For Love or Money (1963)

Under threat of being sued by them, wealthy and controlling widowed dowager Chloe Brasher, a San Francisco-based hotelier, has uncharacteristically decided to hand over the control of her three adult daughters' trust to a third party from among a set list compiled by her, one of her new lawyers Deke Gentry of Martin, Barton, Tupper and Gentry to handle the transition. Being informed of the nature of the three young beautiful women who would trust no one their mother would suggest, Deke is able to get the three to agree to who they perceive as naive Deke himself being their new trustee, they unaware that he was on Chloe's shortlist. What Deke learns after doing so is that his primary initial task is to attend to a stipulation in Chloe's late husband's will that Chloe herself must approve of each of her daughters' respective spouse for them ultimately to receive their trust, of which none of the three are aware. Chloe, who wrote that stipulation herself, not only wants to approve their spouses, but wants Deke to arrange for the unions to the three men she has specifically chosen, each to balance out their lives, and, with the exception of one casual acquaintance from long ago, the men they don't even yet know. For youngest Bonnie Brasher, the fitness obsessed ditsy one, Chloe has chosen non-corruptible IRS investigator Harvey Wofford. For second Jan Brasher, the free spirit art loving hippie, Chloe has chosen prison administrator Sam Travis, the two who knew each other as children. Deke plans for each of these pairs to meet in the guise of a business arrangement which would blossom into love. While these two are difficult enough for Deke to arrange, the final one, eldest Kate Brasher, may the most difficult with she being the smart one as a motivational researcher. Wanting Kate to have some fun in life, Chloe has chosen wealthy womanizing Sonny Smith, president of the Smith Baby Food Company who happens to be Deke's best friend. Unlike Bonnie and Jan, Deke chooses a different tact in Kate arguably being more interested in meeting Sonny in a social setting in the guise of she wanting a business arrangement out of it. Complications ensue when Kate and Sonny even meeting is a difficult enough task in Sonny believing Kate probably not worth meeting if Deke doesn't want her for himself, and as Deke and Kate truly do fall for each other but can't admit it to the other under the circumstances.