Shoestring (S01E02)

Tim is determined to win Cindy's heart, but his efforts repeatedly backfire, allowing Jim and David to sweep her away. As if humiliation wasn't enough, Tim finds himself inexplicably donning a dress, and to make matters worse, he can't locate his own pants. This unfortunate situation leads him to make his way home in a vibrant pink dress, further solidifying his status as the laughingstock of the group.