5. Leslie Shay and Clarice Carthage
Leslie Shay (Lauren German) dealt with one tough situation after the other during the first couple seasons of Chicago Fire. It seemed as though things would improve when she started dating Clarice Carthage (Shiri Appleby), but the fact that the latter was pregnant with her ex-husband's baby made things, shall we say: complicated.
The relationship between Shay and Carthage was defined by the former being strung along by Carthage, who wound up moving out of Chicago and getting back together with her spouse. It seemed like it was always going that way, so watching Shay get hurt was not especially fun.