Season 7: Episode 153: Robert Needs Money
After deciding to lend Robert $1,000 when he complains he's struggling with finances, Ray and Debra are surprised when Robert uses the money for a vacation to Las Vegas. After Robert resists taking the money, because he's concerned he can't pay it back, Ray and Debra insist it's a gift. Later at Frank and Marie's, Ray and Debra are shocked when Robert announces he's going on vacation to Las Vegas. Ray and Debra question whether Robert has thought this through, but Robert says he needs a vacation and doesn't know when he'll ever have an "extra" thousand dollars hanging around again.