According to Jim Season 8 Episode 9 - Kyle's Crush

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8 - 9: Kyle's Crush

Jim prepares Kyle for his first "date" with Ruby's slightly older piano teacher, Mandy, whom Andy has fallen for and is secretly dating behind Kyle's back.

Air Date: 2009-04-21

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VidSrc	WatchSeries	9 months
primevid		thehww	9 months

According to Jim: Season 8, Episode 9

8 - 9: Kyle's Crush