How do I help my shy 2nd grader make new friends?

I’m sorry but you absolutely have to host more play dates, stop judging the other parents, get to know them in depth, quit making small talk, and MODEL building friendships with a diverse group of people. This is the only way, and you need to work at it for the next 12 years. Sending him to an after school program or camp will not work and will certainly not work with the peer group he’s spending time with for the next few years, his classmates. Volunteer to help with school related projects - get involved and get to genuinely know people. He is modeling your own anxious, low self esteem, judgy behavior right now, and it will hurt him all his life. Invite the nicest family to dinner and make it a special evening. Then do it for the second nicest, and so on. Give your son (and yourself) the gift of being truly friends with a broad spectrum of folks - what an amazing gift for all of you.

Playdates are really the best.  At this age, you can do drop-off playdates so you don't have to deal with the parents.  I have a first grader and usually drop off at someone's house or have a kid dropped off in mine.  Figure out which kids have personality that will match well with your son and arrange playdates for the kids.  I found out that I cannot control who my kids play with in school but can encourage closer friendships with the kids I like by doing frequent playdates with them.  I found that if I invite a kid for drop off playdate and offer to host the answer is almost always yes since the other parents are getting kid-free time or one less kid to worry about the an afternoon, etc and my son loves to have playmates his own age (he has younger siblings but loves playing with kids his age or older).   I usually monitor the playdate but don't get involved to see which boys are good influence on my boy and they are a good fit and invite those over more often.  After school activities rarely help unless they are large groups or you do activities afterwards in smaller groups since the focus is on the class activities and the groups at this age are large enough that no friendships are formed during the class. 

You might consider reaching out to his teacher and ask their help to make a good friend match. Also, try new activities and he might meet like minded friends there. Good luck!

While playdates seem ideal, they may not be with this cohort of kids.  If you have nothing in common with the parents, why would your son feel comfortable with their kids? You could try extracurricular interests...sports, arts, etc. and see if your son finds his way through a common interest. 

Good Luck!

I have a first grade boy. I have observed that girls make friends by having good social skills while boys make friends by sharing common interests. This is of course a generalization but it might help your boy find some friends. See what he is interested in that other second grade boys are also interested in. Cultivate those interests. For example I gave my first grader a pack of Pokémon cards and next thing you know he is running with a pack of other Pokémon card collectors that he never played with before. If your son likes sports enroll him in team sports (individual sports like golf are not as useful in this scenario). Good luck! 

I have a more reserved son as well. I find it fascinating that our culture says being shy at age 7 is now an "issue" and poor well meaning parents (guilty myself at times) are made to believe we need to fix the problem. Honestly IMHO, I find that the vast majority of kids are just basically not very nice, because they are not taught to be so -this culture sees kindness as a weakness. I have always encouraged my kids to play with the kids they see by themselves/alone, to include them. Increasingly, excluding is what moves you up the social ladder. I would encourage your son to take up a game or activity at recess that is important and fun to him, and if others would like to join, great, and if not that's ok too.  Maybe you could talk to him about talking to his current group about it not being kind to exclude? We should train our children to be leaders, not followers. If you'd like him to have more positive contact then maybe scouting or sports or an outside activity where he can connect with kids who share his interest will help. It's not critical that he's best friends with his classmates, when he's in college he's not going to remember who he played with in 2nd grade but I'll bet you anything he'll remember the summer days you spent doing something amazing with him or the fun vacation your family had - He's only in 2nd grade, as long as he knows his family loves him he will be fine and as he grows more into himself he will become more comfortable - you are doing great!!

Keep hosting playdates with kids your son likes. At this age you can tell other parents they can drop off and pick up their kids. I think social development is crucial and kids need unstructured time to relate to their peers so I made it a priority to host even if it was not reciprocated or I didn't love the other parents. My daughter is a teen and she has a great friend since kindergarten and it is 80-20 we host the girls. She had another friend all through elementary school and we didn't really mesh with the parents but the kids friendship was important to them so we found ways to get along. It may not be a very efficient way to socialize your child but it's worth doing. As a teacher, I've met students who don't have playdates or get unstructured social time and they strike me as lonely. I wonder how they will relate to people when they are adults? Anyway provide those opportunities without pressuring yourself to do perfectly.