When the flashback takes place, 15 years earlier, Ray and Debra watch a Blockbuster movie. Blockbuster did not open until 1994. This episode aired in 2002 and takes place 15 years earlier in 1987.
Father Hubley says he has known the Barone family, and is introduced to Debra, during the period when Ray & Debra first started dating. But in The Wedding: Part 2 (1998), Debra introduces Father Hubley to Ray for the first time, when they go to get premarital counseling from him. How could this be possible?