How to Ask a Shy Girl Out

Getting to Know Her

Try to make her laugh. When getting to know a shy girl, it’s important to make her feel comfortable around you. She will be more willing to open up to you if you make her feel comfortable. An easy way to do this is to make her laugh. Tell jokes and act goofy, but don’t make fun of her. Make sure your humor comes from a place of kindness and isn’t cruel to anyone. If you’re in school together, make jokes about the class or school in general. Friendly joking, especially if it’s complimentary, is a great way to break the ice and help someone overcome their self-consciousness.

Avoid pointing out her shyness. Her shyness or quietness may be a predominant part of her personality, but it is best not to point it out to her; she is likely very aware of it. Poking fun at her shyness or asking her why she doesn’t talk more could make her become even quieter. Instead, encourage her to talk about herself.

Ask her questions about herself. Conversation may be difficult for her at first, so try to initiate a conversation by asking her questions about herself. Choose questions that she can easily answer as these might encourage her to open up to you. Ask her about her interests, dreams for the future, her childhood, and what her family is like. Try to ask follow-up questions to show that you are really interested. For example, if she says that she would like to be an engineer one day, ask her exactly what type of engineering she’d like to go into. If she tells you something interesting about herself, respond in a sincere, complimentary way. For example, if she tells you she wants to be an engineer, say, “Wow, that’s so awesome!” Don’t push her if she doesn’t seem to be comfortable with a question.

Chat with her regularly. Once she begins to open up to you, try to have regular conversations with her. This way, you can form a friendship with her. You can talk about simple things, like homework or how her day was. While she is talking, be a great listener and be supportive of the things she tells you. Don't interrupt her. Let her say what she wishes to say at her pace. Talk only a little about yourself. She can find out more later, and a little mystery is a great thing. Reader Poll: We asked 483 wikiHow readers who've gone on a date with a shy girl, and 74% of them agreed that the best way to ask her out is by getting to know her as a friend first. [Take Poll]

Make an effort to spend extra time with her. Along with having regular conversations, spend time with her as much as she feels comfortable with. You can be study buddies, and pick each other's brains for ideas and solutions to schoolwork or college assignments. Or, you can attend a performance, games of hers, or whatever activity she enjoys to show your support. Sit with her in the cafeteria at lunch and simply chat about everyday life. Compliment her on her reading choices and talk about books together.

Get to know her friends. They will be a useful source of support and information as you get to know each other better. They can also serve as a source of reassurance to her, helping her to realize that you mean well and are worth letting down her barriers for. You should, however, show that you are genuinely interested in her friends instead of acting like you just want to impress the girl you’re interested in. Ask if you can join her when she is hanging out with her friends. Don’t push it if she says no. She might think you like one of her friends if you put too much emphasis on spending time with them. Try to spend time with them only when she is around—at least at first. Say positive things about her to her friends.

Asking Her Out

Wait until she is alone. Asking her out while she is in a group or around people in general may embarrass her. Instead, wait until you have the opportunity to spend some time alone together. It should be your goal to make her feel as comfortable as possible when you ask her out.

Approach her in a casual manner. At this point, you should have built up some kind of relationship with her. Act like you usually do around her. Acting too nervous or overbearing could make her feel uncomfortable. Approach at a time when you normally see her. If you want to make the moment special, you could ask her to go for a walk in the park first

Start with a compliment. This is an easy way to give her an idea that you like her and think highly of her. You can compliment her looks by saying “You look beautiful today.” Or, you can compliment aspects of her personality. For example, you could say “I think you are incredibly smart and kind.” Don’t overdo the compliments. One or two nice compliments to begin with is enough.

Ask her to go a date with you. You can ask her as casually or as formally as you’d like. If you want to be casual, say something like "Hey we can grab dinner later if you aren’t busy.” If you want to make sure your intentions are clear you can say, “I’m really starting to like you, and I would like to take you out on a date if that’s okay with you.”

Give a positive reaction to her answer. If she says no, simply back down and say maybe another time. If she says yes, act pleased and make plans. Either way, you should react in a way that makes her feel comfortable. Don’t be angry with her if she says she’s not interested.

Taking Her on a Date

Take her somewhere quiet. Taking her to a party is probably not the best date idea for a shy girl. Instead, take her somewhere quiet where she can open up to you. For example, take her for a walk in the park or to a picnic in the park. If you aren’t sure what she’d want to do, you can ask her if there’s somewhere she has been wanting to go.

Go out for ice cream or a movie. If the park is a little too quiet for her, you can suggest going out for ice cream. It’s stress-free and there are some people around. A movie is another low-key date idea because it’s something you can do together without feeling the pressure to talk. If she doesn’t like ice cream, suggest going out for lunch or dinner.

Take things slowly. Even if the date goes very well, do not move very fast with a shy girl. Moving too fast could be overwhelming for her. For example, don’t go in for a kiss without asking permission. If you feel like she’s having a good time with you, ask if she’d be okay with holding your hand. You can move on from there if she seems okay with holding your hand.

Ask her to be your girlfriend. Depending on how the date or dates go, you may want to ask her to be your girlfriend. First, try to get an idea of how she feels about you. You can ask if she enjoys spending time with you. Or, if she has opened up to you a lot, ask her if she likes you in the same way that you like her. If she does, ask if she would like to be your girlfriend. For example, you could say “I’ve really enjoyed getting to know you. I’ve come to like you a lot, and I was wondering if you would like to be my girlfriend?”