When Skippy falls head-over-heels in love with Mallory's new college friend, Amy Sussman, he's both startled and overjoyed to find himself in his first real romantic relationship. Just as Steven finishes an informal pep talk with the kids, unraveling his fool-proof plan to throw Elyse a surprise birthday party, Amy arrives to pick Mallory up for a study session. Skippy happens to drop by and is immediately taken with Mallory's shy and pretty friend. He's so smitten, in fact, he's rendered completely helpless, and Mallory ends up arranging their first date.