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Double-Whammy 

Verb (v.); Punching oneself in the testicals whilst cumming/having an orgasm.

Adjective (adj.); A way to describe someone that is sexually attractive but at the same time bad for you financially, personaly, etc.
When used as a verb: "I think I might double-whammy when I jack off today."
When used as an adjective: "Damn that hoe is a double-whammy!"

Double Whammy Friday

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.

Double Whammy Friday

Double whammy friday is an unofficial internet holiday / meme that began around 2015 or so.

It happens when two sub-holidays align on the same date, which only happens every several years, not every year. So when it does happen, its a big meme.

1) free use friday: happens 11 to 14 on the days of October, depending on year. it happens on the second friday of october

2) 14th of october

when these align, you have to do both challenges.

Manhattan Double Whammy 

Me and Al got a Double Whammy from that dude.

Which one?

A Manhattan Double Whammy.
Manhattan Double Whammy by AJJ304 October 29, 2008

Denny's Double Whammy 

Same as a double whammy, only it happens in a Denny's Bathroom
"my grand slam tasted terrible, now my friend and i are gonna denny's double whammy their ass"

New England Double Whammy 

When a penis gives out a double load of cum.
I gave that dude a Double Whammy.

Which one?

A New England Double Whammy.