Walden meets another young, drunk girl and drives her home where her grandmother receives them. An unexpected turn of events make Walden find her attractive while Jake gives Alan big news about his brand new job.
Alan tries to get over the break up, and Walden decides to help him with that and borrows his credit card to him. Alan gets a change of looks and meets a new lady "friend".
After some time of thinking and decision making Lindsey decides to break up with Alan leaving him devastated. After a short period of denial Alan finally accepts the break up and takes his own little revenge on her.
Valentine's day is approaching, and Alan wants to make it special for Lindsay. Unfortunately, his plans go awry at the last minute. Kate is back in town and wants to meet up with Walden, but can he convince her to take him back?
As Alan gets increasingly comfortable living in the beach house. Walden wants to invest in his girlfriend Kate's fashion career, without her discovering that he is billionnaire Walden Schmidt rather than broke Sam Wilson, as he has led her to believe. The stress of this deception begins to affect Walden's health.