An event which is made sadder by a later event. Differs from
Harsher in Hindsight in that the events may not necessarily be bad or harsh. The events that are
Heartbreaking In Hindsight might be a
Heartwarming Moment and it is only until the later event that you see sadder subtext in the first one.
Compare
Harsher in Hindsight,
Heartwarming In Hindsight,
Tear Jerker. Contrast
Hilarious in Hindsight.