15 Ways to Start a Deep Conversation with Your Crush (Without Being Awkward)

Co-authored by Imad Jbara and Megaera Lorenz, PhD

Last Updated: February 10, 2023 References

Talking to your crush is the best way to get to know them better—and, hopefully, take your relationship to the next level. But sometimes, it can be hard to know what to say. In this article, we’ll share a few tips and tricks for starting a meaningful conversation with that special person.

1

Choose a moment when you both have time to chat.

Don’t try to talk when they’re busy or rushed. Instead, wait for a time when you’re both relaxed and won’t be interrupted. That way, you’ll have more time for a truly meaningful conversation.^{[1]
X
Research source}
- For instance, you might chat after school or work, or during a relaxed hangout session with mutual friends.

2

Ask them how they’re doing.

Build on their answer with follow-up questions. “How are you doing?” is a classic small-talk question. But it becomes a lot more meaningful if you ask it sincerely. No matter how they respond, ask a follow-up question to show that you’re really interested.^{[2]
X
Research source}
- For instance, if they say, “Pretty good, I’m glad to be back in school,” follow up with something like, “Me too! What’s your favorite class so far?”
- You could also try phrasing it another way to make it a little more specific or meaningful. For instance, say something like, “How’s work been going?” or “Have you started any new art projects lately?”

3

Comment on something they’re wearing.

Then, ask why it’s significant to them. Talking about someone’s clothes or accessories might sound kind of shallow, but it doesn’t have to be. Look for a way to use it as a starting point for a more interesting conversation.^{[3]
X
Expert Source

Imad Jbara
Dating Coach
Expert Interview. 12 February 2020.} For instance, say something like, “That’s a beautiful necklace. Does it have a special meaning for you?” or, “I love your St. Louis Zoo shirt. What’s your favorite animal there?”^{[4]
X
Research source}
- If they’re not wearing anything special, look for other items you can comment on, like a book they’re carrying.^{[5]
  X
  Research source}
- If you’re chatting online or over text, you could mention a picture you saw on their social media.

4

Bring up a shared interest or experience.

Talking about things you have in common can deepen your connection. It could be something like a movie you both like, a mutual friend, or a class you’re taking together. If you notice any connection, no matter how slight, bring it up!^{[6]
X
Research source}
- For instance, you might say something like, “I heard you saying to Natalie earlier that you’re into Lil Nas X. I love him! What’s your favorite of his songs?”
- If you have absolutely no clue what you have in common, talk about the experience you’re sharing right now. For example, “Wow, the décor in this coffee shop is wild. What do you think of that painting?”

5

Ask a thoughtful question.

Questions are a great way to take a convo to the next level.^{[7]
X
Expert Source

Imad Jbara
Dating Coach
Expert Interview. 12 February 2020.} But try to steer clear of questions that only require a “yes” or “no” answer. Instead, ask about things that will get you both thinking and help you get to know each other better. You could even turn it into a game where you take turns asking each other questions.^{[8]
X
Research source} For example, ask each other things like:^{[9]
X
Trustworthy Source
Greater Good in Action
An initiative by UC Berkeley's Greater Good Science Center promoting science-based practices for a meaningful life
Go to source}
- “If you could eat dinner with anyone in the world, alive or dead, who would it be?”
- “What would you consider a perfect day?”
- “What’s your favorite place in the world?”
- “If you could magically wake up with one new skill or ability, what would it be?”

6

Share something you wouldn’t normally open up about.

Don’t be afraid to get a bit vulnerable. You don’t have to share your deepest secrets (and you probably shouldn’t unless you already know your crush really well). But your conversation will feel deeper and more fulfilling if you’re willing to take a little risk! Get out of your comfort zone and say something that feels a little difficult or awkward to talk about.^{[10]
X
Research source}
- For instance, if they ask you how school is going, don’t just say, “Good.” Instead, you could say something like, “I’m excited to be back, but it’s actually a little overwhelming. I’m not used to being around so many people anymore.”
- Or, try sharing something you feel about them. You don’t have to confess your crush—just say something sincere, like, “You know, I really admire how creative you are,” or, “It’s so much fun spending time with you.”^{[11]
  X
  Expert Source
  
  Imad Jbara
  Dating Coach
  Expert Interview. 12 February 2020.}

7

Get them to teach you something.

If your crush is an expert in something, ask about it. For instance, maybe they’re a math whiz, they love to draw, or they know everything there is to know about crafting armor in Minecraft. Whatever it is, ask them to tell you about it—or, even better, ask them to show you how to do it.^{[12]
X
Research source}
- For example, say something like, “The way you draw hair blows my mind. How do you make the shading so realistic? Can you show me?”
- Not only will you have an interesting conversation, but your crush will probably be pretty flattered that you noticed their special skill!

8

Tell them an interesting story.

Or, ask them to tell you one. Talking about experiences you’ve had is a great way to get a meaningful conversation going. Try sharing news about something funny or exciting that happened to you recently, or bring up something unusual that happened to you in the past. You could even build the suspense by saying something like, “Something totally crazy happened to me yesterday. Meet me after class, and I’ll tell you all about it!”^{[13]
X
Research source}
- You might start by saying something like, “You’ll never guess who I ran into this morning,” or “Did I tell you about the time I accidentally dyed my hair green?”
- If you can’t think of anything to share, encourage them to tell a story. Say something like, “So, tell me about a time something really weird happened to you,” or, “I heard you adopted a new puppy! Tell me all about what it was like when you picked him out at the shelter.”

9

Talk about your goals and accomplishments.

Open up about what’s really important to you. Ask your crush about their hopes and dreams, too. For instance, you could talk about your dream jobs, where you each see yourselves in 5 years, and what you’ve done in life so far that you’re most proud of.^{[14]
X
Research source}
- Try starting the conversation by asking something like, “What would be your ideal job?” “What’s your biggest goal for after you graduate?” or, “What have you done in life that you’re the most proud of?”

10

Discuss your favorite books.

Reading a great book can be a truly meaningful experience. Sharing that experience with someone else makes it even more powerful! Ask your crush about the best book they’ve ever read, and tell them about some of your favorites. If they recommend a book you’ve never read, give it a try—then, tell your crush what you thought of it the next time you see them.^{[15]
X
Research source}
- You might even discover that you already share some favorite books or authors!

11

Start a conversation about art or music.

We’ve all been moved by powerful works of music or art. Bringing up these topics is a great way to open up a deeper conversation and really get to know each other. Ask your crush about their favorite piece of art or music, or talk to them about their favorite artist.
- For instance, you might ask something like, “What’s a song that never fails to make you cry?” or “What’s the first work of art you can remember seeing that really took your breath away?”
- If one or both of you is creative, talk about that. For example, you might ask to see a painting they’re working on, or tell them about a piece of music you’ve been practicing.

12

Speak sincerely.

Your crush is more likely to open up if you seem genuine. Don’t say anything insincere or untrue just because you’re trying to impress them or you think it’s what they want to hear. Just be yourself and be honest.^{[16]
X
Research source}
- For instance, don’t say you’re into their favorite hobby if you’re not. Instead, you might say something like, “I’ve never done that before, but it seems interesting. I’d like to learn more about it.”
- If they ask you a question, try to give them an honest answer. If you don’t want to answer at all, be honest about that, too. Say something like, “I don’t really feel comfortable talking about that.”
- Don’t be afraid to share opinions that conflict with theirs, but do it in a kind way. For instance, “I don’t really agree that the Beatles were the greatest band of all time, but I totally see why you feel that way. They were so innovative!”

13

Listen to what they have to say.

Listening is the key to any great conversation. When your crush is talking, give them your full attention. Don’t fiddle with your phone, interrupt, or plan what you’re going to say next. Instead, try to really hear and understand what they’re saying. You’ll get more out of the conversation that way, plus they’ll be more likely to want to keep talking to you!^{[17]
X
Research source}
- Let them know you’re listening by making eye contact and nodding.
- If you’re chatting over text, you can make brief comments to let them know you’re still there and paying attention, like, “Wow,” or “Seriously? OMG!”
- When they’re done talking, follow up with a question. For instance, say something like, “That sounds like an amazing trip. Do you have any plans to go back?”

14

Take it slow.

Don’t try to rush through the conversation. Take time to both listen and to think about how you want to respond. If they open up and say something meaningful or emotional, take a moment to process it—don’t just jump in with your own story. They’ll feel more comfortable having a deep discussion with you if they don’t feel pressured or worried that they’re boring you.^{[18]
X
Research source}
- For example, if they tell you about a tough situation that they’re dealing with, say something like, “Oh wow, that sounds like it must have been so difficult.” Then, stop and wait for a moment to see if they have anything else to say.
- If you feel tempted to fill every silent moment with chatter, force yourself to stop and take a breath. Take a minute to think about what you want to say next before you say it.

15

Don’t sweat the awkward moments.

They’re bound to happen, and they’re really no big deal. If something embarrassing happens during the conversation, take a few deep breaths and remind yourself that it’s not the end of the world. Awkward moments are a completely normal part of life, and they happen to everyone. You could even crack a joke about it—then quickly move on.^{[19]
X
Research source}
- For instance, if you forget something they said earlier, don’t beat yourself up. You could say something like, “Whoops—that’s me, Captain Amnesia!” Then, go on with the conversation.
- If you say something that offends them, don’t make a big deal out of it. Just say, “Sorry, that was a little insensitive. It won’t happen again.”