Double Whammy Friday is an unofficial internet observance that occurs when two unofficial holidays align together.

1) Free Use Friday (falls 11th to 14th of October) depending on year

2) 14th of October

When Free Use Friday happens to fall on the 14th of October (this happens roughly every couple years or so) then two things are fair game.

1) A couple must engage in sex whenever even just one member asks for Sex

2) you text your crush you like them, and if they like you back you must go on a date with them.

Both of these are allowed on Double Whammy Friday. However because of how the calendar works, the day alignment falls only every 5 years or so and thus it does not occur every year.
Friend 1: Bro, apparently this year there is going to be a Double Whammy Friday, because the calendar checks out

Friend 2: Yo bro nice, you should ask your crush out then.
by davidmilldurger April 1, 2023
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