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Approaching Her
Find an appropriate time to strike up a conversation. If she's cramming for a test before the bell rings or having an intense conversation with a friend, it's probably best to wait. Find a time when she's alone and doesn't look like she's in a rush to get anywhere, such as in the cafeteria or after school lets out. If she's constantly surrounded by friends, don't be afraid to say, “Can I talk to you for a second?” See if you have any common interests. Is she apart of the debate team? You could try it out too as a built-in way to meet her. If there are breaks or club outings, you could try to strike up a conversation during those times.
Avoid awkwardness by preparing an opener. Don't spout off a cheesy pick-up line the second you're face-to-face, but have a general idea about what you're going to say. This can be as general as a question about her day, or you can cut right to the chase and tell her you're interested. Either way, it's great to have an idea going into the conversation so that you aren't faced with awkward silence. You could say something like, "Hi [name]! Happy it's almost Friday?" If you see her holding a specific textbook or going into a classroom, you could ask her about that. "Hey [name], you have history with Mr. Smith? I heard he's great, do you like him?" A general rule of thumb is to talk to her as if you already know her. This doesn't mean you should act like you're best friends, but don't act like you're talking to your teacher or principal. Say something like, "Hey [her name], how's your week going so far?" rather than, "Hello [name], how are you today?"
Be confident. Even if you've planned out a perfect opener and have a great idea about what you want to talk to her about, you need to also convey confidence with your body language. Keep your head up, and make eye contact with her. Make sure you're standing up straight, and take a wide stance so that you look secure in your space. Take care not to wring your hands or nervously fiddle with your clothes or backpack. If you feel nervous, that's perfectly normal. The trick is simply not letting it show. It sounds silly, but practice your stance in the mirror before you approach her. Make sure you notice your nervous habits, and work on correcting them. You could also try making a practice video with your phone to hear how you will sound when speaking to her. Take note of any times you looked or sounded nervous & practice again until you are comfortable. Delete the videos when you're done if you want to.
Pay attention to her social cues. If you thought she was free when you grabbed her to talk but you see her checking her watch or angling her body to the closest exit, she probably has somewhere to be. That's OK, though, because you don't need to talk to her for hours to ask her out. Try saying something like, “I'm sure you have somewhere you need to be and I won't hold you up, but I wanted to see if you're free this weekend to grab dinner.” This is short, sweet, and straight to the point. You asked her out while at the same time showing her that you respect her time. If she seems uncomfortable or in a rush, respect that. Don't ruin your chances with her by forcing a conversation when she can't talk.
Using Flattery and Common Interests
Compliment her. If you don't know her well (or at all), be brave and tell her why you approached her. If you think she is really well spoken in English class, tell her that. If you think she's really beautiful and you'd love to get to know her personality, tell her that. “Playing it cool” can work sometimes, but if you don't know her at all, you should lay your cards on the table. A good, respectful compliment is almost always appreciated. This will help her see you in a positive light right off the bat. Be genuine with your compliments. Don't just give her the compliments you think most girls would want to hear. What do you truly, genuinely like about her? If it's welcoming smile, tell her that. If it's her confidence, tell her that. If she can tell that your compliment is coming from your heart, it will mean much more.
Find common ground. Whether it's one class you share, the neighborhood you live in, or a mutual friend, use it to strike up a conversation. If you can't think of anything specific that you have in conversation, you can even comment on the weather! Any shared experiences are helpful to get the conversation rolling, and to help make her feel more relaxed. If you truly cannot think of some similarity, that's fine. You can always ask her a question about something she is interested in that you're not familiar with.
Be authentic. The overused cliché to “be yourself” is so important in this situation. If the girl can tell you are being genuine and putting yourself out there, she will be much more likely to reciprocate. If she thinks you're trying to play a part or act like a person you aren't, she will have her guard up too. Not only does this make you look endearing, but it also saves you time! What's the point of going out with a girl who doesn't like your true personality? You can't act like someone you are not for very long.
Make a connection. If you don't have much in common or any overlap with your social activities or circles, create common ground. Try talking about an upcoming school event, like school play, a party, a sporting event, or anything you think she might be interested in. You could also talk about something in the news. The important thing is to find something, anything, to connect on, so that she can walk away from the conversation with a specific memory. Asking her how she is and saying you're looking forward to the weekend is fine, but connecting on a specific topic will add much more substance to the conversation.
Asking Her Out
Invite her to something specific. “Do you want to hang out sometime?” is much different than, “Would you like to see a movie on Friday night?” If you are vague with your invitation, she can be vague with her answer. Instead, give her a specific event that you'd like to take her to, and she can give you a concrete answer. Not only will this help “set things in stone,” but it will also show her that you took the time to plan ahead and decide on a great date for her.
Find a time that works for her. If you give her a specific time and she is already busy, ask her if another time works for her. This will show her that you're flexible, and also that you're very enthusiastic about the idea of taking her out. Don't give up if your original plan doesn't work with her schedule– let her pick a time that works for her. If she says she needs to check her schedule or get back to you, let her do just that. You can simply end the conversation by saying, “I'd really love to take you out, so please let me know when you're available!” You've done everything you can do, and the ball is in her court.
Keep things casual. You are not proposing marriage, and your life doesn't hang in the balance. You are simply asking her if she would like to get to know you better. If she says no, that is okay. You can always leave it open and get to know her better as friend. If you two become friends first, she may be more comfortable going on a date with you. Or you could move on, and find another lucky lady to ask out. If she says yes, fantastic! Take her on a date and see if you connect. Just remember, you will survive no matter what happens. If you are nervous, sweating bullets, and acting like this is the most serious thing you've ever done, she will probably be a little intimidated. Keep the mood light and cheery, and she will feel much more at ease around you.
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