Historical clue formulations

• Regretful soul — 2022-09-13
• Regretful one — 2015-06-02
• One with misgivings — 2015-01-26
• Regretful one — 2013-12-09
• Sorry sort — 2013-06-05
• Regretful type — 2009-09-23
• Monday morning quarterback, maybe — 2009-04-17
• Penitent — 2009-01-16
• Sorry sort — 2008-04-20
• Regretful one — 2006-12-27
• One who's sadder and maybe wiser — 2006-06-07
• One having second thoughts — 2005-10-23
• One kicking oneself — 2005-10-19
• One who's sorry — 2005-09-29
• Who's sorry now? — 2005-06-24
• One having second thoughts — 2005-01-02
• One with second thoughts, say — 2003-08-20
• Sorry soul — 2003-07-25
• Sorry sort — 2002-02-09
• Remorseful one — 2002-01-13
• Sorry sort — 2001-12-20
• Person kicking himself, maybe — 2001-05-12
• "Shoulda, woulda, coulda" thinker — 2000-03-12
• Wistful sort — 2000-01-27
• Remorseful one — 1998-07-08
• Penitent one — 1996-11-14
• Regretful one — 1996-04-27
• Sorry soul — 1995-11-12