Theater in the summer of 2010, opposite Kate Burton, Boyd Gaines and Brenda Wehle. Steggert starred as Will Bloom in the musical version of Big Fish alongside Norbert Leo Butz and Kate Baldwin. It ran for 98 performances from September 5 through December 29, 2013. Ben Brantley's New York Times review (October 6, 2013) said, "Mr. Steggert's singing exudes a radiant sincerity that transcends corn." He co-starred (as Will Ogden) with Tyne Daly in the premiere of Terrence McNally's Mothers and Sons at the Bucks County Playhouse in New Hope, Pennsylvania. It had a limited run of 14 performances from June 13 to June 23, 2013. The cast was interviewed by Theatre Sensation's Kelli Curtin: "Bobby Steggert plays the character of Will in this play. Steggert describes his character as, "a modern gay man where being a husband to a man and having children is a viable option. My character represents the progress that has been made in society. My character is strong willed, steadfast in point of view and I admire that about him." According to Steggert, this play is important because it is about relationships and families. He states, "Twenty years ago a play like this would be classified as a 'gay drama.' Now a play that addresses issues faced by gay people is mainstream. The characters in this play are interesting because they are people and not because of their sexuality." Steggert is hopeful that people that see this play will "broaden their definition of family after seeing Mothers and Sons through observing the family on stage." Mothers and Sons ran on Broadway at the John Golden Theatre from February 23, 2014 to June 22, 2014, with Steggert and Daly, joined by Fred Weller, and original director Sheryl Kaller. In March 2016 Steggert starred Off-Broadway in the title role of Adam, in Anna Zeigler’s Boy at the Clurman Theatre. Around 2016, Steggert "completely turned my back on an acting career that I had spent twenty years building." He earned a Master’s in Social Work from Columbia University and trained as a therapist at the Institute of Contemporary Psychotherapy in their Gender and Sexuality Program. In an announcement of his retirement from acting, he stated, "if I ever return to acting, it will be with this knowledge (and I hope it reminds you of your own possibilities) — that the work does not stop when unemployed — that