Add me to the list of those who think of him as creepy. Colin Hanks did the role very well. The creepiness isn't over-the-top, but many of us sense it. (Didn't he audition for Pete Campbell initially?) Creepy in what way, I can't firmly say. I can't quite put my finger on his intentions. Maybe it's my lack of knowledge with the way it was back then before Vatican II--my parents are Bobby Draper's age--but if any parish priest kept needling me in such a way, I'd not have been as polite as Peggy. (Of course, I'm already a cynical, "liberal" Gen Y-er who grapples with religion anyhow. I'm only mentioning it at all to offer perspective of how unsettling Father Gill's behavior was to me, as a Catholic.)
Father Gill kept inappropriately pushing and pushing at Peggy, and I have always wondered if it was a guise. I have thought that if Peggy was receptive to him, and if he felt he "saved" her, the relationship would have progressed to something romantic... at least in Father Gill's hopes. (Certainly not where Peggy was going.) it almost seemed like manipulation to fix the "lost girl" and then go from there.
I think perhaps Father Gill didn't acknowledge it himself, but he seemed pulled toward her in more than a zealous way. Maybe I read too much into the looks he gave her and him pleading to her expertise when asking her tor help for his Palm Sunday sermon (in his car, no less) and then free help for that dance. He got far too personal with her in matters beyond Catechism, and even trying to push her to "open up to him" was creepy to me.
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