Check Out Drew's Old Flame was the 16th episode of The Drew Carey Show, also the 38th overall episode in the series. Originally aired on February 19, 1997 on ABC, This episode, which was directed by Gerry Cohen, was written by Susan Dickes.
Drew's down payment on a car bounces because of a bad check at a garage sale. He finds out the woman who wrote the check was Kyra, his girlfriend from junior high school. She claims her roommate wrote checks from her account to cover his gambling debt. Drew invites Kyra to stay with him but begins to doubt her when his car is repossessed after her second check also bounces.
Drew buys a new car, but learns that the check for the down payment has bounced. A woman wrote a bad check at Drew's garage sale. Drew meets with her at the Warsaw to get his money. He finds that she is Kyra Sullivan (Ann Manguson), his old girlfriend from junior high school. She apologizes and claims that her roommate wrote bad checks from her account. After she reports that her roommate's gambling debtors might be after her, Drew invites her to stay at his house. He later asks her on a date. Drew's car is repossessed after Kyra's second check also bounces. When Drew confronts her, her roommate, Mac (Daryl Drummond) shows up and threatens them. He gives Drew the money that Kyra owes him. Drew feels bad about doubting Kyra, and then promptly sleeps with her. He awakens in the morning to discover that she has stolen all of his furniture, save his television set!
Turns out that Kyra was scamming him all along, and is not at all the girl that he once knew from junior high, as he first laments "that he's slept with a stranger", then after thinking for a bit, smiles proudly and boasts "Hey, I've slept with a complete stranger!". Drew looks forward to receiving a substantial insurance payment as he and the guys sit with him in his now completely empty house (execept for the old TV set), but then, as Kate stops by to tell the guys that she consolidated all her debts into a one big loan 21% - no payments for a year, as Drew sarcastically says she joined "The Idiots Club"!
Then a state trooper (Daryl Keith Roach) stops by to inform Drew that they found his stolen possesions, as Kyra and Mac, who turned out be her brother, who was also in on the scam, crashed his truck as they got stopped and arrested, as he also got a small reward for $50.