The Girl Most Likely (1958)

Dodie aspires to marry a wealthy man for a glamorous lifestyle, but her current boyfriend, Buzz, a struggling housing salesman, isn't the ticket. After accepting Buzz's proposal, she encounters Pete, whom she initially believes to be affluent, only to discover he’s merely a boat mechanic. Despite this, they enjoy a delightful date, leading to another proposal from Pete. Dodie's luck seems to change when she meets Neil Patterson, a genuinely rich man. Their lavish date on his yacht in Mexico culminates in another proposal, forcing Dodie to make a life-altering decision.