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To be or remain in an ideal situation or advantageous position. I think it's pretty disgusting that your company sat pretty while millions of people lost their homes as a result of your negligence. Despite the protests in the country's streets, the despotic regime will continue to sit pretty unless an international intervention is mounted. With all the money you inherited from Aunt Myrtle, you'll be sitting pretty for the rest of your life.
In an ideal living situation (typically because one is financially comfortable) or advantageous position. With all the money you inherited from Aunt Myrtle, you'll be sitting pretty for the rest of your life. I'll be sitting pretty for the rest of the semester if I can ace this test.
living in comfort or luxury; living in a good situation. (*Typically: be ~; leave someone ~.) My uncle died and left enough money for me to be sitting pretty for the rest of my life. Now that I have a good-paying job, I'm sitting pretty.
In an advantageous position; also, financially well off. For example, The terms of the will left Mary sitting pretty. Although the use of pretty in the sense of "advantageous" is much older, this colloquialism dates only from the early 1900s. It was given extra currency as the title of two different musicals, Sittin' Pretty (M. Moore, 1921) and Sitting Pretty (G. Bolton and P.G. Wodehouse, 1924).
sitting prettyin an advantageous position or situation. informal
mod. doing very nicely; in a very pleasant and secure position. She married a millionaire, and now she’s sitting pretty.
In an advantageous position. This colloquial Americanism dates from the early l900s. A popular song of the period was “I’m Sitting Pretty in a Pretty Little City” (1923), by Lou Davis, Henry Santly, and Abel Baer.