Pictures from the end of 2008 and new ones from this new year.

The Maguire family hang out with Kevin Connolly.

Sources: Popsugar and

Tobey, Jennifer and Ruby out and about.

Sources: Popsugar, Posh24 and CelebrityBabyScoop

The Maguire family hung out with friends Sara Gilbert & her kids and with Ethan Suplee & his family.

Sources:, Celebs&Bubs, Posh24 and CelebrityBabyScoop

The Maguire family did some more hanging out together.

Sources: CelebrityBabyScoop and JustJared

Tobey and Ruby shared some father-daughter time together.

Sources: Popsugar,, CelebrityBabyScoop, Posh24 and Socialite’s Life

The Maguire family looks adorable in shades.

Source: CelebrityBabyScoop

Tobey and Jennifer did a quick shop stop with Ruby.

Source: StarzLife

Tobey hung out with his girls and a friend.

Source: Teddy&Moo

Leonardo DiCaprio and Kevin Connolly hung out with Tobey and his girls in December. Ruby looks so cute with uncle Leo.

Source: and Popsugar

Tobey, Jennifer and Ruby spent the New Year in Cabo with some very famous friends. Leonardo DiCaprio, Kevin Connolly and Lukas Haas were there with the Cox-Arquette family and Jennifer Aniston, as well as Laura Dern and Sheryl Crow.

Source: Popsugar

Tobey saw the off-broadway hit show “Rock of Ages”. He was in good company. The actor Patrick Wilson joined him.
Tobey is rumoured to be producing the musical into a movie and there’s talk of Patrick to be on the wish-list to star in the movie.