When Toby turns sixty eight, Andie decides that marrying him will make a pretty nice 70th birthday present. But execution of this plan eludes her for a little while, until she realizes she needs to recruit co-conspirators. There's no shame in admitting she can't do it alone. And there's something that feels right about making it a community effort, in any case. This is not just about Andie and Toby, star-crossed lovers. It's about the family they're a part of. She calls up Josh and asks him if he can have Team Andie T-shirts printed. He promises to get right on it, the delight in his voice unmistakable, so infectious that she forgives him when she learns that he in fact staffed out the task of getting the shirts printed. Josh Lyman is a very busy man these days.
At the first meeting of the co-conspirators, the first debate is the most momentous: when do they inform Toby that he is going to get married? Andie favors waiting until the day of the event, revenge for the time he ambushed her with a house she had no use for. Or any of the other times when he did something deserving of her ultimate revenge, there have been plenty of those along the forking path they've walked together. C.J talks her down. Marrying him now, she says, marrying him after all these years of being linked by something less complicated than marriage, but no less real... that has to be about forgiveness, right? She can't give him the thing he's begged of her for thirty years and then be petty about it. That would miss the point. And after all, she does have to allow the possibility that Toby will say no, since she's done the same to him dozens of times. If she has Sam lure Toby to some hotel bar, only for him to bumblingly lead Toby into an adjacent ballroom where friends and family await, it would ruin things if he turned her down. Among other problems, the caterers wouldn't give a refund. It is a little bit cruel, but Andie has always admired C.J.'s willingness to be the cruel one when her friends need it. Very well, she will give Toby some time.
But not too much time. Not enough time for him to accept and then have second thoughts. Not enough time for him to get involved in the wedding planning, to object to the fanfare and inject the day with some badly needed sobriety. They settle on a week. A week before his seventieth birthday, Andie will blindfold Toby and drive him to the house where he once proposed to her, and then she will reciprocate. For the second time. What could possibly go wrong? On reflection, Andie decides it's better if she doesn't answer that question.