As Seen In: Never Been Kissed (1999)
The Perp: Josie Geller (Drew Barrymore)

Men aren’t the only ones guilty of grand gestures in movies that would never translate well to real-life dating. In the 1999 chick flick Never Been Kissed, reporter Josie “Grossy” Geller takes bad romance to new heights by professing her love in the Chicago Sun Times to a teacher she deceived (by posing as a student).

But wait, there’s more. Following her big reveal, she pressures him to meet her on the school’s baseball field to demonstrate his acceptance of her apology by giving her her first-ever smooch in front of countless fans. PDA is one thing, but this just seems all kinds of wrong.

If we were in this dude’s shoes, we could probably get over the fake student thing, but a stunt like this would require years of groveling. Not to mention that a 25-year-old who's never kissed anyone most likely isn't someone you'd be thrilled about pecking in public.