Approaching Her
Don’t make assumptions. It might be tempting to think she has low self-esteem or is boring. However, many shy girls are very self-confident and enjoy doing exciting things. Keep this in mind before you approach her and throughout the beginning of the relationship. Treat her as an individual, not a stereotype.
Approach her by yourself. Shy people usually don’t like being the center of attention. If you walk up to her with your friends, she might feel overwhelmed and uncomfortable. Make the first introduction a one-on-one event.
Avoid overly crowded places. Shy people usually don’t like attention from too many people at once. At the same time, they usually like to be able to reach out for help if they feel unsafe. Approach her when fewer people will be around. Some possible times and places are: At the end of the day, as you’re walking to the bus stop. After class at the local café.
Introduce yourself. Maybe you know her name, but you’re not sure if she knows yours. Start with something like, "Hi! You're Emma, right? I'm Joe. Nice to meet you!" On the other hand, if you don’t know her name, you could try, “We pass each other everyday, but we’re always rushing in opposite directions. Now that we have a few minutes, can we talk? I’m Joe, by the way. And you are…?”
Smile. Frowning might turn her off because it can make you look unfriendly. She’ll likely react more positively to you if you smile. Even if you’re feeling a bit down, a simple smile can brighten the mood and keep her engaged in the conversation.
Respect her feelings from the outset. Acknowledge that shy people usually don’t think of their shyness as a problem. In the beginning, she probably won’t want to say too much, or she might speak with a soft voice. Show consideration for her preferences. Don’t ask her to “speak up” or make puns about her personality.
Starting a Conversation
Start small and gradually build up. Aim for short conversations at first, say 5 to 10 minutes. Don’t expect to talk to her too often in the beginning. Weekly conversations are perfectly okay. As time passes, gradually increase how long and how often you talk. There are no set rules in how and when to take these steps. Let the relationship develop naturally.
Act natural. When you're acting natural, it’s easier to keep the conversation flowing. Take deep breaths and speak at your normal pace. Speak loud enough for her to hear but not so loud that she’ll feel uncomfortable. Use relaxed, slightly animated, body language.
Pick a friendly icebreaker. In all likelihood, you’ll likely have to start the conversation. Ask her about her hobbies, favorite books, or sports. Just avoid making the conversation all about her, or she might feel overwhelmed. You could say: “I really like that guitar pin on your backpack. Do you play?” From here, you could segue into favorite musicians or your shared appreciation of music in general. (After looking at the cover of the book she’s reading): “Oh, you have a copy of 1984. I feel like I’m the only one who’s never read it. I’d like to hear your opinion.” This way, the spotlight will be on the novel, as opposed to her.
Pause every so often. After you’ve broken the ice, she might become quiet. Don’t use this as an excuse to dominate the conversation. Create pauses where she can make a comment or just an affirmation like "Yeah," or “Okay.” Eventually she'll make lengthier contributions to the conversation.
Share something about yourself. It’s up to you how personal you want the topic to be. She’ll make a comment about what you said or reply to a question you threw in. She might even say something about herself.
Find something both of you can relate to. Talk about something that happened in a class you’re both in. If you work at the same place, mention something that happened on the job. You could also bring up a new addition to the menu at a restaurant you both frequent. This will give her an opportunity to chime in.
Don’t jump to an unrelated topic. If you’ve been talking about that hot new TV show on Netflix, don’t try to prevent silence by switching to your desire to upgrade your phone. Gracefully end the conversation if you can't think of something. You could say something like, "Well, I have to get going, but let’s meet up for lunch!"
Pay attention to eye contact. This might help you get a better understanding of how she feels around you. Try to make short periods of eye contact with her when you stumble upon a common interest or even dislike. As you get to know each other better, try to hold her gaze longer. Don’t worry if she doesn’t want to keep eye contact at first. She might prefer to glance at you, rather than locking eyes for the entire conversation.
Don’t lead her on. If you're not seeking a romantic relationship, make that very clear in the beginning. You don’t want her to remember you as the phony jerk who only pretended to like her. Avoid flirtatious behavior, such as putting your arm around her. Be friendly, but also make it clear you're interested in other people. This way, she'll at least know that you're not romantically interested in her without hurting her feelings.
Getting to Dating
Earn her trust. As a shy person, she might not trust you immediately. Over time, you’ll have to prove yourself. Keep all promises you make to her. If she makes a social faux pas, don’t blab it to your friends. You could also tell her something you’ve only shared with one or two other people. You’ll know you’re making progress when she starts sharing what’s important to her.
Let her know you like her. Tell her yourself, as opposed to having a friend tell her for you. Stay calm and relaxed. Profess your feelings naturally and casually. When there’s a lull in the conversation, say something like, “I really enjoy talking to you and being with you. Would you be interested in taking our friendship to the next level?” Don’t hide behind a phone or computer screen. Tell her in person. Break the news to her when you’re alone to prevent her from feeling embarrassed. Avoid complimenting her appearance in the beginning. She might think you're being sarcastic.
Ask her out when it feels right. Get to know her before you ask her out. When you do ask her out, work it into the conversation. Start talking about a new movie you want to see, an event happening over the weekend, or a local place you’ve been wanting to visit. Try questions like: “Speaking of that new Mediterranean restaurant, I’ve been meaning to go but never got the chance. How about going with me Friday night?” “That guy’s a riot! You know, I have an extra ticket to his stand-up act this weekend, if you’d like to come along.” EXPERT TIP Moshe Ratson, MFT, PCC Moshe Ratson, MFT, PCC Marriage & Family Therapist Moshe Ratson is the Executive Director of spiral2grow Marriage & Family Therapy, a coaching and therapy clinic in New York City. Moshe is an International Coach Federation accredited Professional Certified Coach (PCC). He received his MS in Marriage and Family Therapy from Iona College. Moshe is a clinical member of the American Association of Marriage and Family Therapy (AAMFT), and a member of the International Coach Federation (ICF). Moshe Ratson, MFT, PCC Moshe Ratson, MFT, PCC Marriage & Family Therapist Find common interests informally. Connecting based on common interests is engaging and fun, especially if done informally, like going out for lunch, a drink, or coffee. You can reduce the pressure of the shy person by planning activities for the first few times you hang out together.
Practice caution with physical contact. Start with slight actions. For example, you could touch her hand when she borrows your pencil. If she reacts positively, continue. If she doesn't, back off, at least for the time being. The worst thing you can do is try to pressure a shy person into something that makes them feel uncomfortable.
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