<Dl> <Dd> Daughter of Greg and Jen Short </Dd> </Dl> <Dd> Daughter of Greg and Jen Short </Dd> <Ul> <Li> Ann Guilbert as Shirley "GiGi" Pirkle: Mother of Dr. Joan (Pirkle) Short; widow (husband was Winston); lived at Hidden Harbor (Retirement Community), then lived at Rocking Hill Nursing Home . Following Guilbert's death in June 2016, the GiGi character's death was written into "Eyebrow Anonymous Trapped Gem" as a tribute, and all four stories of the episode revolved around GiGi . </Li> <Li> Jordan Peele as Chad: Ex-fiancé of Colleen . Chad had some legal troubles and hired Jen's law firm to represent him . He rented his share in Colleen's apartment to Dougie, who was part of his legal team (she's currently Colleen's roommate). </Li> <Li> Fortune Feimster as Dougie: A coworker of Jen; daughter of Jen's boss; member of legal team hired by Chad; Colleen's roommate since the season 1 finale, "Crytunes Divorce Tablet Ring". Dougie is loud, boisterous, uncouth and abrasive physically and emotionally . Despite that, she showed a more vulnerable side when she came out of the closet to Colleen and Matt . She had her very first lesbian kiss with Heather, Tim's wife . When Matt moved in with Colleen and Dougie, it was discovered that Matt wrestled in high school and both he and Dougie went undefeated in their high school careers . In the season 2 premiere, "Annulled Roommate Pill Shower", Dougie challenged Matt to a wrestling match to determine whether or not she has to move out of the apartment . Dougie won the match using her patented "hook, line, and sinker" move to keep her spot in the apartment . </Li> <Li> Martin Mull as Gary Timpkins: neighbor and patient of Joan; a recent widower </Li> <Li> Susan Park as Dr. Sally Hong: Jen's OB / GYN </Li> <Li> Tonita Castro as Tonita: Colleen's grandmother . Tonita was very close to Colleen's ex-fiancée, Chad, and she also is the nanny of Lark, the daughter of Greg and Jen . </Li> <Li> Mercedes Ruehl as Mia: Colleen's mother . Married four times . Colleen fears she is turning into her mother . </Li> <Li> Bella Shepard as Lexie: one of Samantha's friends </Li> <Li> Ashley Wolff as Jenna: one of Samantha's friends </Li> <Li> Andrew McKeough as Jayden </Li> <Li> Martin Starr as Oscar: an exterminator; a field worker for "Scram! Trappers" animal control & pest removal </Li> <Li> Stephnie Weir as Bernadette </Li> <Li> Rhys Darby as Teddy </Li> <Li> Megan Mullally as Mary - Lynn: mother of Clementine; sister and partner of Spencer </Li> <Li> Nick Offerman as Spencer: brother and partner of Mary - Lynn; parent ("uncle - dad") of Clementine </Li> <Li> Josh Groban as Ian: an Irish salesman of guitars at a music store who often flirts with his female customers </Li> <Li> Russell Peters as Dr. Tak Oh, M.D.: coworker of Tim; widower (wife was Jackie) </Li> <Li> Wayne Federman as Dr. Saul Antro </Li> <Li> Angela Malhotra as Nurse Silvie: coworker of Tim </Li> <Li> Cary Elwes as Professor Sinclair Wilde: Joan's creative writing teacher since "Dinner Professor Steps Lesbian" </Li> <Li> Anne Stedman as Sangria: Colleen's stepmom </Li> <Li> Matt Cornett as Ryan: Samantha's boyfriend </Li> </Ul> <Li> Ann Guilbert as Shirley "GiGi" Pirkle: Mother of Dr. Joan (Pirkle) Short; widow (husband was Winston); lived at Hidden Harbor (Retirement Community), then lived at Rocking Hill Nursing Home . Following Guilbert's death in June 2016, the GiGi character's death was written into "Eyebrow Anonymous Trapped Gem" as a tribute, and all four stories of the episode revolved around GiGi . </Li>

Who played samantha's boyfriend in life in pieces