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How to Start a Conversation with Your Crush – 48 Foolproof Ways

Are you dying to talk to your crush, but don’t know where to begin? No worries – we are here to help you break down exactly how to start a conversation with your crush. Let’s check out 48 great approaches you can choose from today.

Table of Contents

Most important things to remember

Speaking to someone you like doesn’t have to be nerve-wracking. You have had hundreds of conversations in the past, so think of it as if you’ve been training for this your whole life!

Remember to smile and be genuine. The goal is to get to know your crush better and vice versa, so you should truly be yourself. This means sharing a little bit about yourself, even if that means showing your quirks.

Remember that no interaction is perfect. While you might obsess over speaking to your crush this time, it probably won’t be the last time you two share a nice conversation. Keeping this in mind could relieve a bit of the pressure you feel at the moment.

Finally, remember that your crush is simply another human being. While you may put them on a pedestal in your mind, they also experience awkward moments and self-doubt. To be frank, they may be just as nervous to chat as you are! Keep it light and have fun.

Preparing before the conversation

Even if you’re a confident person, it’s vital to prepare before important conversations – including speaking to your crush.

First, you should choose a couple of great conversation starters from the list below and commit them to memory. If you have the chance, practice them first with a friend or family member. This will help you play around with potential scenarios and changes in conversation.

When choosing the time and place to speak to your crush, think about what will be going on around you. You don’t want any big distractions or loud noises to make talking more difficult, so avoid noisy or overcrowded areas.

You should also choose a time when you know your crush will have at least a few minutes to speak without interruption, such as at the beginning of a shared lunch break or a casual event with a lot of downtime.

Finally, put some effort into your appearance before meeting with your crush. First impressions count, so don’t forget to brush your teeth and pop a mint to keep your breath fresh.

Starting and having the conversation

Courage is the most important thing you need to start and have a conversation with your crush. It’s ok if you aren’t the most confident person in the room – that will rarely be the case for most of us – but you do need to take a breath, take a step, and get started.

To smother your nerves, think about your crush as if they’re a friend or acquaintance you already know. The less you wait and think about it the better.

The most difficult part of this is knowing what to say and, luckily, we’ve got you covered with 48 options below. Unfortunately, I can’t start the conversation for you since you’ll be the one approaching your crush, but we’re all rooting for you and know it will turn out great!

After the conversation

You may want to immediately reach out to your crush after talking with them, but it’s best to wait a bit before doing so. If you’re reading this article, it means that you and your crush don’t speak often. You don’t want to go from zero to 100 by immediately contacting them again after you two chat, as this could be overwhelming for them.

Instead, give your crush a day or two to reflect on your conversation. This will allow them to think more about you, and it may even inspire them to wonder when they’ll see you again.

After you wait a full day or two, feel free to send them a short and sweet message or meme to say hello. A good option for this is to say you saw something that reminded you of your previous conversation. Ideally, they will respond positively and you can start your second conversation together.

48 Ways to start a conversation with your crush

1. Introduce yourself

Sometimes, it’s best to start with the basics. There’s no need to overthink this one – simply walk up to your crush and introduce yourself. This works best when they’re standing alone nearby, especially if you’re both at a social event or somewhere like work or school.

Your crush will introduce themselves back out of common courtesy and, afterward, you can choose another great conversation starter from this list to keep the chat going.

2. Ask them to settle a bet

To use this starter, you’ll need to be with a group of people or have a conversation with a friend on your phone. Technically, you could even pretend you were texting someone just to initiate this conversation.

Tell your crush that you and your friend can’t come to terms with something and that he needs to be the tiebreaker. For example, “What’s better, burgers or tacos? The Yankees or the Red Sox? Camping or 5-star hotels?”

Remember that this bet could be completely imaginary, so the key is to pick something general enough to get the conversation started.

3. Reference one of their interests

A great conversation starter is anything your crush is interested in. If you always hear them talking about a certain musician, for example, you could ask if they’ve heard their latest album.

If you don’t know much about your crush, try to learn through observation. A great trick for this is through style. Do they wear t-shirts from certain brands, events, or sports teams? Do they have any stickers or magnets on their car? Use these clues to start a casual conversation and learn more about them.

4. Share a funny video

You could send your crush a funny video or show it to them in person. If it’s in-person, make sure you watch the video first and laugh audibly. Then, pass it along to them to share the humor.

If you send them the video through text or social media, pair it with a few laughing emojis and hope they have the same sense of humor as you do.

5. Stick to the trends

Some of the easiest conversation starters are whatever is trending that week. You can figure these out by doing a quick scroll through your social media, reading the most popular news articles, or even by Googling “trending topics today.”

Ask your crush if they’ve seen this trend, participated in it, or if they like it at all.

6. Use a holiday as an excuse

How many times have we seen an ex or an interested suitor message us on a holiday? These are optimal times to reach out to someone you barely speak to because they are nationally-recognized days that everyone shares.

Pick and choose your holidays carefully. It wouldn’t make much sense to wish your crush a happy President’s Day, but you would be safe with Christmas, Valentine’s Day, Fourth of July, or any other big ones.

7. Don’t overthink

Sometimes our natural ability to spark great conversation beats any planning. If you have been introduced to your crush before, why not walk up to them and talk about whatever comes to mind?

After an initial greeting and asking how they’ve been, you can discuss where you are, what you have both been doing, or any other topic that comes up. Trust your gut on this one.

8. Use your pet as an icebreaker

Who doesn’t love a good photo of a pet or a cute pet story? If your crush doesn’t, they might not deserve to be your crush in the first place.

If you have a dog, try to take it for a walk around a place your crush frequents. If your pet isn’t walkable, show a photo or video of them to your crush and watch their reaction. They’re likely to ask you more about your pet or share which pets they love themselves.

9. Let them take the lead

If you start with a “hey” and a smile, your crush might just take the pressure off of your hands. This works especially well if your crush is a known extrovert or tends to be popular in social settings. This means they know how to lead a room – and a conversation – so they’re likely to push your chat forward on their own.

10. Ask for their recommendation

The best part about asking your crush for a recommendation is that they will both feel appreciated and you’ll get to learn more about what they like.

Try asking them for recommendations for things to do in town, the best places to eat, their favorite tv series to watch, or anything else you can think of. If you or your crush are confident enough, you can even ask each other to see or do the recommended activity together!

11. Ask what they’re listening to

If your crush has headphones on, they may want to be left alone. If they have only one headphone in, this could signal their openness to speak with someone.

You can also ask what they’re listening to if they’re watching a video on their phone. Ideally, you’ll already be close enough to hear the video so that it doesn’t seem like you appeared out of thin air.

12. Go to them with exciting news

Whether your home team just won the championship game, you received the promotion you’ve been waiting for, or you just heard the best news in the world, share it with your crush. Most of the time joy is contagious, which means your crush will get excited with you as you two share a beautiful celebratory moment.

13. Talk about or show them a weird thing

If something strange happened to you that day or you noticed something odd, you can bring it to your crush’s attention. They’ll be able to comment on it and you could share a “shaking-my-head” moment where you’re both in disbelief about how weird something or someone is.

14. Respond to their social media stories

This is probably one of the most-used conversation starters and for good reason – it’s just so easy. Chances are your crush will eventually post a story on Instagram, Snapchat, or another social media platform. Take the opportunity to reply to their story and see if you can start a conversation.

Don’t just send them a fire emoji or heart-eyes. Avoid hitting on them altogether in these responses. Instead, take the time to respond to something or someplace that they post, writing about how cool it is or asking for more details about what’s happening.

15. Use your environment

Your environment is full of clues for new conversation starters. Most of these are small-talk conversation topics, but that’s just what you need to get the conversation started.

If you’re both in the same place, you can ask how they ended up there or how long they’ve been there. If it starts raining, you can comment on the weather or ask them about the forecast.

16. Join their friend group

If your crush is with a group of people and you know someone in that group, take the opportunity to approach that person first. After saying hello or chatting with them for a minute or two, introduce yourself to the rest of the group. You’ll then be able to slowly make your way to your crush and speak to them one-on-one.

17. Be curious

It’s normal to want to learn more about your crush. Use this natural curiosity to lead the way in your conversation. Whether you want to learn about what hobbies they like, where they’re from, or what they’re studying, let these natural questions lead the way.

18. Play “would you rather”

“Would you rather” could be a serious game to get to know someone or it could be a riot if you choose to ask funny questions. Depending on your comfort level, why not propose this game when you’re both bored? This could be done in person or on the phone.

19. Ask for advice

Us humans love to give advice, even if most of the time it’s unsolicited! If you ask your crush for advice, they’re sure to jump at the chance to either help or show off their knowledge.

You can ask for advice about anything from a small choice you have to make to a big problem you have at home. The more genuine you are, the more likely your crush will be able to provide guidance and feel connected to you.

20. Challenge them

A big part of flirting is starting a competition. Challenge your crush either realistically or hypothetically. For example, if you hear your crush talk about a meal they made, you could say there’s no way your crush is a better cook than you are. Or, if they’re athletic, you could mention that you’d beat them at their sport any day.

All of these challenges should be done in a light-hearted way and with a smile. If your crush accepts your challenge, you have opened the door to set up a challenge/date in the future!

21. Send them a meme or GIF

Everyone likes a good meme or GIF now and again (or daily). If you see a meme that you think your crush would enjoy, send it to them through a text or direct message (DM).

GIFs are best saved for conversations through text, but you can also begin a conversation by sending them a GIF related to the last time you saw them or to something you both saw that day.

22. Ask open-ended questions

Questions like “How are you?” and “Where are you from?” will only take your conversation so far. Instead, focus on open-ended questions that must be answered with more than one word.

A few examples include, “What do you like to do in your free time?” or “Where would like to go on vacation and why?”

23. Tell them a joke

Humor provokes positive feelings which create a sense of connection with one another. After all, wouldn’t most people prefer a partner who can lift their spirits if they’re feeling down?

Now is the time to break out your best joke. You can open up by asking your crush if they want to hear something funny, then lay the joke on them. Of course, try to keep it PG and non-offensive – especially if you don’t know your crush very well yet.

24. Invite them out, casually

You don’t always need to have a ton of conversation before hanging out with someone. That’s why you might be able to invite your crush out casually right at the start of your conversation.

This works great if you’re already in a group setting. You could propose some casual plans to the group, and then tell your crush they should join in. This creates an inviting tone without the pressure of a one-on-one date.

25. Ask hypothetical questions

If you’d rather skip the small talk and already know the basics about your crush, you can fill the silence with some fun or funny questions. These can be as real-life or absurd as you want, which makes them even more fun.

For example, you could ask something low-key like, “Where would you rather live, South America or Asia?” or something silly like, “Would you rather have three eyes or twenty fingers?” No matter which you choose, your crush is sure to be intrigued!

26. Have some backup stories

Conversation lulls are often unavoidable. Eventually, there will be a pause in conversation – even if that person is your soulmate. If silence makes you uncomfortable, it’s helpful to have some interesting backup stories in your arsenal.

Think of a couple of really cool, strange, or interesting things that you’ve experienced in the past. If you’re with your crush and draw a blank, say, “You know what happened to me a while ago?” and lead into one of your backup stories.

27. Find out what they like

Most of the time, the majority of information we know about our crushes is gathered through watching them from afar. While social-media stalking can give you some intel, you can find out more about your crush by simply asking them what they’re into.

By having an interest in their hobbies, interests, likes, and dislikes, you show this person that you want to get to know the real them. Plus, these conversation topics are easy to talk about, so your crush should be enthusiastically chatting with you in no time.

28. Approach them within 5 seconds

If you or your crush enter a room and notice each other, it’s time to act. Impart the 5 Second Decision Rule. This is when you know you should do something – like talk to your crush – so you start doing it within 5 seconds or less. You should immediately start the countdown in your mind to get you going.

Why five seconds? Any longer and you’ll talk yourself out of it.

29. Wait for a celebration

Celebratory events always call for a “congratulations.” These are easy excuses to start speaking to your crush. First, you congratulate them. Second, you ask them about whatever they’re celebrating. Suddenly, you’re both chipper and exchanging pleasantries.

Some celebratory events to look out for include birthdays, graduations, promotions, and when a new relative (e.g., niece, nephew, sibling) is born.

30. Give them a compliment

Starting a conversation with a compliment instantaneously sets a flirty tone for the conversation. This is a way to make your crush feel good about themselves while saying you notice them in a potentially-romantic way.

If this sounds too intense for you, keep it simple and tell them that they look nice today.

31. Ask about their relationship status

You like your crush and ideally want to date them, right? Why not get straight to the point? Say hi and ask them if they’re there with their boyfriend or girlfriend. If they say they aren’t, you can ask why. In less than two minutes you’ll know if they’re available or taken.

32. Smile and stare (but only for 3 seconds!)

One scientific study investigated the connection between eye contact and arousal. The study showed that people preferred glances from potential partners that were 3 seconds. Shorter stares didn’t stick in their memories and longer stares were uncomfortable.

If your crush potentially likes you back, smile and stare at them for three seconds, then look away. They might come over to start talking to you themselves!

33. Focus on things you have in common

A conversation truly flows when both people involved are enjoying the topic. Avoid talking about obscure topics or only about yourself. You have a greater chance of creating enjoyable dialogue if you talk about hobbies or interests that you both share.

34. Ask them to help you out

Most kind people will offer to help if needed. Since I hope your crush is a nice person, why not start a conversation by asking them to help you out or for a favor?

Choose something simple to get started, like asking for directions. You don’t want to ask them to help you with something big on day one or they may avoid you moving forward.

35. Slide into their DMs

“Sliding into a DM” is direct-messaging someone on social media, usually to hit on them.

While many DMs are too much or grimace-worthy, you can still use a DM to send a subtle message. A simple “Hey, what’s up?” will do and it spares you the nerves of speaking up in person… for now, that is.

36. Give them a dare

Much like the challenge in #20, proposing a little dare is a sure way to grab your crush’s attention. You can use whatever you have around you for inspiration. If they have a drink in hand, dare them to finish it in one try. If you’re both in a boring group setting, dare them to sneak out with you. Your dares can be as creative as you are – without being too risky, of course.

37. Ask if they know about one of your interests

You may not know what your crush is into, but you definitely know what you like. You can play a snippet from your favorite musician or a video from your favorite influencer on your phone, then turn to your crush and ask them if they know the person.

This also works if you’re talking to a friend and your crush is within earshot. It’s a great way to sneakily add them into the conversation.

38. Propose a random bet

If you’re surrounded by people or activities, a great way to approach your crush is by proposing a random bet. You could bet that something specific happens in the next 5 minutes or that someone will say a specific phrase.

These bets are used to lighten the mood, so even if you say “I bet you $100 that…” most crushes will join in and know it’s just said in good fun.

39. Show them you care

While humor and compliments are great, kindness and connection are also found in sad or serious situations. If your crush is going through something somber, show them that you care by giving your condolences or telling them you’re there for them if they need anything.

40. Play 21 questions

This conversation starter works best for phone calls, texting, or chatting online. If you already know your crush and have spoken before, you can spice up a new conversation by asking them to play 21 questions.

Twenty-one questions is a simple game where one person asks another a series of 21 questions to get to know them better. Your crush will have to answer truthfully. You can even ask them who they’re into!

41. Talk about an upcoming event

If you and your crush both live in the same city, there are likely some upcoming events you can discuss. Conferences, sports games, concerts, fairs, and other things happen in or near most towns year-round.

Choose one and ask your crush if they plan to go or if they know anything about it. Another tip is to be sure you know something about it before you bring it up.

42. Ask about their family

If there’s one thing you know about your crush, it’s that they were raised by some human out there. Take the opportunity and ask them about their family to spark conversation. You can start vaguely, by asking if their family is from the area, and then get into the details by asking about siblings and family experiences.

43. Discuss pet peeves

This is a good starter if and only if you’ve spoken to your crush at least twice before. You don’t want to meet your crush and discuss peeves right off the bat because you may come off as a negative person. If they’ve already had a chance to see you speaking about more neutral or happier topics, give this one a go.

Start by pointing out something you can’t stand in your surroundings. Then, ask him about his own pet peeves.

44. Act as If You Know Them

This approach is a bit of a fib, but an innocent one with a good cause. For this to work, you can’t have met your crush before.

Go up to them and act as if you know them. You can say, “Aren’t you so-and-so?” or “You’re so-and-so’s friend, right?” Of course, they will say no, after which you can laugh, apologize, and then introduce yourself.

45. Help them if they need it

If your crush drops their belongings, trips, falls, seems lost, or hurts themselves, this is your time to shine. Approach them and offer your help however possible. You’ll always be remembered as the kind guy or gal of the moment.

46. Talk about their past experiences

A good conversation starter with your crush is to ask them about something you know they experienced.

If they moved to your city recently, you can ask them how that transition went. If they used to work at a different company, ask them about their time there. So long as they lived it, they will have something to share.

47. Show enthusiasm

No matter which question or approach you choose, it’s essential to show enthusiasm. Speak to your crush with a smile, open body language, strong eye contact, and an inviting tone. If they change the topic, welcome it with enthusiasm and go with the flow. The delivery of your words matters more than the actual conversation.

48. Follow up on an old topic

If you’ve spoken to your crush before, even in a group setting, it’s time to use your recall to your advantage. Think about something your crush mentioned in that previous conversation. This could be an upcoming event, a challenge they were facing, their opinion about something, or anything of the sort.

When you see them next, follow up about that topic. They’ll be impressed that you remembered and will be able to update you on what’s happened since.

FAQs about starting a conversation with your crush

Is text or in-person better?

Nowadays, most initial conversations with a crush begin over text or through social media. If you know you’ll run into your crush, though, approaching them in person is always admirable and more memorable.

While texting is less nerve-wracking compared to in-person encounters, it will only take you so far. Eventually, you’ll have to meet your crush in person, so don’t delay it for too long.

I’m too nervous, what do I do?

Feeling nervous around your crush is perfectly normal! You can get over these nerves by hanging out with your crush in a group setting with other friends. Then, start talking to them one-on-one via text or social media. You’ll soon have the confidence to approach them privately.

What if they don’t seem interested?

Your crush might not seem interested because they’re overwhelmed personally, don’t want to date anyone, or a million other reasons. The best you can do is try.

If they aren’t reciprocating your effort, it’s time to focus on you and keep moving forward. While it sounds cliché, there truly are another 3-4 billion fish in the sea, and you deserve one that wants to swim alongside you!

How long should I wait before talking to them again?

While I’m not a fan of hard rules when it comes to initiating contact, it’s true that you shouldn’t come on too strong. I would suggest waiting at least 1-2 days to give your crush some room to breathe and reflect before your next conversation.

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