Alan, Charlie and Jake are sitting in a coffee shop talking when Evelyn walks in with with a man. The boys assume that this is her new boyfriend and decide that they do not want to see their mother or meet him. They try to sneak out the back door, only to discover there is no back door. They hide in the bathroom. The boyfriend comes in and Jake is in the stall, Charlie is pretending to use the urinal and Alan is washing his hands. The boyfriend uses the urinal, washes his hands and then states that their mother would like to see them once they are finished in here. They reluctantly go out into the shop and stop by and see their mother. She introduces them to Teddy, stating that he travels a lot and she just sold him an apartment here. They state they need to get Jake home and leave.
Later on the boys are watching TV and Teddy calls them. Charlie won't answer the phone so Alan does. Alan gets excited and asks Charlie if he is sure he does not want to know what is going on. Charlie says no, that he is busy. Alan tells Charlie that Teddy is taking him to Las Vegas in his private jet to stay in his condo and he has ring side seats to the fight at Caesar's Palace. Charlie still states he is not going.
The next day, Alan is still excited about is upcoming trip and Charlie is out on the deck. Teddy arrives and tells Alan that the car is waiting, but he would like to talk to Charlie. Alan is so excited that he goes and sits in the car. Teddy asks Charlie to come along and they talk. Charles decides to go.
In Las Vegas, Alan, Charlie and Teddy are sitting ring side waiting for the fight. Evelyn calls and Teddy lies and tells her he is San Francisco. He then asks the boys to lie to their mother about this trip, neither one has issues with the request. Teddy offers each on a piece of his $5000 bet. Charlie states he will go in for half and Alan agrees to go in for 20 to 25 dollars. Then the fighter that they bet on (The Russian) gets knocked out.
In the bar, Teddy can't believe that the fight only lasted 18 seconds. Alan is playing the slot machine and becomes excited that he broke even. Teddy shows the boys the diamond ring he bought for their mother and tells them he wants their blessing. Alan says yes and Chalice is a little more hesitant. Two dancers show up and Teddy says he is taken but he will pay for the boys, which makes them happy.
Back at home, Alan returns home from work and catches Charlie looking at a "Modern Bride" magazine and Charlie notes that he was thinking about letting Mom have the ceremony here. Alan then shares his ideas for the wedding. They both agree that they are doing this for Teddy not their mother. Berta goes to leave for the day and they share the good news with her. They call Teddy and find out that their mother turned him down. They go over to their mother's home to talk with her. They use their emergency key to let themselves in. Evelyn comes out of the bedroom in a robe; she tells them that this is not a good time. They state that they want to talk about Teddy. Hugo stumbles out of Evelyn's bedroom and she introduces him to her kids. He is not pleased that she has kids. She tells them that Teddy wants to settle down and she wants her freedom. Charlie can relate to that. She notes that there are some areas that Teddy does not measure up to Hugo; it is the biggest she has ever seen. All of a sudden Hugo keels over, dead. Evelyn picks up the phone and calls Teddy. She asks him to forgive her and makes plans to meet him at his house. Alan and Charlie are stunned. They question her decision to leave Hugo lying on the floor to visit Teddy, but she responds that she can't very well have Teddy over to her home with Hugo there. They are thrilled that Teddy is back in their lives.