Crossing Delancey (1988) on Netflix

Thirty-three year old single Isabelle Grossman, who works at a small but prestigious Manhattan bookstore, is a modern, emancipated woman who doesn't need a career or a man to fulfill or define her as a person. If a man does enter her life, she will let it happen. Such is the case with "very separated" Anton Maes, a celebrated local writer whose outward bohemian attitude toward life she isn't sure is actually a come-on or just the way he is as a person with everyone. She would like it to be the former. To the contrary, being emancipated and modern is the reason that she rebels against the move by her Lower East Side grandmother - her "Bubbie" - to hire Hannah Mandelbaum, a matchmaker, to find a man for her. Who Hannah sets her up with is Sam Posner, a pickle maker and vendor. While Sam admits that he is attracted to Izzy and as such pursues her, she in turn can't see beyond the fact of he being a set-up and a pickle vendor truly to see him as a person for good or bad. When Izzy finally can see beyond those obstacles to find a cute, nice man she would like to get to know, it may be too late as Sam may be able to sense Izzy's apprehension to stick around for long. Izzy may also hedge her bets with Anton perhaps in the picture.