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

Co-authored by Erika Kaplan

Having a not awkward conversation with your crush is possible and can be so fun that it leads to more hanging out. Learn about how to talk to your crush like to a friend, without sweating in winters. Make playful comments, and ask your crush unexpected but easy questions that lead to funny connections. Even if awkwardness happens in your conversation, have a good conversation that leaves your crush wanting to talk to you more.

Sample Conversation Topics

Sample Ways to Talk to Your Crush

Sample Conversation Topics to Avoid

Part 1

Part 1 of 3:

Before You Start a Conversation with Your Crush

1
Wait for the right time and place to start a conversation. A lot of awkwardness can be avoided if you can 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, or after school or after an event is over. Use down time as an opportunity to start a conversation, and be cool about it. A good place to talk could be at a bus stop, in a bus or on public transit, in a lunchroom, at a dance, or at a get together.
- Make sure you have enough time for at least a few minutes of conversation. There are some down time periods that are too short for a conversation. An example of a bad time to talk to someone would be if class is about to start. This is probably not a great time to try to have a conversation because you will be interrupted and will feel silly that you tried to start a conversation at that time.
- Avoid trying to start a conversation in a line or during a passing period.
- Think about the way your schedule and your crushes’ schedule overlaps. Plan on starting a conversation when both of you are free.
- Are there any events that are coming up? Think about whether there are any dances, parties, or school events that are coming up that you can start a conversation with them at.
2
Talk to your crush like you already know them. One way that conversations can become awkward is when one person is extra stiff with the other person; treating them like a stranger. Instead, treat your crush as though you are already friendly with him or her. Even though it may be true that you do not know your crush well, you should still talk to them with warmth and a friendly tone. ^{[1]
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Research source} You can even start a conversation with an introduction while using a tone of familiarity and warmth by saying something like, “Hi, I don’t know if we have actually met. I’m Tim, how’s it going?”
- When you are talking to your friends, try to notice your tone of voice, the hand gestures you use, and the kind of expressions you use. When you are talking with your crush, try to be the same kind of natural and relaxed while you talk.
- Don’t be overly familiar with them as though you have a history you do not have. For example, you wouldn’t say “Hey dude. How’s it?”.
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3
Think about what they might be interested in talking about. If you are familiar with your crush's interests, life, friends, likes, dislikes, etc., use that knowledge to your advantage.^{[2]
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Expert Source

Erika Kaplan
Matchmaker
Expert Interview. 1 October 2020.} You don’t have to focus on those things in particular when you talk, but you can talk about things related to their interests. For example, if you know that they love the beach, you can talk about the surfing you have done recently. And you don’t have to mention that you know that the person likes the beach. Just talk about it like you would talk to a friend who loves the beach.
- Awkward conversation can happen when you pretend like you know more about the person than you do in the same way that it can become awkward when you act like you don’t know anything about them at all when that is not true.
4
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 with xylitol to take with you to school or wherever you meet your crush. Sugarless gum will cause your mouth to make saliva which will in turn make your breath better and make it easier for you to talk. Pop a piece in your mouth 5 minutes after a meal and a few minutes before you talk with your crush. ^{[3]
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Research source}
- If you are going to a dance or somewhere you might be up close and personal with them, you can gargle with a mouth wash after you brush your teeth to freshen your breath.
- Avoid eating food that will make your breath smell like onions and garlic.
- Drink a glass of water, this will flush out any of the food and bacteria that make for bad breath.^{[4]
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Part 2

Part 2 of 3:

Starting and Having the Conversation

1
Make a funny or playful comment about the place you are at or thing you are doing. Use your comment as an icebreaker to start the conversation. Look around and observe what is going on around you. Is there anything funny or interesting that you notice? For example, if it is lunch 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?” If you are going to remark on something simple, try to make it playful. Even if you don’t think of yourself as a funny person, you can still be playful. And playfulness is found to be very attractive to both guys and girls. ^{[5]
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Research source} This playfulness will make the conversation fun and will help keep the mood light.
- Don’t worry, the first few comments you make to your crush are not going to make or break the conversation. Getting the conversation started is more important. So don’t worry too much about being smooth, and focus instead on continuing conversation.
2
Get the update on something they have been doing, especially if you share something in common. Once you have broken in with an opening line, move on into something you can talk about more. Asking for an update is a good question to ask if you do already know the person a little bit or you are taking a class together, for example. It is a good idea to acknowledge your familiarity with one another by talking about the things you have in common. This will make the conversation less awkward, and you will also get a better understanding of what is going on with the other person in your shared thing. For example, if you are taking a class together you can say, “So how is your midterm paper coming together?”
- You don’t have to mention the fact that you are in a class together unless you aren’t sure that they know. If you want to remind them, do it without making a big deal out of it. Say “So in English class, how is your midterm paper coming together?” It is not weird that you know that you share a class. If they don’t know, you mentioning the class first will tip them off and they will probably apologize for not recognizing you.
3
Ask for their opinion on something easy to talk about. Topics of conversation can go by pretty quickly, and so it can be good to have a couple of open-ended and easy to answer questions lined up to ask your crush. You can start by telling them something that you do or know and then ask for their opinion on it. This question can also be related to the context of where you are or what you are doing. For example, if you are 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 of apple is your favorite?” ^{[6]
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Research source} Once again, being playful is a good way to make your conversation less awkward and more fun, especially when you are talking about simple topics and just getting your conversation going.
- You don’t want to ask them something too controversial. Stay away from any hot button topics like politics or religion. ^{[7]
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4
Ask them something unexpected but easy to answer. You should try to make a unique connection based on your conversation and the particular person you are talking to. ^{[8]
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Research source}You can ask your crush something unusual but fun. For example, you could ask them something like “Is there a celebrity that people say, or you think, that you look like?”. This kind of question could make him or her laugh. Once they tells you their celebrity look alike, you can say whether you agree or disagree, and you can tell them who your celebrity look alike is (and you can lie as a joke).
- Avoid small talk or getting to know you questions. You don’t want to ask questions like “So where are you from?” because you will get an answer they have already used many times before.
- This kind of playful conversation helps you get more comfortable with one another.
5
Go with an opening line that pops in your head. If you don’t have many opportunities to talk to your crush and you see a good one, even if you don’t have everything mapped out, you may want to seize the opportunity to talk to him or her by just going for it. ^{[9]
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Research source} Part of having a crush will always involve some amount of awkwardness and that can be part of the fun. So you don’t have to overthink it- go for it.
- Going for it is good because it will help you get over the barrier of initial contact. And remember, it isn’t very important how you start talking to them- the important part is continuing the conversation.
- Sometimes just going with your gut can bring out your most confident self.

Part 3

Part 3 of 3:

Keeping the Conversation Going

1
Ask questions about their interests, hobbies, or work. Once you have established a good connection with your crush, you should start trying to get to know them better. Start with something that they have mentioned or that you have observed in your interactions. For example, “I see you have some books with you, what are you reading?” This is a low pressure question that lets your crush know you are interested in them. Then ask follow up questions.
- For example, if they are excited to talk about the books, ask more questions/make connections related to the books. For example, “That is cool that you are reading that book. My favorite book by that author is ______.”
- Or, if they don't seem too excited about books, you can move onto something else more open ended. Say something like, “So what else are you up to this week?”.
- Avoid bringing up topics of conversation that show that you already know about your crushes’ interests because that might make you feel awkward. For example, if you know they play soccer, avoid bringing that up directly. Don’t say “So tell me about your soccer season.” Instead, let the conversation get there naturally.
2
Be an active listener in your conversation. Your crush will enjoy themself in a conversation with you much more if you are a good listener. Once you have started conversation, you should be face to face or in a listening position where you hear and see their face easily. Another key part of active listening is making consistent (but not constant) eye contact during your conversation.
- 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 might keep you from really hearing what your crush is saying.
- Repeat the main idea of what your crush is saying. This will let them know that you are listening and will give them the chance to clarify anything. Repeat the most meaningful parts of what they are saying. For example, you can say “So are you saying that you are new to painting but it feels like you have been doing it forever?”. This will help them feel connected to you because you show that you understand important things about them.
- Avoid interrupting them in conversation. It is easy to get excited by what we want to say and interrupt during their turn in the conversation. But resist the temptation and wait until they have finished talking, and then show your enthusiasm for what they are saying.
- Be empathetic. If your crush talks about something hard that is going on with them, make sure you don’t skip over their feelings in the conversation. You could say in response to them talking about failing a test, something like, “I could understand why it would be really frustrating to have to retake that test.”
3
Show them that you are enjoying yourself in conversation. One way to keep a conversation friendly and natural is if you seem like you are having a good time talking with them. A few ways you can show this if you make eye contact, smile often, laugh, lean forward slightly when you are talking, and use open body language. Use any gestures when you talk that are natural for you, and keep your arms open and not crossed.
- Tilting your head to one side is another good way to show friendliness/playfulness when you are talking and flirting.
4
Make a plan to hang out again, and/or get their number.^{[10]
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Research source} If things seem to be going well, ask your crush if they want to hang out again or ask for their number. This is good to do around the three quarter point into your conversation. It is a good idea to suggest getting together or getting their number after you have made solid connections and before the conversation has become tired or worn out. Think about a couple of activities that would be right for you both before you have a conversation. Say something like, “You are really cool, would you want to hang out sometime?” Then suggest a couple of things you can do together and get their number.
- Or if you want to play it safer, you can simply ask “Hey, can I have your number? I have really enjoyed talking to you.”
- If you feel like the conversation was just okay, you can always wait for a couple more conversations through texting or in person before asking them to hang out.
5
Bring the conversation back to something you already talked about. You might want to talk to your crush about something they have talked about at the beginning of the conversation. For example, you can say, “So how much longer do you think you need to spend on your midterm paper?” And then spend the rest of the conversation finishing talking about the points of conversation you have already started.
- You can 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 is a good way to make your connection last past the first conversation.
6
End the conversation on a good note. When you are feeling good and you have just finished laughing about something, you should politely end your conversation so that your crush is left with a good impression. Make sure to tell them that you enjoyed the conversation.
- You can keep the end of your conversation casual. You can say something like, “I should be getting home now, but I had a lot of fun talking to you.”
- If you are going to be seeing your crush in the future you should say something about seeing them again. Say, “I look forward to seeing you in class and hearing how your paper turned out.”
- Send a follow up text in the next couple of days saying hello and checking in with them about the things you talked about.

Expert Q&A

Question

How do you respond when your crush compliments you?

Erika Kaplan
Matchmaker
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

Matchmaker

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.
Question

Why is it hard to accept compliments?

Erika Kaplan
Matchmaker
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

Matchmaker

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!