He's so shy

I'm sure it's not a shock to people who know me, but my kids can be very shy. It's not obvious at first since they're known for walking up to complete strangers and saying 'hi'--which isn't necessarily a good thing--or shoving one of their Thomas train engines or Matchbox cars in someone's face and screaming, "I HAVE A LITTLE THOMAS! I HAVE A GREEN DW BUS!" (DW is code for VW). But there are times, like when we're at the playground, that it takes a lot of urging for them to play beyond an arm length's distance from me, and it is nearly impossible to get them to play with other kids. I'm sure I'm partly to blame. If not for genetics, then for the lack of socialization. I couldn't put my kids in daycare because they were so premature and susceptible to sickness. And I didn't involve them in enough classes because...well, I have no excuse.

The other day, Drew really wanted a certain shovel in the sandbox. This shovel happened to be lying at the foot of a woman whose kid wasn't playing with it anymore. This is what happened next:

• Drew grabbed my hand and said to me, "Mommy, go get that shovel. I neeeeed it." 
• I said, "Drew, just ask the lady if she's using it. And if she isn't, ask her if you can have it."
• "No, Mommy, noooooo. YOUUUU do it. YOU get the shovel."
• I refused and told him if he didn't ask her himself, he would have to dig sand with his hands. (Okay, I admit, that was probably a little mean, but I really wanted him to be more assertive.)

I walked away to bring Henry to the swings. I looked back to see Drew say, "E'cuse me. Are you using that shovel? Can I have that shovel?" However, not only was he speaking slightly above a whisper, he was standing a full 10 feet away from the woman. Poor thing. He tried. I really think he did. Nevertheless, I kept my distance so Drew could build his confidence. But as soon as I saw the woman and her child leave the sandbox, I rushed over to Drew and told him to grab the shovel.

I think I'll hold off on Lesson Two of Assertiveness Training 101.