A tale of double standards and alliterative first names, How to Lose a Guy in Ten Days could also be described as a guide for How To Not Be Like Those “Other” Women. Though deeply steeped in the early-aughts culture [body shaming! gender essentialism! workplace harassment!] this movie is still a banger. While maybe not his highest-brow œuvre, Matty McCoogenie™ still reigns as McKenzie’s dreamboat himbo in this rip-off of 1964 movie Sex & the Single Girl.

Of all movies to compare this to, McKenzie did not expect for Bob to find so many parallels to Tommy Wiseau’s The Room. Under close scrutiny, this film is actually nuts: packed with weirdos, weird accents, and weird pacing. McKenzie has to admit that this one hits different (worse) on the 30th watch, but her primary takeaway is still the same: Italy looks sunny and Diane Lane looks hot hot hot in an hourglass dress.

It only feels right to kick things off with the rom-com that gave Baby Fish Mouth its name. A cornerstone of the genre and one of its most enduring touchstones, McKenzie suspected she might make a quick convert out of Bob with When Harry Met Sally. Little did she know that he’d spend most of the movie lusting after Amanda Rice - Reese - I can’t believe you don’t remember her name.