Asking Out a Shy Girl
Start by saying hello regularly. If you've got a crush on a shy girl, it can be hard to approach her at first. So just take little steps. Don't ask her out right away. Instead, start by saying "hi" on a regular basis. Whenever you pass each other in the hallway, make eye contact (this might be hard) and smile. Use her name, and greet her in a friendly way.
Find out a little more about her. Friend her on Facebook, or other social networking sites, to learn more about your crush. Talk to her friends to find out if she's dating anyone, or what kind of people she likes to date. Try to learn about her hobbies, how she spends her free time. Learn what she likes. Often, shy people will feel more comfortable talking online, or texting. Becoming online friends first is a great way to get to know a shy girl. Don't assume girls who act shy around you like you, or don't like you. Shyness isn't a sign of anything except being shy.
Introduce yourself. If you want to date, you need to do more than say "Hi" and scamper off. Once you feel like she's comfortable enough with you saying hi to approach her, just walk up to her some time and have a short conversation. Make sure she knows who you are before you ask her if she wants to date. Keep it simple: "Hey, my name is _____, we have Biology class together."
Talk one-on-one. Shy people are often quite good at one-on-one conversations but struggle in big groups. Don't try to engage a shy girl in class, or while you've got four of your friends with you, or it's going to be rough. Bring up something simple to talk about, something that you know you have in common, and have a short one-on-one conversation. If you're in class together, just talk about class: "I really messed up that last test. It was so hard. How'd you do? Do you like this class?" You could also arrange to talk one-on-one at a later time. For example, you could say something like, “Hey, do you have a minute to talk right after school gets out? I have a question to ask you.”
Keep your talk brief. Lots of shy people fear that they're "bad" at having conversations, and don't like to talk because they're afraid of messing it up or being awkward. This usually makes it worse. Instead of drawing it out, just exchange a short little chat and then break it off. Say, "Hey, good talking to you. See you later!" If it seems like she feels uncomfortable, don't draw extra attention to it. Just end the conversation in a friendly way, with a small compliment. "It's so good talking to you. You're funny. Let's talk again soon."
Ask her out in a simple way. Keep talking to this girl. Have your little conversations, making them gradually longer and longer. When you start to feel comfortable talking with her, just ask her out. Keep it simple and keep it short: "Hey, I've always noticed you and I think you're a really sweet and really nice person. I like you a lot. Would you like to go out with me sometime?" Sometimes, things like dances or other big events can be intimidating for shy girls. It's actually sometimes better to just keep it vague: "Would you like to go out sometime" might be better than, "How about this Friday?" You can also ask her if she would prefer a social event or something quieter. For example, you could ask if she’d prefer to go to an upcoming dance, or just go to a coffee shop and talk. It's always better to ask directly rather than indirectly! This way, you'll both be on the same page.
Dating a Shy Girl
Make plans ahead of time. If you call up a shy girl out of the blue, it's possible that she'll give you an excuse to avoid going out. This isn't because she doesn't like you, but because introverted or shy-types like to have their plans in place. Shy girls need a chance to get ready mentally for a date. If it's 4:30 on a Friday night and a shy girl doesn't have plans, she's probably looking forward to a quiet night at home. Make your plans ahead of time to give her enough opportunity to prepare. In general, try to make plans at least 1-2 days ahead of time at least.
Plan fun dates that will get her to open up. It's good to plan an activity for a date with a shy girl, so you'll have something to do together. If conversation is going to be hard, try to pick an activity that'll let her loosen up and have a good time, without having to do a lot of talking. Going for a bike ride, bowling, or playing mini golf might seem like silly ways to go on a date, but it's a good way to keep yourself active and busy. You'll have a fun shared experience. Dinner is a good opportunity to talk, but it might end up being pretty awkward if you have a hard time talking together. Alternatively, movies mean you can't talk at all. Not the best choices. Make sure whatever you do is quiet enough for her to talk if she wants to. If you go to a booming club with loud electronic music, you'll never be able to talk.
Spend your downtime together too. Shy girls aren't generally big partiers. If you ask a shy girl if she wants to go to a big dance, or to the football game, or to a loud dance club, don't be offended if she'd rather stay in and watch Netflix on the couch with you. Make the time that you're together special, even if you're not doing something that sounds like a date. Cook dinner together, instead of going out to a fancy new restaurant. This gives you the chance to do an activity that will get you talking, even if you're just talking about the chicken and rice dish you're making together.
Make your dates one-on-one. Shy girls are often intimidated by large groups, but you can always ask her about her preferences. While it might sound great to you to hang out with all your friends and watch football together in a huge group, it might be her worst nightmare. Try to give yourself some private time. Of course, some girls might be more comfortable in group dates and feel more shy one-on-one. All girls are different. Talk to her and find out what she prefers and do what makes her feel comfortable. If you do go to a dance or some other kind of social event, come up with a signal that she can give you if she wants to leave or pick a designated time leave.
Let her pick the plan. Being shy doesn't mean that she doesn't have a strong opinion. When you're going out, give her the opportunity to pick the activity. This will help her feel comfortable and confident that you enjoy being together. Give her the opportunity to open up. Don't be afraid to take charge, though. Some shy girls might give you a lot of "I don't know" answers when you ask what she'd like to do on Friday night. Have a plan in place, if she doesn't. You should also offer more than 1 option to ensure that she can pick what she feels most comfortable doing.
Keeping Shy Girls Happy
Compliment her. Shy girls are often, but not always, somewhat self-conscious. But even if a girl isn't self-conscious, it's a good idea to offer compliments to make her feel comfortable and loved. Keep them simple and genuine to make a shy girl feel more confident around you. If she does, she'll open up more and be less shy in some cases. Don't pile it on, just keep it simple, and make it something that she has control over, not something abstract about her looks. "Your eyes are pretty" might be nice, but "I love your hair like that" is a great one, because she did her hair. You're complimenting her choice, not her looks. Make sure to compliment her personality traits as well, such as her intelligence, sense of humor, etc.
Give her some space. Shy girls or introverts often need a lot of private time, and won't want to spend hours and hours texting with you or talking on Facebook. That's ok. It doesn't mean she doesn't like you, or that she's about to dump you. It just means she's being who she is. Relax and move at her pace. If you call or text her and leave a message, don't get in touch again until she responds to it. You left the message. She'll get it. Let her decide how much of your relationship to share on social networking. Don't put up a bunch of pictures and updates about what you're doing together unless she wants to. Shy people might want to be more private than you're used to.
Don't force conversations. The secret to dating a shy girl? Talk less. Shy girls will just want to be quiet sometimes. That's ok. Learn when to pull back and just be quiet. She'll open up and talk more when she's ready. Just enjoy being together. If it's quiet because you don't have much to talk about, just enjoy sharing silence together. There's no need to constantly talk. It may even turn her off. You can even tell her that you like sharing comfortable silences with her if you think it might put her at ease. Don't ask her why she's shy. Sometimes people will ask this question when they're feeling awkward. Drawing attention to it only makes it worse. There's no good answer to this question, and she'll just withdraw more.
Ask her questions. If you struggle to get a shy girl to open up and talk more, maybe it's because you’re not talking the right way. Ask her genuine, specific, and open-ended questions to get her to feel more comfortable and open with you. Listen to her answers and follow up with more questions. This has the added bonus of allowing you to get to know each other better. Encourage her to talk more by asking follow up questions. If she mentions that she loves going to the lake, that's an opportunity to learn more. How long have you been going? What do you like to do there? Keep questions open-ended to give her the chance to talk more. Don't ask, "Did you have a good soccer game last weekend?" because that only has a one-word answer. Instead, ask, "How did you feel about the soccer game last weekend?" Make sure to share some things about yourself as well. She might be too shy to ask you, so it’s okay to volunteer this information.
Give her the chance to talk. It's important to be a good listener. If you're used to waiting for your own opportunity to speak, you might find it hard to talk with a shy girl. Use good listening skills and give her the chance to open up and share her life with you. Look her in the eyes while she's speaking. Nod along and encourage her when she's talking. Put away your phone and other distractions. Give her your undivided attention.
Go slowly. Never rush a shy girl, or you'll lose her. Dating needs to move at a slow pace, letting her dictate the tempo of things. Shy girls need to feel comfortable, relaxed, and free with someone that they date. Let her decide when she feels comfortable enough. If you want to move in for a kiss, but you're not sure whether or not it's appropriate, the best way to know is to ask her first. "You look so pretty tonight. I'd like to kiss you. Is that ok?" Don't try to "cure" her. There's nothing wrong with being quiet, shy, or introverted. If you want to change someone to date them, you shouldn't be dating.
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