On the series premiere, we meet Annie and Jake. After returning home from vacation, Annie goes into a rant over the fact that Jake didn't propose on the trip. While her back is turned to him, we see him on bended knee waiting to propose. Annie fails to turn around and continues a tirade against him, their friends, and his mother.

Finally, Annie turns around and accepts his proposal. However, she is humiliated when all the people she just insulted come out of hiding, including Jake's mother. After everyone leaves, Jake tells Annie they are not engaged and that he'll propose again a few days.

On their respective drives home, their friends and family judge them and question themselves due to the harsh things Annie said. When Annie is left alone, there's a flashback to when Annie and Jake met. They flirt and banter almost immediately.

At yoga with her friend, Dennah, Annie decides she needs to make a grand gesture to make up for ruining Jake's proposal. Meanwhile, Jake goes shopping with his friend, Gil, where he says he still wants to marry Annie.

Annie shows up at Jake's office where she proceeds to ask him to marry her. However, she ends up getting him fired when she reveals their recent trip to his boss not remembering he had lied about it. Another proposal ruined.

While sulking at the restaurant they met at, Jake flashes back to the first time they said "I love you". He realizes that they need to make up. Coincidentally, Annie is also at the restaurant. After making up, Jake takes the opportunity to propose again, and this time they get it right.

Later, they meet up with their friends and family where Annie apologizes to everyone for all the terrible things she said.