The episode starts on a beautiful summers evening on the Island of Sodor, where the Fat Controller is preparing for his date with Lady Whitingskrawl. The Fat Controller instructs Gordon to escort them to the Tidmouth Cigar Club, and tells James and Thomas to take some schoolchildren on a school trip, as their bus broke down and they have been looking forward to the trip for years. Thomas screams in response. The Fat Controller and Lady Whitingskrawl arrive at the cigar club, and the Fat Controller instructs Gordon to remain there and not cause any trouble. Gordon shouts at the Fat Controller in response. The Fat Controller and Lady Whitingskrawl enter the cigar club and take a seat at a table, taking their orders. The Fat Controller orders a pint of bitter for him, and a drink for Lady Whitingskrawl. The Fat Controller compliments Lady Whitingskrawl on her dress. Lady Whitingskrawl thanks the Fat Controller, and tells him that the dress belonged to her late husband.
- The episode is unfinished, as Andywilson92's hard drive stopped working when the episode was nearly finished. This is explained in What happened to Thomas and Freinds 4?, however, it is likely that another YouTuber might finish the episode.