In 2009’s He's Just Not That Into You, a romantic ensemble built on a bestselling advice book somehow wound up being about emotionally stunted men, red flag relationships, and one very confused Scarlett Johansson.

Truman and Landen dig through the all-star cast and pop feminism of this late-2000s relic to find out how a dating guide turned into two hours of mixed messages and bare-minimum boyfriends.

A glossy rom-com about mixed signals and missed connections, He's Just Not That Into You follows a group of Baltimore singles stumbling through love and heartbreak, loosely inspired by the self-help book of the same name. Directed by Ken Kwapis and starring Ben Affleck, Jennifer Aniston, Drew Barrymore, Ginnifer Goodwin, and a pre-Marvel Scarlett Johansson, the film was a Warner Bros. release during the late-2000s boom of ensemble romances. It made money, got lukewarm reviews, and quietly slipped into cable rerun oblivion—despite a cast list that reads like People Magazine’s Class of 2009.

What You’ll Hear:

• – The film’s confusing tonal mix of self-help cynicism and soft-focus sentiment
• – How Hollywood was trying (and failing) to bottle up modern dating anxiety
• – The bare-minimum bar for male behavior in late-aughts romantic comedies
• – A heated dissection of Justin Long’s hangout lair
• – Who this movie thought it was helping — and why it probably wasn’t

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Tags: He’s Just Not That Into You, 2009, Ken Kwapis, Aniston, Affleck, Barrymore, Goodwin, Johansson, romantic comedy, ensemble film, dating movies, 2000s rom-coms