He's gotta be older than Gary....he likely did NOT need a chaperone for that New York trip, and indeed, I can't see Alana bringing Gary over to the house as a "date" -- papa would not approve.
Interesting: there is no scene about it, but evidently papa (and mama) DID approve Alana travelling to New York as the chaperone for a "15 year old boy." She probably made Gary sound like a LITTLE boy, a child actor. Alana ended up with a pretty glamourous trip out of that -- BECAUSE of Gary.
And yet she betrayed Gary and got with Lance. But it didn't work out.
PS. Part of the "precision" of this Oscar-nominated script. On the plane to New York, "child actor" Gary actually draws the flirtatious attention of the flight attendant, who recognizes him as an actor and "comes on to him" a bit -- women will soon be VERY easy for Gary to get. Alana notices this, and shows off her first jealousy in the film.
But then Lance comes back -- older and from first class -- and the jealous Alana switches her attention to him. And now Gary gets to be the jealous one.
A lot of sexual tension up in that plane.
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