For Love Or Money [1963]

In this romantic comedy, Deke Gentry (Kirk Douglas) is a lawyer who gets an unusual assignment from Chloe Brasher (Thelma Ritter), a wealthy widow, owner of a successful hotel chain, and one of his most prominent clients. Chloe has three daughters, sensible Kate (Mitzi Gaynor), bohemian Jan (Leslie Parrish), and heath food fanatic Bonnie (Julie Newmar), and she wants Deke to find them husbands. Though Deke protests that matchmaking is outside his traditional area of expertise, Chloe is insistent, and he ends up taking the job. To be sure that he's going through with it, Chloe assigns her security chief Joe (William Bendix) to keep his eye on Deke. Eventually, Deke fixes up Bonnie with Harvey Wofford (Richard Sargent), a meek IRS agent, and pairs Jan with artist Sam Travis (William Windom), but Kate turns out to be the hardest Brasher sister to marry off, until he throws his own hat into the ring.