On the first episode, Lainey was using either a late 80s/early to mid 90s model of a Macintosh. Also, Matt Ryan was born in 1985 making him a freshman in 1999. Apple came out with the iMacs and stuff in 1999 and that computer could probably have been well obsolete.

Watching the Singled Out episode and Singled Out ran from 1995-1998 and Lainey and CB went to see Babe only to find out it was sold out and instead they ended up seeingEyes Wide Shut which came out in 1999.