It (1927 movie)
When Cyrus hosts a yachting excursion, Betty Lou makes Monty take her along, masquerading as "Miss Van Cortland". Cyrus at first wants to remove her from the ship, but he cannot long resist Betty Lou's it factor; he eventually corners her and proposes marriage, but she gets him back, by telling him that she'd "rather marry his office boy", which accomplishes her goal, but breaks her heart.