When Jack's ex wife returns her engagement ring (a Gallo family heirloom), Elliot is inspired to propose to Maya.Finch goes to great lengths to assist Elliot in making everything perfect but the cancellation of Nina Van Horn day throws a spanner in the works.

When Elliot discovers that Maya has a date for the Blush Charity Auction, he asks Nina to set him up with someone to help make her jealous. So Nina sets him up with a doctor but when she can't make it, she hires an escort instead.