(verb): To deride someone verbally about fundamental aspects of the person's life. Generally, the derision is done by a baby boomer towards a younger person, normally generation y. The term was used extensively in David Foster Wallace's posthumously published novel "The Pale King." Squeezing someone's shoes goes beyond good nature ribbing or teasing because it isolates more serious qualities in the person whose shoes are being squeezed (i.e. career, or other serious existential questions).
Damn, Dad is really going to squeeze your shoes about dropping out of college and your general mid 20's malaise.
by headstash_mcgee July 17, 2014