Historical clue formulations

• One footing the bill — 2025-05-23
• Single-___ — 2021-05-14
• Single-___ — 2019-08-09
• One taking care of the bill — 2019-04-18
• One putting money on the table — 2018-08-15
• Single-___ (like a certain health care system) — 2017-11-26
• Tab picker-upper — 2011-01-18
• Check writer — 2009-01-25
• One with checks and balances? — 2007-10-04
• Reimburser — 2004-05-25
• Debt clearer — 2003-04-05
• Restaurant dinner host, usually — 2002-06-14
• Check presenter — 2001-12-26
• Check writer — 1998-06-23
• Check writer — 1994-12-11
• Check writer — 1994-01-31