3 Favorite Dating Movies

Dating always seems to make good movie fodder, though most stray far from reality. Here are a few favorites that were bouncing around my head this morning:

40 Year Old Virgin seems to have it all: bad advice, the bar scene, and a send up of Speed Dating. (Some of the best speed dating bits are actually in the extras.) Way too many good lines to quote, as IMDB’s list goes to show.

Nice Guys Sleep Alone is lesser known, but twists the romantic comedy to shows what happens when a too-nice Southern teacher stops being nice. The best quote from this one is easy:

Friend: You should totally hit that.
Carter: She’s my sister!
Friend: By marriage! In Kentucky they’ll arrest you for playing rap music before they arrest you for sleeping with your sister.

Other bonuses: unintentional sex ed for his class at the horse ranch, and a Netflix connection.

40 Days and 40 Nights starts off as a romantic comedy with Josh Hartnett being a guy whose life is being ruined by all the women that fall into bed with him, so he decides to completely abstain. From there it quickly turns into a cruder movie and more entertaining movie as his guy friends start a betting pool and all the women in his life try to regain the power they’ve lost. It sets the tone that the first line to come to mind is Horatio Sanz’s (of Saturday Night Live Fame) reply to his suddenly masturbation-crazed boss having done it three times before lunch: “Two more and you break my company record!”

Kevin Smith gets two honorable mentions for the following two lines:

  • “Did you love every woman you slept with?” “No, some of them I downright despised.” - Chasing Amy
  • “You know how when you spoon with someone and you can’t find a comfortable place to put that other arm? That was like a metaphor for our whole relationship.” - Mallrats
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