Karen reconnects with her best friends after getting involved in a complicated relationship with a wealthy, married patient. The relationship went too far because she was having an affair with a terminally ill client to whom she had prescribed morphine. After his death, the man's son, Sam Grey, comes into her life, but he has no idea about her relationship with his deceased father.
In season two Karen works at an ER. She meets a patient called Anna Choi, who inspires her to go back into private practice. Anna makes up a story about being an escort. Karen finds this interesting and after reflecting on her loneliness while at dinner with April and Daniel, she decides to give it a try. She also reconnects with Jacob, who admitted to having had feelings for her. When she tries to build her social life back up, she decides to ask him out. He tells her he no longer has feelings for her. Jacob later reveals that he did still have feelings for her and they begin secretly dating. Jacob gets a fellowship in Boston and asks Karen to move with him. After thinking it over, Karen rejects his proposal. Karen then gets an unexpected guest, Ben who she'd slept with while experimenting with escorting. Ben tells her that he is HIV positive.
- Karen and Thomas Grey
Karen had an affair with Thomas Grey. They were in love, as she states in the deposition. She prescribed him with morphine, to release his suffering because he was terminally ill. They had a condo downtown, which Thomas allegedly used for late nights at the office, according to his wife Elisabeth.
- Karen and Sam Grey
Karen met Sam at the funeral of Thomas Grey, Sam's father. He grew an interest for the older woman, and started talking about the death of his father. He invited her to the condo of his father, where Karen had to pretend she didn't know the place. He claims they had a moment there, which Karen denies. A little while later they talk again, and they end up sleeping together. Sam says he'll be her alibi, but the next morning he testyfies in favor of his mother. He finds out about the affair between Karen and his father by accident, and Karen apologizes. In the season finale he notices his mother's gun is missing, and he goes to Karen's house. He is able to barge in through the back while his mother is pointing a gun at Karen. They are seen struggling, and later on it is revealed that he is dead when we see Karen visiting his grave.
"In order for your soul to be compromised, you need to have one." - said to Barbara Rutledege S4E5
|The Morning After||Appears|
|Breaking and Entering||Appears|
|A Kiss is Just a Kiss?||Appears|
|Guess Who's Coming To Dinner||Appears|
|When One Door Closes...||Appears|
|I Choose You||Appears|
|Friends With Benefits||Appears|
|Playing With Fire||Appears|
|What Do You Really Want?||Appears|
|Why Do Fools Fall in Love?||Appears|
|An Affair To Surrender||Appears|
|'Til Death Do Us Part||Appears|