How to Talk to a Girl You Would Like to Date but Are Too Afraid to Approach
If you want to talk to a girl you'd like to date, but you're too afraid to approach her, try finding a natural reason to introduce yourself. For example, comment on the book she's holding or the class she's attending. Once you've introduced yourself, make small talk, such as about a school event or a homework assignment, to see if you get on. After you get to know her a little better, talk to her about more personal topics, like how her siblings are doing or what her interests are. Play it cool by asking her to hang out with you in a small group, or doing a relaxed activity one-on-one, like going to the mall.
Let go of your fear. Getting rid of your fear to talk to her is the most difficult part, but just remember: We are all equal, we all get nervous, and we are all human. Most girls aren't mean or rude, so if they don't want to talk to you, they won't hurt your feelings It's better approaching her and knowing the outcome, than never doing it and being left wondering what would've happened. Talk to her. Find some natural reason to introduce yourself. A good conversation starter is just getting to know her if you don't already. If she's talking to a friend, listen to (but don't stalk!) their conversation a bit, and then jump in with a witty comment like, "Hey, you like Harry Potter too!" If the girl is not talking to anyone, comment on her outfit or the book she is holding or the class she's in. Then start the conversation! If you've talked to her before, and she knows who you are then it shouldn't be too difficult. If not, all you've got to do is introduce yourself and have a conversation. Make small talk! Making small talk is a great way to get a feel for if the girl likes you or not. Making small talk could be as easy as asking about the weather, a homework assignment or commenting about a school event. Based off her reaction and response length, you can get a pretty good idea if she is interested in you. For example, if your school football team won a sectional title, you could say "Hey, did you see the game last night?". This will open up for a great conversation. If the girl says she didn't see the game though, don't press her with details about what happened and give her a play-by-play synopsis. Instead, turn the conversation toward her and ask her if she plays or follows any sports. If she sits next to you or nearby you in class, try making audible but quiet comedic remarks to her. For example, in class if your teacher is handing out a writing assignment, say something funny like "Geez, I'm scared. This looks like a lot of writing." Make it loud enough for her to hear. If she engages in conversation about your comment, that's great news! It means she was actually listening to you. If she doesn't, this could possibly mean that you were too quiet and she didn't hear you, or she was surprised you were talking to her. Keep trying though, and sooner or later she will respond. Get into conversations. Casually talk about stuff she likes and dislikes. Start by just having conversations with her. Ask her about her siblings or other little things. For example, "How are Jimmy and Sarah doing?" or, "That blue shirt brings out your eyes." Girls like it when you remember little things. Find out things you have in common, like a favorite band or sport. That will give you a common subject to talk about. If you go to school together, walk up to her in the halls and say hello after you've talked in class a couple times. You will make a good impression if you do nice things, like holding a door for her to go through or tying her shoe if you notice it has come undone. Do not go out of your way to do these things all the time. She will think it is weird instead of sweet. Become friends with her. Many guys prefer to cut to the chase, but if she is worth asking out, it is worth building a friendship. If you ask her out without getting to know her first, she might turn you down just because she doesn't know enough about you to say yes. Text her. Text or chat with her for long periods of time. Girls love it when this happens. After you've texted her for a while and you think she's good enough friends with you, try to ask her who she likes. Make sure she asks you too, otherwise it will most likely end up being a different guy. Also try to make it late—that's extra cute! Make sure that the two of you are compatible. Do you have common interests? Are you around the same age? If you are going to date this girl, make sure that she is someone with whom you actually want to spend a lot of time. It is easy to build up unrealistic fantasies in your head, but it isn't always easy to gauge whether you would truly be happy with someone. Try talking about what motivates her; by doing so, you will create a bond between you two. See if she wants to hang out in a group. Ask her and some of your other friends if they would like to go somewhere such as the mall or movies. Eventually if you two are comfortable with each other you could ask her to hang out at your house with a group of people. A group of people will make it seem less awkward. Don't ask her specifically to something and build it up. Instead, arrange something with a group of friends and say she is welcome to come along. That way, if she can't make it, no harm done and you can recover from the rejection without problems. When inviting her out, it has to be something fun that isn't a big deal for her to join in on. You want to avoid the awkward staring at your hands/feet mumbling about "what she is up to that weekend". Make sure she isn't already interested in or dating someone. If she is already dating someone, then that is her business, and you need to respect it. If she's obviously interested in someone else, then it might be worth your while to win her over—but do not get your hopes up. Play it cool, but don't make her think that you aren't interested. When you two start hanging out a lot, people will start talking and wondering if you two are dating or if you have a "thing." If people ask you about it, just say, "we like hanging out," or, "we have a lot of fun together." Never say, "we are just friends." This will give her the wrong impression. Invite her to hang out one-on-one. Ask her if she would like to hang out sometime, but don't make it sound like a date. As you spend more time with her, invite fewer and fewer people, so that eventually you can just say, "Want to hang out this weekend?" If she says no thanks, don't drop it yet. She is likely not comfortable enough with you, but she may come around if you keep talking to her. You could explain that it wouldn't be a date, just going to the movies as friends, or hanging out and going swimming. Aim to ask her out somewhere you feel comfortable. You want to find a place that is quiet, somewhat secluded, and easily accessible. Most importantly, do it in a location where you feel relaxed and confident. The better you feel about things, the more relaxed and assured you will be when you finally ask her out. Make sure she is in a good mood as well -- if she had a terrible day or seems cross, wait until she is in a better mood. Whenever possible, ask her out in person. It may be harder and more nerve-wracking, but you're more likely to succeed and can gauge her response in person. Know that you don't need a large romantic gesture to ask someone out. Movies and TV have conditioned many people to think that the only way to get the girl is a big, expressive moment. But that couldn't be farther from the truth in the real world. Simply pulling her aside after class or work, catching her on her way out the door, or sitting next to each other on the bus is enough. It is not what you do that really matters here, it is what you say. Prepare what you want to say if you feel nervous. Don't try and over-rehearse the conversation, as you cannot predict what she is going to say. However, practice keeping it brief and saying what you want to say quickly and easily. 1-2 sentences should suffice. Some ideas include: "I've really enjoyed spending time together, and I'd love to take you on a date." "Would you want to go out with me on a date this weekend?" "Let's grab dinner sometime, just the two of us?" "I really enjoy your friendship, and I'd like to try taking things a step further." Have a specific date in mind. At the very least, be ready to offer one or two days that work for you. Asking with specifics is a much better way to gauge her answer. If she wants to go on a date, have a suggestion ready: "Great! How about dinner on Thursday?" or "There is a great play Saturday at 8 I was interested in, want to join me?" Have at least one back-up date in case she is busy, or ask her when a good time is if that fails too. Go ahead and say it, even if it feels awkward. And the end of the day, you just have to blurt it out. It is not easy, but it is the only way to do it. Keep it short and to the point. "I really like you, and I'd love to go out on a date sometime," should suffice. Remember why you want to talk to her, and know that any answer is better than sitting and waiting for one. Count to 3 and make yourself ask when you get to zero. Avoid talking too much beforehand. Say hello, ask how she is doing, then get right to the point. The longer you wait, the colder your feet are going to get. Once you know you want to ask her out, you need to go ahead and do it. Be honest. If she is going to ditch you because of a little initial awkwardness, is she worth dating? Just be yourself and put yourself out there, even if you are nervous, awkward, weird, or uncomfortable. Do you best to launch into the conversation. "I'm a bit nervous to say this, but..." "I know I seem kind of awkward, but I want you to know how I feel." Relax and go slowly. Take as much time progressing the "dating" relationship as you did progressing the 'friend' relationship. You don't need to dive into anything. 
Let go of your fear. Talk to her. Make small talk! If she sits next to you or nearby you in class, try making audible but quiet comedic remarks to her. Get into conversations. Become friends with her. Text her. Make sure that the two of you are compatible. See if she wants to hang out in a group. Make sure she isn't already interested in or dating someone. Play it cool, but don't make her think that you aren't interested. Invite her to hang out one-on-one. Aim to ask her out somewhere you feel comfortable. Know that you don't need a large romantic gesture to ask someone out. Prepare what you want to say if you feel nervous. Have a specific date in mind. Go ahead and say it, even if it feels awkward. Be honest. Relax and go slowly. 