Robby Love, who appeared on the first season of Millionaire Matchmaker, is back and seeking Patti’s help, but it is obvious that Robby has not changed. Patti refuses to help him and thinks he’s a big kid that won’t grow up.

Instead Patti turns her attention towards two new millionaire clients — Daniel Maltzman, a celebrity artist whose works sell in the range of $15 to $20k a piece, and Chris Palzis, a mellow surfer who grew up in Hawaii and doesn’t care about money or status just as long as a good wave is about to break. Daniel grew up in Beverly Hills and has been immersed in LA’s celebrity culture his whole life. Daniel is obsessed with celebrities and fame, which annoys Patti. Chris is the author of a line of children’s books called the Goodness Gracious Club, and although he’s about to turn 40, he’s only dated women in their early 20’s.

After meeting both millionaires, Patti feels that Chris would benefit from dating a women closer to his own age and Daniel needs to stop with the incessant name-dropping and date a girl who isn’t impressed by who’s walking down the red carpet in front of them. Patti sends Chris to meet with one of her specialists, therapist Mitch Newman, who challenges Chris’s ideas that older women “have baggage” and can’t keep up with his active lifestyle.

At an intimate mixer that Patti has put together, both men are put to the test. Chris winds up choosing a woman in her mid 30’s and Daniel chooses a woman with no connection to the Hollywood lifestyle. Daniel takes his date to a posh restaurant in Los Angeles and then to his art gallery for a special surprise. And much to Patti’s dismay, Chris takes his date surfing.