Starting a Friendship
Introduce yourself. If you have not formally introduced yourself to her yet, now is the time. Introducing yourself to a shy person can be difficult. She is not likely to maintain a conversation without prompting. Use an icebreaker to get a conversation started. Bring up any mutual friends that you know you have. Say something like, “Hi, my name is Mike. I believe that we both know Joe Smith. I used to work with him.” Compliment her.
Tell her about yourself. Talk to her about your job, your childhood, and your interests. Keep it light and try to make her laugh. This helps keep the mood upbeat and take the pressure off of her to talk the whole time.
Get to know her. Ask her questions about her life. By asking her questions you are taking the pressure off of her to come up with something to talk about. You should understand that it will take some time for her to warm up to you. When she does talk be sure to listen and not dominate the conversation. Avoid small talk. Shy people tend to hate small talk.
Building Her Trust
Slowly increase the amount of time that you spend together. Shy people are often overwhelmed with too much socialization and a fast-paced relationship. Start off with talking to her a few days a week and then slowly add days over the next couple of weeks. Also, increase the amount of time that you spend together. Slowly add time to your phone conversations or face-to-face meetings.
Find a common interest that you can bond over. Once you find a subject that interests both of you, find more ways to bring that subject into your conversations. Research the subject so that you have new and interesting things to talk about.
Give her some space. Most shy people are introverts, and introverts thrive by having alone time. If she asks to be alone, that does not mean that she is mad at you. Give her the space that she needs so that she feel rejuvenated and more able to socialize.
Taking Her on Dates
Find a low-key location for your dates. Most introverts are not interested in going to a loud bar or dance club. One-on-one dates that don’t require a lot of socialization are where they will feel most comfortable. You can also spend the one-on-one time getting to know each other and building the trust that you need to win her over.
Avoid putting her on the spot. She probably understands that she is shy and might even be self-conscious about it. Don’t remind her of her shyness. Instead, help prompt subtle conversation to help her feel more comfortable. Saying things like “Don’t be shy,” will just remind her of her shyness and likely make her uncomfortable. She may not be good at making eye contact. If this is the case, avoid pointing that out, too.
Accept her for who she is. This is a very important step to any relationship. Shy people have a lot of wonderful qualities. For example, shy people are typically good listeners and deep thinkers.
Be comfortable with silence. Silence does not have to be awkward or uncomfortable. While you probably shouldn’t spend the whole date sitting quietly, you can spend moments in silence. She will appreciate that you do not need her to talk, or listen, all the time.
Building a Relationship
Move at her speed. Spend a lot of time getting to know her and letting her get to know you. Building trust is the key to a relationship with a shy girl. Ask her to do things with you that do not involve large crowds. An evening walk or a movie night at your house might be better than going out to the theater with large crowds of people.
Introduce her to your friends and family. Although she is shy, not introducing her to your friends and family could make her even more self-conscious. Just be careful not to introduce her to everyone all at once. Create opportunities for her to meet friends and family in small groups or one at a time. For example, you could go to dinner with just your parents as opposed to bringing her to a large family gathering such as Thanksgiving.
Express your interest. Though you should avoid pushing her to move the relationship too quickly, make it clear that you are serious. Many shy people are self-conscious and might not assume that you want a relationship with them. By telling her how you feel, you give her the opportunity to think about how she feels. Mention that you have feelings for her by saying things like “I do really like spending time with you. I hope to do it more often.”
Earn her trust. Shy girls often have trust issues. You will need to earn her trust and not expect it to be given freely. Be honest. Be reliable.
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