Tonight is Jack’s first Halloween, and because it’s a Monday, he’ll actually be dressing up for the 3rd time this weekend.

On Saturday, Christine, Jack and I headed over to a neighbors house for their 2nd Annual Halloween Playgroup (yess, grown men go to playgroups too). Jack was too cute, as were the other kids in the neighborhood.

Jack was a “Jack in the box” this year, and he wore a costume that was completely handmade. Christine made the outfit on her sewing machine, and we painted the box in the backyard. The final touches to the outfit were added here and there (that means while Jack was napping) over the past week, with it all coming together on Friday night. The end result:

Christine did a great job, didn’t she?

We loaded our “Jack in the box” up in his little red wagon, and walked around the corner to the neighbor’s. Jack made it about 1/2 way before he had to come out of the box… he wasn’t digging it as much as we’d hoped.

At the playgroup, all of the kids played inside and outside, with parents hovering, talking, and taking photos. It was our first time to meet the hosts, and they were lots of fun. At the party, two of the five moms that were present were pregnant… must be something in the water.

See all of the photos from the playgroup here, those kids sure were cute. There’s nothing like seeing Superman testing the slide before going down it, or Piglet sitting at the foot of the slide. Here’s a princes in a swing, and another princess trying to get up on the hammock, a Jack sliding down the slide, and a hula girl sliding down too.

We came home around 5:30 and relaxed before our more adult party that started at 7:30.

Around 7:40, we headed over to Erin Taylor’s house for Carlo and Erin’s annual Halloween bash. We’ve attended this party two years in a row now, so we were excited about taking Jack this year. They toned it down a bit this year, but it was loads of fun…

Here’s a photo of the “Classic Toy Family”:

Baby Doll, Jack in the Box, and a Toy Soldier

See the rest of the photos from Carlo and Erin’s party here. And yes, Jack was the life of the party till Jack and I came home at 9:00 … after that, you’ll have to ask Christine, but I heard that it got pretty crazy.