Squeeze somebody dry Definition 1 of 1Pro Tip 1/3Metaphorical Use The phrase is used figuratively and does not involve actual squeezing or drying. The constant demands from the charity squeezed me dry. Pro Tip 2/3Negative Connotation Implies exploitation or taking advantage unfairly. The loan sharks squeezed the businessman dry with high interest rates. Pro Tip 3/3Emotional Impact Used to express a strong emotional response to being overused or exploited. Working two jobs to pay the bills has completely squeezed me dry.