Michael Sicinski’s review published on Letterboxd:
An utter delight. A film that probably shouldn't work. It's all over the place yet disciplined. It projects a sense of cool indifference about its characters and its plotlines until you realize that everything was worked through to the very end, and everyone depicted in the film was shaped with great affection. You think all the stories are going to intersect. You worry. Then you suspect that none of the stories will actually intersect. You're relieved, even if that leads to a feeling of hip detachment. Then the kicker. Two stories briefly intersect, and two do not. A solution you never saw coming.
The title of Person to Person describes director Dustin Guy Defa's fundamental method of building the film, moving through the city and across time not so much according to narrative logic but as individuals encounter one another, and their competing motivations and wholly incompatible worlds bounce off each other. (This is a film that exhibits the timing of a farce, and yet its structure is one that might well have been generated through improv exercises.)
But "person to person" is also an old-fashioned type of operator-assisted telephone call. If you didn't reach the specific person you were calling, you were not charged. In light of this, I think about the film's relationships in terms of determination and intent versus a willingness to take what you get in life. You encounter people along the way, but are they the specific ones you need?
If there is one possible constant in Person to Person, it's that the longer you are alive, the more secure you become in who you are. Someone like Jimmy (Philip Baker Hall), the watch repair shop owner, is not going to do anything he doesn't want to, whereas Claire (Abbi Jacobson) entreats him to help her out and give her a scoop regarding a possible murder case, so she can figure out if she even wants to be a reporter. Likewise, Phil (Michael Cera) wants to motivate Claire to be successful because he's attracted to her, but also because that would mean he is a good mentor, something he needs to believe about himself.
Then you have the two roommates. Bene (Bene Coopersmith), a jazz nerd, is excited to have found a guy selling a rare Charlie Parker LP. But when he finds out it's a fake, he chases the crook halfway across town in a mid-speed bicycle chase. (The two men's pause to walk their bikes down subway platform stairs is priceless.) Meanwhile, his buddy Ray (George Sample III) is on the run from his ex-girlfriend's brother for an untoward post-breakup maneuver. While Defa doesn't make too much of it, Bene and Ray are a clear contrast where integrity is concerned.
Finally, the two young women, Melanie (Olivia Luccardi) and Wendy (Tavi Gevinson), are a comic interrogation of the problem of loyalty between girlfriends when one becomes involved in a relationship. Defa plays his hand rather broadly here, but to strong comic effect. Melanie is seeing the blandest dude imaginable; she actually becomes duller in his presence. Meanwhile, it is painfully obvious that the bitter, sardonic Wendy is in love with Melanie. (Her queerness is confirmed in the course of the film.) But, out of a desire to challenge her comfort zone, she hooks up with the tagalong best friend (Ben Rosenfield). It goes nowhere, but it's more of a risk than anyone else is taking.
Simply by lining up all of these pairs and quartets, contrasts and dualities, I am in jeopardy of taking Person to Person more seriously than it takes itself. Yes, it is structurally sound, bearing a surface resemblance to certain more serious cinema -- Woody Allen, perhaps, or Noah Baumbach. But Defa's film is fleet of foot, light as a soufflé, and skronky like free jazz.