"You are not defined by dating Taylor Swift. But they are defining you with a Taylor Swift song," Stern argued. Not wanting to add fuel to the fire, the actor joked, "There are dark things that happen on Good Morning America. That is not one of them." Stern suggested the show could have played an Eminem song, given that the rapper contributed to the Southpaw soundtrack. "I don't know, man," Gyllenhaal said. "I'm sure they have so much music on that show playing all the time. It's just one of those things."

Stern couldn't help himself, saying, "I feel—and this is me stepping in—you should have married Taylor Swift, and I'll tell you why…What a power couple!" Everyone laughed, and Gyllenhaal replied, "Oh, that's the reason?" Stern said he is "super attracted" to the "Shake It Off" singer, and Gyllenhaal admitted that she's a "beautiful girl." Had he been friends with Gyllenhaal when the actor was dating Swift, Stern would have told him she's a keeper. "Why didn't you have me on this show sooner?" Gyllenhaal asked.

"I would have said, 'Jake, this is The One.' Because to me, nothing is sexier than a woman who can play songs and write," Stern said. Quivers noted that Swift has written "a song" about Gyllenhaal, but the star feigned ignorance, asking, "Do I?" Quivers replied, "Well, that's what they say." Stern asked Gyllenhaal which song Swift had written about him (apparently he's never listened to the Red album), but the actor said, "I don't know...This is all Robin. She's looking it up right now. She's feverishly looking it up online."