For some kids, starting conversations with strangers and making new friends is easy and fun. For other kids, "fitting in" is a difficult, uncomfortable, and painful process associated with a lot of fear and worry rather than excitement. In addition to emotional support, shy or socially awkward kids often need help learning social skills in order that they can become more capable of creating and then maintaining friendships.
Parents can help children learn social skills in a few different ways. First, caregivers can offer to help children brainstorm ideas about how to start new conversations or join into games. Shy children are sometimes so anxious that they can't easily think through the mechanical process of what they need to do to walk up and introduce themselves. Their anxiety interferes with their ability to think clearly. Offering children concrete suggestions for what they can do and say in novel social situations helps them to focus and gives them a plan of attack.
For example, some kids feel like they can't think of anything to say when they meet new people and will instead stand around feeling and looking awkward. Kids who learn and use a couple of standard "fall back" questions, such as "Whose class are you in?" or "Do you like to play basketball?" will likely feel more prepared and comfortable meeting other children.
Knowing things to do and say is not the same thing as feeling comfortable doing and saying them. Role playing can help children to practice their new skills so as to give them a feeling of comfort when putting preconceived plans or topics into action. Children and caregivers can take turns playing different roles (e.g., one can play the "new kid" while the other plays the "shy kid") and trying out various responses and actions. Keeping a sense of humor while engaging in such role plays can help make the practice seem fun rather than punitive or forced. Though it is not actually the real situation, role playing forces children to confront their social anxiety in a very real way, and so it is useful for parents to keep in mind that the process may leave children feeling anxious. This is not a bad thing, as the only way for children to get over their social anxiety is to feel it and work it through, but it is nevertheless an uncomfortable process.
Some children are able to make friends easily, but seem to have trouble maintaining friendships. Parents may need to observe their kids (as surreptitiously as possible) across several different situations in order to figure out what behaviors contribute to this problem. For example, one child may have trouble sharing; while another promises to keep secrets, forgets the promise or disregards it, and then shares private information in an unauthorized public manner. Similarly, children may display problems in that they don't listen to what their friends have to say, fail to communicate respect, are bossy, are chronically disagreeable or jealous. Through the process of behavioral observation, parents and caregivers can become aware of what children are doing wrong (e.g., what they are doing that is causing others to reject them) and raise children's awareness of this behavior as a problem which can be avoided by their learning to behave differently.
Parents who have become aware of a child's social skill deficit are in a precarious and delicate place. On the one hand, they are in a position to offer the child valuable constructive criticism which the child can use to improve his or her social life. On the other hand, what they have to offer is criticism (constructive or not, it matters little), and the typical response people of all ages have to criticism is to take it as an attack and get upset about it.