Date     | YESorNO
---------------------
01/01/2001 | NO
01/01/2002 | NO
01/01/2003 | YES
01/01/2004 | NO
01/01/2005 | NO
01/01/2006 | NO
01/01/2007 | YES
01/01/2008 | YES
01/01/2009 | YES

var query =
(
    from m in db.MyTable
    where m.Criteria == XYZ
    select new
    {
      Date = m.Date,
      YESorNO = m.YESorNO
    }
).OrderBy(x => x.Date);

var query =
(
    from m in db.MyTable
    where m.Criteria == XYZ
    select new
    {
      Date = m.Date,
      YESorNO = m.YESorNO
    }
).OrderByDescending(x => x.Date);

var result = query.AsEnumerable()
                  .TakeWhile(x => x.YESorNO == "YES")
                  .LastOrDefault();

var query = db.MyTable
    .Where(m.Criteria == XYZ)
    .Select(e => new { Date = e.Date, YESorNO = e.YESorNO })
    .OrderBy(e => x.Date);

var latestNODate = query.Where(ee => ee.YESorNO == "NO").Last().Date;
var element = query.Where(e => e.Date > latestNODate && e.YESorNO == "YES").FirstOrDefault();