During the days before the proposal, Robert planned a picnic in Plaza de Cesar Chavez for Jenna, which would finish in front of Agenda Lounge. Robert chose the park because it had a triangular section that reminded him of a park Jenna showed him that she would walk to with her family when she was younger. He chose the lounge because it was where he first truly knew that Jenna was a very special individual that he would definitely like to spend more time with.

While he wasn't clear how they would get to San Jose and to Agenda without the whole plan being given away, Robert asked many people to help out, including his brother, George, and his fiancee, Kara, who would be there to take photos.

The night before the proposal, Robert was at the Niners/Texans game with Dylan when he had a great idea: the two of them would call Jenna after the game and ask Jenna if Robert and her could accompany Dylan and Tracy to a special picnic.

The next day, after visiting the Cheese House for sandwiches, Dylan called to cancel, "expectedly". Once Robert and Jenna got to the park for their picnic, Jenna started talking about candy, which was perfect, as there was a candy shop near Agendas that Robert decided to pretend they were walking toward.

Once they got to Agenda, Robert did his best to remember what he'd wanted to say, got on a knee, and took out the ring.

By the way, she said yes!

Once Robert proposed and Jenna shared the news with her sister, Molly, she called her mom, Gwyn, who invited the newly engaged couple to see them at The Wine Room in Palo Alto. 

When Jenna and Robert arrived, they were escorted to the back to have more room to sit down and celebrate.  Little did Jenna know, dozens of her friends and family were waiting to celebrate the good news!