Five years later - five years of doing odd jobs, collecting playbooks, attending friends’ weddings, and memorizing songs from Martinelli’s shows and films - Howard convinces her to return home to Los Angeles for his upcoming wedding to another celebrity. For her brother’s sake, Peggy agrees to being made a bridesmaid - for the twenty-eighth time, a fact of which she reminds him more times than that - since his fiancée is estranged from her family.
Having been part of the highest social classes for her whole life, it doesn’t surprise Peggy that her brother would marry someone famous - but she certainly doesn’t board the Stark Industries jet home expecting to be greeted by the object of her own affections. But by thinking that her feelings would be the most significant complication, Peggy neglects to allow the possibility of what ultimately happens: Angie falling in love with her.
She knows better than to let herself dwell on the lack of real romance in her relationship with Howard Stark, because frankly, she doesn’t want to chance losing someone else that matters to her. When he proposes, she thinks of the stability she’s been wanting to have in her life - stability her life’s never had - and gladly nods her assent.
Looking at her fiancé’s younger sister and feeling the feelings she’d long since learned to feign for men was definitely not part of that agreement, but she’s as powerless as anyone to keep herself from falling - hard.
He does, however, know when he finds someone he wants to keep close, and after finding solace in a refreshingly humble actress, he figures it’s as valid a choice as any to ask her to marry him. Hoping it’ll knit what’s left of his family a bit tighter together, he insists that Angie and his sister spend some time together and get to know each other. But as time goes on, the Girls’ Nights start to look less like sisters-in-law acquainting themselves and more like two girls stumbling around crushes, and he realizes that he’s got to find a way to make the pennies drop.
The question, then, is how to get them to admit their feelings - which, being unrelated to technology, business strategy, and/or Star Wars, is really not Howard’s area of expertise...but that’s not to say he doesn’t have some Jedi mind tricks up his sleeve - and he's certainly not afraid to use them.