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The Five Most Awkward Movie Dates Ever

  • Kempt Staff


Don’t let the greeting card industry fool you—no matter how well-phrased a few rhyming couplets might be, Valentine’s Day is just like any other day.

Which means your date tomorrow night could go any number of ways, including downhill. Or at least into an awkward spiral from which it may or may not recover. It happens to the best of us. So, partly in celebration and partly as a cautionary tale, we present to you:

The five most awkward movie dates in cinematic history...

The Movie: When Harry Met Sally. The Setup: A double date. That Awkward Moment: When the two who weren’t even paired together on the date miraculously hit it off while Harry and Sally are left to exchange furtive glances across the table in silence.

The Movie: Goodfellas. The Setup: A second-chance date after one already horrible one. That Awkward Moment:Henry stands up Karen on the second date, so she tracks him down at his hangout to embarrass him in front of everyone by making a scene.

The Movie: Hitch. The Setup: The excursion date on jet-skis. That Awkward Moment: When Hitch attempts to mount Sarah’s jet-ski after his breaks down, he full-on high-kicks her in the face.

The Movie: Clueless. The Setup: A late-night movie date. That Awkward Moment: When Cher invites Christian over with the intention of bedding him and fully personifies the movie title by not getting the hint that she’s barking up the wrong tree.

The Movie: American Psycho. The Setup: An impromptu after-work dinner. That Awkward Moment: When Bateman pulls out the nail gun.