After Vanina's breakdown, she continues to report to work, leaving her boss unsure of whether or not she is leaving for good. Jeff comes up on the opportunity to buy another house, which means more change on the horizon. Jenni has good news of her own to share, but a swift illness threatens her health and her hope for a growing family.

Only one week from the baby's due date, Jeff and team rush to make final preparations and wrap up client projects. Worried about missing the birth, they head to northern California to wait for the call. After years of research, nine months of pregnancy, and over a week of anticipation, Jeff and Gage finally meet their daughter, Monroe.

Jeff and Gage bring baby Monroe home and officially step into parenthood. After a three-month hiatus, major changes have taken place at the JLD office. Vanina is gone and they've seen a revolving door of nannies. The office assistant has also left, but not before writing a detailed criticism of his first 90 days at the office. Gage struggles to keep up with work while continuously checking on the baby. Jeff starts to get frustrated with his lack of focus, driving an even-deeper wedge between them.