Pronunciation: [skwˈe͡əɹ ˈʌp] (IPA) 
The phrase "square up" is pronounced /skwɛr ʌp/ and its spelling may appear unconventional. The "sq" beginning of "square" is an example of the rare consonant cluster in English, and the "u" in "up" can easily be mistaken for an "e" in terms of spelling. However, the unique spelling of "square up" helps convey its distinctive meaning of settling a debt or dispute, and has become a recognizable phrase in contemporary language.
Square up is a phrasal verb with multiple meanings, used both in a literal and figurative sense. In its literal sense, square up refers to the act of positioning or aligning something so that its edges or sides form a perfect square shape, or to make adjustments to ensure that something is level, straight, or even.
In a figurative sense, square up has different connotations depending on the context in which it is used. It can mean to settle a debt, bill, or financial obligation, especially in a fair and honest manner. It implies the act of resolving or reconciling financial matters in order to achieve balance or make things right.
Furthermore, square up can also refer to preparing oneself mentally or emotionally to face a challenge, conflict, or confrontation. It suggests the idea of bracing oneself or gathering courage to confront and deal with a difficult situation head-on.
Additionally, square up can be used to describe the act of preparing oneself physically, such as getting ready for a competition or a fight. It denotes the process of adopting a proper stance or posture before engaging in a physical activity.
Overall, square up can encompass various meanings related to aligning, settling, and preparing oneself, both in a literal and figurative sense.
The phrase "square up" has its origins in 19th-century slang. The word "square" was commonly used during that time to indicate fairness, honesty, and straightforwardness. It referred to someone who was honest in their dealings and actions. This usage of "square" eventually led to the phrase "square up", which means to settle a debt or dispute in a fair and honest manner. Over time, "square up" also came to mean preparing or getting ready for an upcoming challenge or confrontation, likely due to the association of fairness and directness with readiness.
