Southside with You (2016)

IMDb plot summary: Chronicles the summer 1989 afternoon when the future President of the United States of America, Barack Obama, wooed his future First Lady on an epic first date across Chicago's South Side.
Directed by Richard Tanne. Starring Tika Sumpter, Parker Sawyers, Vanessa Bell Calloway and Phillip Edward Van Lear.

(Spoilers ahead.)

There are only a few movies that attempt to do a love story in a day. Before Sunrise is the best of them. It's an ambitious attempt, as the relationship has to get to a deep enough level in a single day to keep the dramatic arc going and help us get to know the characters. Before Sunrise makes this happen by making the conversation primarily an intellectual one, with tidbits about personal lives slipping out now and then. Southside With You gets significantly more contrived, with characters volunteering information about themselves that they really have no reason to share except for being charmed by the other person -- but, you know what, the actors are both so likable that I mostly believe it. Like any good romantic comedy, it's easy to look past awkward plotting if the leads have chemistry, and that absolutely works here. For large sections of the movie, I completely forgot they were based on real-life people and just rode along with the characters as they were.

My one complaint, however, is with the ending. When Michelle confronts Barack about not accepting the boundaries she set at the beginning of the day and instead persistently pushing until she allowed it to be a date, against her better judgment, he doesn't acknowledge that at all. Instead, he does another small romantic gesture and apparently that magically fixes things. At no point is her biggest concern about the relationship addressed, even in a small way (seriously, it only would've taken a line), and that leaves a bad taste in my mouth, which is not how you want to leave a rom com. It's so close to being a really lovely film, and as such it's so disappointing that they couldn't tie up that loose end.

4 stars.

How it entered my Flickchart:
Southside With You > Days of Heaven
Southside With You > A Clockwork Orange
Southside With You < Kramer vs. Kramer
Southside With You < The Goodbye Girl (2004)
Southside With You < Bicentennial Man
Southside With You > Catfish
Southside With You > GoodFellas
Southside With You < Shall We Dance? (1996)
Southside With You > Cats and Dogs
Southside With You > Spellbound (2002)

Final spot: #558 out of 2499.