A long vacation is just what the doctor ordered for Bethenny and Jason, but the ups and downs that come with it are not. On the second leg of their trip, Jason decides that he has waited long enough to break some news about their new apartment and where they may have to live before they can move in. Willing to put themselves out there again, literally, Jason and Bethenny find themselves on yet another boat ride from hell. Bethenny and Jason can't seem to escape from their own personal issues and a lengthy discussion about work, life, and love forces Jason to face his deepest fears.

Bethenny decides it's time to give Jason an early Christmas present, but the gift backfires when Jason decides he may not be ready for all that it holds. When Bethenny brings up her obstacles with Jason to Dr. Amador for the first time, she understands it's time to take a step back and listen. Soon after, Bethenny leaves for the launch of the Skinnygirl Cranberry Cosmo in Aspen. Finally, when the idea of working together rears its ugly head again, Bethenny takes a lesson from Dr. Amador and learns to let Jason come to her instead of the other way around.