When you feel comfortable enough around somebody that you would feel comfortable taking your/their condom (penis "hat") off during intercourse, as opposed to a circumstantial sexual encounter.
Jason: "I've been thinking... maybe it's time for hats off?"
Monica: "Yeah, you're clean, but your pull-out game better be on point!"
A Shackteau is a humble, weather-beaten, structurally questionable shelter located in a spectacular or highly coveted place—Wales, Jackson Hole, Sun Valley, Crested Butte, coastal Maine, the Alps—where the building itself may be worth almost nothing, but the dirt, view, access, and mythology make it absurdly valuable.
In use:
Shackteâu - We thought it was an abandoned shed until the realtor called it a rare alpine Shackteâu with unobstructed views and listed it for $2million.