Do
Do approach the shy introvert subtly and by yourself. This is far more effective than in a mob of people where the shy person is socially overwhelmed. Ask them whether it is a good time to have a conversation. Asking for permission and creating space is helpful instead of just ambushing them on a day when they are in a bad place and not receptive to something.
Do speak quietly and gently. This is more attractive, soothing and encouraging to the shy mind than loud, frenzied voices.
Do find and talk about shared interests or problems. Introverts bond with others through intimate, personal or meaningful conversation.
Do most of the talking (but not too much). Shy introverts can take a while to warm up to you. Expect about 2–3 weeks.
Do keep your conversations and social encounters short and sweet. Introverts need time to absorb you and your words, and their shy element causes them to cautiously evaluate you. Let them process you slowly. If you're too outgoing and charismatic, the introvert might shrink into the background during your conversation.
Do make minimal eye contact. Too much eye contact is seen to initiate the fear centers in the brain and the fight-or-flight response. It's intimidating. The less you eye them like food, the more likely they'll speak openly.
Do let your conversations come naturally. Let them be spontaneous and don't ever plan them. The shy introvert, ever aware, will wonder why you're paying them so much attention, feeling suspicious, anxious and even paranoid of you.
Don't
Don't single them out in front of a group of people (such as your cafeteria group) to talk to. This embarrasses them.
Don't talk loudly and incessantly. This is overwhelming and embarrassing for them.
Don't make small talk about inane topics. Introverts generally dislike small talk. Talking about something irrelevant will both bore them and pressure them to talk.
Don't treat shyness like a disease or affliction. Don't pity them. They will sense it, and immediately withdraw from you with distaste.
Don't expect them to contribute as much as you do to the conversation.
Don't immediately extend social invitations to them, such as inviting them to your house, group, or party. This places too much social pressure on them.
Don't follow them around. This is irritating and anxiety-provoking.
Don't talk to them in a group or with another person. Too many people mean too much social pressure.
Don't make too much eye contact with them. This is perceived as being intimidating and too dominating and scary for the shy person to deal with.
Don't look contrived in your efforts to strike up conversation. Let it be natural and flowing. Shy people hate awkwardness just as much and even more than you do.
Don't be otherwise intense or overwhelming in any way, shape or form. Shy introverts are sensitive and become mentally drained easily.
Don't force, pressure or encourage them to do anything out of their obvious comfort zone. This will quickly cause them to lose their trust in you and retreat.
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