Bob is genuinely happy for Red and Kitty to be able to spend so much time with their granddaughter Leia over the summer of 1995, but he's also jealous that he doesn't get to see her nearly as much. In order to compensate for this change in their family dynamic, Bob tries to even the playing field by spoiling Leia with gifts for her birthday – though to quite disastrous results. He buys her an expensive karaoke machine and decides to serenade her dressed as Tom Jones, but hits the wrong song in That '90s Show and ends up singing Boyz II Men's "I'll Make Love to You.

After seeing the expensive karaoke machine that Bob bought her, Red decided to scrap his birthday gift of a cordless drill and give Leia an even better birthday present: Eric's old Vista Cruiser. While it may have been sitting in the garage for the past 15 years, being gifted a car is an incredible gift for a teenager, which is hard for Bob's karaoke machine to beat. At the end of Leia's 15th birthday celebration in That '90s Show season 1, Bob is defeated and tragically feels like the inferior grandparent.