How to Start a Conversation with Your Crush Without It Being Awkward
To start a conversation with your crush without it being awkward, talk in a warm, friendly manner to help you both feel at ease. For example, you might say “Hi, I don't think we've actually met yet. I'm Tim, how's it going?” After introducing yourself, try chatting with your crush about their interests. Or, if you have a class together, you can say “So, how's your midterm paper coming together for our English class?” In order to avoid awkward silences, have a few open ended, easy topics ready to talk about, like asking your crush their opinion on what's for lunch that day or if they like the new art teacher. If the small talk is going well, then move on to some deeper questions, like your crush's interests, hobbies, or work. While your crush is talking, be an active listener by repeating a few of the main ideas they talk about and avoiding interruptions to show that you care about their thoughts.
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 if there are any dances, parties, or school events that are coming up that you can start a conversation with him or her at. Talk to your crush like you already know him or her. One way that conversations can become awkward is when one person is extra stiff with the other person; treating him or her 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 him or her with warmth and a friendly tone.  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 him or her as though you have a history you do not have. For example, you wouldn't say “Hey dude. How's it?”. Think about what he or she might be interested in talking about. If you are familiar with your crushes interests, life, friends, likes, dislikes, etc., use that knowledge to your advantage. You don't have to focus on those things in particular when you talk, but you can talk about things related to his or her interests. For example, if you know that he or she loves 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 him/her at all when that is not true. 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.  If you are going to a dance or somewhere you might be up close and personal with him or her, 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. 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.  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. Get the update on something he or she has 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 thing 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 he or she knows. If you want to remind him or her, 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 he or she doesn't know, you mentioning the class first will tip him or her off and he or she will probably apologize for not recognizing you. Ask for his or her 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 him or her something that you do or know and then ask his or her 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?”  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 him or her something too controversial. Stay away from any hot button topics like politics or religion. Ask him or her 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. You can ask your crush something unusual but fun. For example, you could ask him or her 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 he or she tells you his or her celebrity look alike, you can say whether you agree or disagree, and you can tell him or her 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 he or she has already used many times before. This kind of playful conversation helps you get more comfortable with one another. 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.  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 him or her- the important part is continuing the conversation. Sometimes just going with your gut can bring out your most confident self. Ask questions about his or her interests, hobbies, or work. Once you have established a good connection with your crush, you should start trying to get to know him or her better. Start with something that he or she has 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 him or her. Then ask follow up questions. For example, if he or she is 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 he or she doesn't seem too excited about his or her books, you can move onto something else more open ended. Say something like, “So what else are you up to this week?”. Avoid bring 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 he plays soccer, avoid bringing that up directly. Don't say “So tell me about your soccer season.” Instead, let the conversation get there naturally. Be an active listener in your conversation. Your crush will enjoy him/herself 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 his or her 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 him or her know that you are listening and will give him or her the chance to clarify anything. Repeat the most meaningful parts of what he or she is 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 him or her feel connected to you because you show that you understand important things about him or her. Avoid interrupting him or her in conversation. It is easy to get excited by what we want to say and interrupt during his or her turn in the conversation. But resist the temptation and wait until he or she has finished talking, and then show your enthusiasm for what he or she is saying. Be empathetic. If your crush talks about something hard that is going on with him or her, make sure you don't skip over his or her feelings in the conversation. You could say in response to him or her talking about failing a test, something like, “I could understand why it would be really frustrating to have to retake that test.” Show him or her 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 him or her. 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. Make a plan to hang out again, and/or get his or her number. If things seem to be going well, ask your crush if he or she wants to hang out again or ask for his or her 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 his or her 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 his or her 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 to him or her to hang out. Bring the conversation back to something you already talked about. You might want to talk to your crush about something he or she 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. 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 him or her that you enjoyed your 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 him or her 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 him or her about the things you talked about. 
Wait for the right time and place to start a conversation. Talk to your crush like you already know him or her. Think about what he or she might be interested in talking about. Freshen your breath before you talk. Make a funny or playful comment about the place you are at or thing you are doing. Get the update on something he or she has been doing, especially if you share something in common. Ask for his or her opinion on something easy to talk about. Ask him or her something unexpected but easy to answer. Go with an opening line that pops in your head. Ask questions about his or her interests, hobbies, or work. Be an active listener in your conversation. Show him or her that you are enjoying yourself in conversation. Make a plan to hang out again, and/or get his or her number. Bring the conversation back to something you already talked about. End the conversation on a good note. 