Guest stars in this episode include Rachel Dratch, Chris Hansen, Keith Powell, Lonny Ross, and Dean Winters.
In the episode, Liz Lemon (Tina Fey) finally dumps Dennis Duffy (Dean Winters) and prowls the singles scene, where she proves to be particularly inept at picking up guys, under Jenna Maroney's (Jane Krakowski) tutelage.
Liz Lemon (Tina Fey) comes home to find her wall full of knife holes, a great dane roaming her apartment, and a complete stranger on her bed, all courtesy of her boyfriend, Dennis Duffy (Dean Winters).
The next day, Dennis walks into the staff office of TGS with Tracy Jordan, announcing he has found a new apartment and reads a heartfelt letter to Liz.
After a bit of objection, Toofer convinces Tracy to stop, handing the female character over to Josh Girard (Lonny Ross).
Rachel Dratch, longtime comedy partner and fellow Saturday Night Live alumna of Fey, the latter who was the show's head writer from 1999 until 2006,[7] was originally cast to portray Jenna Maroney.
[9][10] Executive producer Lorne Michaels announced that while Dratch would not be playing a series regular, she would appear in various episodes in a different role.
These cast members include: Chris Parnell,[13] Fred Armisen,[14] Kristen Wiig,[14] Will Forte,[15] Jason Sudeikis[16] and Molly Shannon.
Canning commented that Jack's relationship with Condoleezza Rice in the episode was a "great concept" and "offered up a good number of chuckles", although "it never became as clever as it appeared it was going to be."
Second-tier cast integration, multiple stories going on, intimations that Condoleezza Rice likes phone sex ... Another winning week for NBC's 30 Rock."
Mitovich enjoyed the fact that Jack was in a relationship with Rice, writing that another show "would build [the] whole episode around them" but that 30 Rock "made it that much funnier by playing it in the background and thus getting to be more outrageous with it.
"[24] Julia Ward of AOL's TV Squad wrote that Alec Baldwin "always knocks the ball out of the park on the acting front" but noted that "the best material" in this episode belonged to the Tracy and Toofer story.
Ward was complimentary towards Jane Krakowski, observing that her "comic timing" in "The Break-Up" was "impeccable as usual, but it would be nice to see her character get a tad more three-dimensional.