How to Start a Conversation with Your Crush Without It Being Awkward

If you want to strike up a conversation with a special someone but you’re not sure where to start, look no further! We’ve compiled a complete guide on how to talk to your crush without any awkwardness, including expert advice from matchmakers and dating coaches. Keep reading to learn how to impress them with your dazzling conversation skills, and hopefully leave them wanting to hang out with you more!

How to Start a Convo with Your Crush

Choose a low-stress, distraction-free time to start the conversation.
Say “hello” and introduce yourself if you haven’t spoken to them before.
Make funny or playful comments about your surroundings.
Ask them questions about their hobbies, interests, and life.
Ask follow-up questions to deepen the conversation.
Once the convo is flowing, ask if they want to hang out or ask for their number.
End the conversation on a good note and say you enjoyed talking to them.

Sample Conversation Topics

Sample Ways to Talk to Your Crush

Sample Conversation Topics to Avoid

Section 1 of 4:

Starting the Conversation

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1
Make a funny or playful comment about your surroundings. Dating and relationship coach Julianne Cantarella suggests using humor as an icebreaker, since so many people find humor attractive.^{[1]
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Expert Source

Julianne Cantarella
Dating & Relationship Coach

Expert Interview. 6 August 2021.} Look around and observe what is going on around you. Is there anything funny or interesting that you notice? For example, if it’s lunchtime and the food truck hasn’t arrived yet, you can say “Are they going to get us water for this wait, or do they want us to die?” A humorous or playful comment like this can help keep the mood light and fun.
- If you’re starting your conversation over text, you won’t be able to comment on your physical surroundings, but you can still make a comment about something that happened during the day.
- For example, if you’re in the same English class, you could say, “I feel like that quiz in English was super hard! I practically died 😵‍💫 What did you think?”
- Try not to overthink your icebreaker and don’t worry too much about being “smooth.” The first few comments you make to your crush are not going to make or break the conversation. The important thing is to get the two of you talking.
2
Ask an icebreaker question to get things going. If there's nothing interesting in your surroundings to comment on, try asking them a casual question about how they’re doing or what they’re up to. For example, “I see you have some books with you, what are you reading?” Or, if you’re having a conversation over text, start with something like, “Hey, how’s your day going?” These low-pressure questions let your crush know you’re interested in them in a cool and casual way.
- After they answer your first question, ask some follow-ups to deepen the conversation. For example, once they tell you what book they’re reading, ask them whether it’s any good, or how it compares to other books by that author.
- If you go to the same school and you see them at lunch, you could say something like, "Have anything good to eat today?" or "How was class this morning?"
- If you’re coworkers, casual questions like, “How’d your day go?” or “What projects have you been working on lately?” work well too.
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3
Ask for an update about something going on in their life. It's an especially good idea to ask about a topic the two of you have in common, explains matchmaker and dating coach Judith Gottesman.^{[2]
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Expert Source

Judith Gottesman, MSW
Matchmaker & Dating Coach

Expert Interview. 19 October 2021.} For example, if you’re taking a class together, you could say “So how’s your midterm paper coming together?” Talking about the things you have in common will make the conversation less awkward, and you’ll also get a better understanding of what’s going on with them.
- Although it is a good idea to share information about yourself throughout the conversation, Gottesman warns not to talk about yourself too much. “I would advise asking them questions about themselves and talking less about yourself,” she says.^{[3]
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  Expert Source
  
  Judith Gottesman, MSW
  Matchmaker & Dating Coach
  
  Expert Interview. 19 October 2021.}
- Tell them about what’s going on in your life when they ask or when it comes up naturally, but aside from that, try to keep your focus on them.
- If you’re going on and on about yourself, they might feel like you’re trying too hard to impress them. “It’s almost like you’re reading a resume off to them, and you don’t want to do that,” Gottesman says.^{[4]
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  Expert Source
  
  Judith Gottesman, MSW
  Matchmaker & Dating Coach
  
  Expert Interview. 19 October 2021.}
4
Ask for their opinion on something. You can ask them something general, like "What's your favorite song right now," or you can ask them something related to your surroundings. For example, if you’re eating an apple at lunch, you could say, “I personally know that Granny Smith apples are the best apples in the world, but out of curiosity, what kind is your favorite?” ^{[5]
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Research source} Once again, being playful is a good way to make your conversation less awkward and more fun.
- Just remember, you don’t want to ask them something too controversial. Stay away from any hot button topics like politics or religion.^{[6]
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  American Psychological Association
  Leading scientific and professional organization of licensed psychologists
  
  Go to source}
5
Ask them something unexpected but easy to answer. Dating coach Imad Jbara recommends asking your crush something illogical and fun.^{[7]
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Expert Source

Imad Jbara
Dating Coach

Expert Interview. 22 September 2021.} An unusual or unexpected question can really help you stand out and make the conversation more interesting and memorable. For example, you could ask them something like, “Is there a celebrity that people say you look like?”
- This kind of question could make them laugh, and the playful topic can help you feel more comfortable with one another.
- Once they tell you their celebrity look alike, you can tell them who you think yours is. You can even joke around and pick someone who doesn’t look like you to make them laugh more.

Section 2 of 4:

Keeping the Conversation Going

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1
Bring the conversation back to something you already talked about. Mention something your crush talked about at the beginning of the conversation to bring the things full-circle. For example, you could say, “So how much longer do you think you need to spend on your midterm paper?” This will show that you were really paying attention and locking in the information they shared with you.
- You can also make inside jokes about what you talked about. For example, you can say, “Well now that we have made it through this lunch period without water, I suppose we can get through anything together.”
- Making inside jokes can help you cement connections you have made, and it's a good way to make your connection last past the first conversation.
2
Make a plan to hang out again and/or ask them for their number. If the conversation seems to be going well, ask your crush if they want to hang out sometime, or ask for their number so you can keep talking over text. Try to do this after you’ve been talking for a period of time, but not at the very end of the conversation. You want to do it after you’re made a solid connection, but before the conversation has become tired or worn out.
- For example, you could say something like, “I think you’re super cool. Would you want to hang out sometime?” Then suggest a couple of things you can do together, and ask for their number so you can coordinate the plans.
- Or if you want to play it safer, you can simply ask “Hey, can I have your number? I really like talking to you and it would be cool if we could keep the convo going.”
- This part can be a little nerve-wracking, but it’s important to put yourself out there. “There are too many good relationships that people miss out on because they’re too afraid to show interest, or they think they should play it cool,” says Gottesman.^{[8]
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  Expert Source
  
  Judith Gottesman, MSW
  Matchmaker & Dating Coach
  
  Expert Interview. 19 October 2021.} So don’t be afraid to shoot your shot!
3
End the conversation on a good note. When you’re feeling good and you’ve just finished laughing about something, it may be a good time to politely end your conversation. This leaves your crush with a good impression and ends the conversation on a high note. Make sure to tell them that you enjoyed talking to them, and that you’re looking forward to chatting again soon.
- You can keep the end of your conversation casual with something like, “I should be getting home now, but I had a lot of fun talking to you. Let me know how that game goes on Friday!”
- If you are going to be seeing your crush in the future, try saying something like, “I’ll see you in math class tomorrow! I’m also around later if you have any trouble with the homework—just shoot me a text.”
- If they gave you their number, send a follow-up text in the next couple of days to say hello and check in with them about the things you talked about.

Section 3 of 4:

Tips for Having a Great Convo with Your Crush

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1
Wait for the right time and place to start a conversation. A lot of awkwardness can be avoided if you find a good time to talk to your crush. A good time to start a conversation could be before school, during lunch or a break, after school, or after an event is over. Just make sure they aren’t stressed out or in the middle of something—you don’t want to interrupt them when they’re busy!
- Make sure you have enough time for at least a few minutes of conversation. For example, you don’t want to try to talk to them right before class starts, since your conversation will likely get cut short.
- Try to find times when your schedules overlap. If you have two classes in a row together, for instance, you start a conversation while you walk from one class to the next.
- Think about whether there are any dances, parties, or school events coming up that you’re both going to. These are great settings for you to talk to them!
- This is less of an issue if you’re starting your conversation over text, since they can reply to your message whenever it’s convenient for them. Just try not to text them super late at night or really early in the morning. You don’t want to wake them up if they’re sleeping!
2
Freshen your breath before you talk. This is an easy way to feel confident in yourself and avoid awkwardness. Buy a pack of sugarless gum to take with you to school or wherever you meet your crush. Pop a piece in your mouth 5 minutes after a meal or a few minutes before you talk with your crush to make sure you have fresh breath when you chat with them.^{[9]
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Cleveland Clinic
Educational website from one of the world's leading hospitals

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- If you’re going to a dance or somewhere you might be up close and personal with them, you can gargle with mouthwash after you brush your teeth to freshen your breath, as well.
- Avoid eating foods that are known to affect your breath (like onions and garlic) right before talking to your crush.
- Drink a glass of water after eating. This will flush out some of the food and bacteria that can cause bad breath.^{[10]
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3
Talk to your crush like you already know them. Conversations can be awkward if one person is extra stiff with the other person or treats them like a stranger. Instead, try to use a warm, friendly tone when you talk to your crush, even if you don’t know them all that well yet. This creates a comfortable vibe and helps smooth over any awkwardness. ^{[11]
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Research source} Say something like, “Hi, I don’t know if we’ve actually met yet, but we’re in the same math class. I’m Tim, how’s it going?”
- When you’re talking to your friends, pay attention to your tone of voice, the hand gestures you use, and the expressions you make. Try to use these same relaxed and natural mannerisms when you talk with your crush.
- Try to keep the vibe cool and low-key, and don’t overthink it. If you’ve already been introduced to each other, a simple, “Hey, how are you?” or “What’s up?” can be enough to start a casual conversation.
- Just make sure not to be overly familiar with them, either. For example, if you’ve never spoken to each other before, you wouldn’t want to say something super casual, like “Hey dude. How’s it?” You’d want to introduce yourself first.
EXPERT TIP

John Keegan
Dating Coach
John Keegan is a Dating Coach and motivational speaker based in New York City. With over 10 years of professional experience, he runs The Awakened Lifestyle, where he uses his expertise in dating, attraction, and social dynamics to help people find love. He teaches and holds dating workshops internationally, from Los Angeles to London and from Rio de Janeiro to Prague. His work has been featured in the New York Times, Humans of New York, and Men's Health.

John Keegan
Dating Coach

Chatting doesn't have to be stressful! A playful and lighthearted approach makes conversations fun and enjoyable. Be genuinely curious about the conversation—don't hesitate to share engaging things about yourself!
4
Be an active listener in your conversation. Your crush will enjoy their conversation with you much more if you’re a good listener. This shows that you’re fully engaged and interested in what they’re saying, which helps you feel more connected to each other.^{[12]
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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} Here are some important active listening tips to follow during your conversation:
- Use engaged body language. “That means eye contact, that means facing your legs and feet towards the person you’re speaking to,” explains matchmaker Erika Kaplan.^{[13]
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  Expert Source
  
  Erika Kaplan
  Dating Coach
  
  Expert Interview. 1 October 2020.} These may seem like small things, but Kaplan says good body language can be the thing that keeps you out of the friendzone!
- Avoid distractions. Don’t send a text or look at your phone while you talk. This will make it seem like you are disinterested, and it might keep you from really hearing what your crush is saying.
- Repeat what your crush said and ask follow-up questions. Rephrasing what they said lets them know you’re paying attention, and asking a follow-up keeps the conversation flowing. For example, “Wow, it’s so crazy you ran into your best friend from kindergarten! Was it nice to catch up?”^{[14]
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  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}
- Avoid interrupting them. It’s normal to get excited about what you want to say, but resist the temptation to interrupt while they’re still talking. Wait until they’re done before making a comment or asking another question.
- Be empathetic. If your crush talks about something hard that is going on with them, make sure to acknowledge their feelings. For example, if they talk about failing a test, you could say something like, “That sounds like a super tough test! I’m sorry it didn’t go well. Are they letting you retake it?”
5
Show them you’re enjoying yourself. One way to keep a conversation friendly and natural is to make it clear that you’re having a good time. A few ways to show this include making eye contact, smiling often, laughing at their jokes, and leaning forward slightly when you are talking.^{[15]
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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}
- Tilting your head to one side is another good way to show friendliness or playfulness when you’re flirting.

Section 4 of 4:

Conversation Ideas & Questions to Ask Your Crush

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Brainstorm convo topics based on what they’re interested in. If you’re familiar with your crush's interests, life, friends, likes, dislikes, use these things as jumping-off points to get your conversation started. For example, “Maybe they’re a scuba diver and you’ve never been scuba diving, but you find it very interesting. You can talk to them about that,” suggests Cantarella.^{[16]
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Expert Source

Julianne Cantarella
Dating & Relationship Coach

Expert Interview. 6 August 2021.}
- Make sure to bring up their interests in a way that is natural and casual. You don’t want to act like you know everything about their life if you haven’t hung out that much yet.
- Stick to talking about things that are public knowledge, like the fact that they are on the football team, or that they’re in the school musical that’s coming up.
- For example, you could say something like, “Are you excited for the game on Friday?” or “How are rehearsals going? I’m excited to see the show.”
2
Ask them interesting questions to have a meaningful conversation. According to Jbara, this is a great way to form a real connection and grow closer to them. “I’m telling you, it works like magic, and the reason why is that it starts developing a level of intimacy…in learning more about them, you feel deeper and closer,” he says.^{[17]
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Expert Source

Imad Jbara
Dating Coach

Expert Interview. 22 September 2021.} If you have trouble coming up with good questions on the spot, here are a few you can use the next time you're talking to your crush:
- What do you think is the best movie ever made?
- Have you discovered any cool new artists or songs lately?
- Do you have any good TV show recommendations?
- Are you more of a morning person, or are you a night owl?
- Do you like home cooked food or takeout better?
- What do you like to do on the weekends?
- What’s the funniest joke you’ve ever heard?
- What was your most embarrassing moment?
- Who is your favorite fictional character?
- If you could meet any celebrity, who would you choose?
- What’s your most prized possession?
- What’s the funnest thing you’ve ever done?
- What’s your favorite childhood memory?
- What’s a fun fact about you that would surprise people?
- How do you recharge when you’re stressed?

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Question

How do you respond when your crush compliments you?

Erika Kaplan
Relationship Advisor
Erika Kaplan is a Dating Coach and Matchmaker for Three Day Rule, an exclusive matchmaking company across nine cities in the United States. With over six years of experience, Erika specializes in helping singles find quality matches through date coaching and premium matchmaking services. Erika graduated from Penn State with a Bachelor’s degree in Public Relations. She worked for Rolling Stone, Us Weekly, and Men’s Journal before leaving publishing to pursue her passion for connecting people. Erika has been featured on Lifetime, the Philadelphia Inquirer, and CBS as well as in Thrillist, Elite Daily, Men’s Health, Fast Company, and Refinery29.

Erika Kaplan

Relationship Advisor

Expert Answer

Try to embrace the idea of being grateful for a compliment! Men and women are constantly looking for someone who is self-assured and comfortable in their own skin, and if you show awkwardness when getting a compliment from your crush, you may end up giving the wrong message.

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Question

Why is it hard to accept compliments?

Erika Kaplan
Relationship Advisor
Erika Kaplan is a Dating Coach and Matchmaker for Three Day Rule, an exclusive matchmaking company across nine cities in the United States. With over six years of experience, Erika specializes in helping singles find quality matches through date coaching and premium matchmaking services. Erika graduated from Penn State with a Bachelor’s degree in Public Relations. She worked for Rolling Stone, Us Weekly, and Men’s Journal before leaving publishing to pursue her passion for connecting people. Erika has been featured on Lifetime, the Philadelphia Inquirer, and CBS as well as in Thrillist, Elite Daily, Men’s Health, Fast Company, and Refinery29.

Erika Kaplan

Relationship Advisor

Expert Answer

If you have difficulty in being grateful for someone's compliment, it probably has to do with self-doubt and insecurities. Learning to love yourself is an important trait to hone for your dating life, so give it a try!

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Try to pretend like your crush is just another kid at school! It’ll help tone down how nervous you are when you go over to talk to them.
Don't be afraid of rejection. If that happens, just move on.

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