When a fully clothed person sits in a pie (or other cake like pastry) and commences to weep like a little girl. Squat Cobblering is usually engaged in by ugly, bald, middle aged men, who usually have some form of what appears to be mild autism. Said mild autism may manifest itself in an childlike, irrational and downright creepy obsession with baseball cards.
Did you see the back of his pants? He either crapped'em, or Hoboken Squat Cobbler'd a chocolate cake.
by Bob Barr 123 February 26, 2016
Hoboken squat cobbler is a sexual fetish act where a man or woman, fully clothed, slowly sits into a pie while singing a seductive song. The singing is what differentiates this from other pie-sitting fetishes, it is named after the hometown of Frank Sinatra, who is rumoured to have fathered the act during one of his famous drinking binges at a friends' birthday party. Frank Sinatra allegedly said at the time "Let me show you what we call the hoboken squat pie."
by SwampBeast February 23, 2016
Someone who takes videos of himself squatting naked on a pie, preferably of the cream type variety, and masturbating much to the delight of his intended viewer.
by Yankwood February 25, 2016
by Brad0419 April 03, 2024
by Brad0419 April 03, 2024
by Taylor MF Norrell September 07, 2015
basically part of new york and everyone thinks they're from the city. don't doubt them. the town is obsessed with frank sinatra and has the best city views
by sloths?? January 18, 2022