on a date. By building a connection first, you’ll know what to ask a guy you like and increase your chances of getting a positive response. Hopefully, you’ll not run out of things to discuss. Too difficult for your introverted soul? Take a look at these text message examples:

  • “What do you generally do on weekends for fun? I’m always trying to find new things to do.”
  • “Have you recently attended any cool performances or a really cool event? I want to go somewhere fun.”
  • What superpower, if any, would you choose to have and why?”
  • “Do you have a favorite food style? Being a foodie, I’m constantly searching for excellent restaurants.”
  • “What do you do to unwind after a stressful day?”

Related Reading: 6 Pro Tips To Find A Good Man For Once and All

18. Create a customized Spotify playlist

Make a Spotify playlist that includes songs that are meaningful to you and the guy. Include a note that asks him out and encourages him to listen to the playlist. Once you have a list of songs in mind, you can start building your playlist. Start by opening the Spotify app or website and clicking on the “New Playlist” button. Give your playlist a name that reflects the theme or sentiment you want to convey, such as ‘Love Songs for [Guy’s Name]’. What could be a better way to tell someone you love without saying it?

19. Trick him into asking you out

The key is to make it clear that you’re interested in spending time with him specifically. For example, you could say something like, “I’ve been dying to try out that new restaurant, but I haven’t found anyone who’s up for it. Too bad you’re not a foodie like me!” This lets him know that you’re interested in going with him, without being too obvious. There are similar ways to ask someone to a dance.

If he takes the bait and offers to take you to the restaurant or bowling alley, you can accept and suggest a specific day and time. Alternatively, if you’re wondering how to ask a guy out that you barely know, you could play it cool and say something like, “That sounds like fun, but I don’t want to put you out. Let me know if you’re ever up for it and maybe we can go together.”

20. Offer him an escape

Suppose you are in a group and you find him bored or disinterested, offer to take him to a better party or place you know he might love. Once outside, take him to a nice, quiet place and tell him you wanted to spend some time alone with him. This can be a park, a rooftop area, or a private seating area at a nearby coffee shop. Once you’re alone, have a one-on-one conversation and ask him out on a date. Without question, it’s one of the most thoughtful gestures to make someone fall in love with you.

how to ask your crush out
Take him out some place quiet and have a heart-to-heart

21. Play a fun game of questions

Ask him a series of questions as part of a game to know what he thinks about you. Before you ask him about the kind of girl he prefers, start by asking him some light-hearted questions. Ask him out on a date if you believe he is responding nicely.

As the game progresses, gradually move toward more personal topics. You could ask him about his ideal partner or what qualities he looks for in a girl. Pay attention to his answers. If he seems to be describing someone who sounds like you, this could be a sign that he’s interested in you. Here are some examples of questions you can ask him to get things going:

Related Reading: 13 Traits Of A High-Value Man | How To Attract A High-Quality Man

  • “What superpower, if any, would you choose to have and why?
  • “Where would you go if you could go anywhere in the world right now?
  • “Which animal, and why, would you like to be if you could be any other?
  • “Which age would you visit if you could travel through time, and why?”

Once you feel like you’ve built up a good rapport, take the opportunity to ask him out on a date. You could say something like, “I’ve had a lot of fun getting to know you better. Would you like to go out on a date with me sometime?”

Key Pointers

  • Asking a guy out can be nerve-wracking, but confidence is key. Believe in yourself and your worth, and remember that rejection is not a reflection of your value as a person. Find out new things to say to guys
  • Timing is important when it comes to asking someone out. Learn how to ask a guy out without sounding desperate
  • Wondering how to trick someone into asking you out over text? There are countless ways to ask a guy out. You can also look up how to ask your crush out over text
  • Whether it’s through a handwritten note, or a customized Spotify playlist, or ways to ask someone to a dance, a unique and thoughtful approach can leave a lasting impression. You’ll never run out of cute ways to ask a guy out over text
  • Learn how to ask a guy out without getting rejected. Remember, the guy may not feel the same way. So, use some reverse psychology if needed, and that’s okay

Approaching a guy for a date doesn’t have to be nerve wracking. Just make sure to know how to ask a guy out without sounding desperate. You can find a way to communicate your interest with one of the 21 original ideas mentioned in the article. Keep in mind that romantic rejection is a normal element of dating and does not determine your value.

Be positive, keep an open mind, and enjoy the experience. Who knows, your audacity and originality might just win the guy over and result in a wonderful date or a satisfying relationship. Lastly, at least try to find a guy who knows what to say other than “hey!” Take that initial step nevertheless because you never know where it might take you.

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