Season 5, Episode 17: Fear of Flying (1996)
Mark’s new hobby is building model airplanes. But after Tim takes him to an air museum, Mark gets interested in taking flying lessons. Jill is a hard no on this, arguing that it’s far too dangerous. After some conflicts with Tim - and a visit from some astronauts on Tool Time - Jill talks to Wilson and realizes that her fears of Mark flying are rooted in the fear her mother felt whenever her father would fly from one military base to another for work. Wilson takes the whole family up in his plane so Mark can try his hand at flying, and Jill finally agrees to let him take lessons.
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