Season 1

Tennis player Mark Philippoussis is the prize in this dating competition featuring 13 women split into two groups: Kittens, who are in their 20s; and Cougars, women in their 40s. In the opener, Mark meets and spends an evening with the Cougars. Afterwards, he learns another group of women, the Kittens, are competing for his affections.

Mark has a pool party with the newly introduced Kittens before skating with the Cougars, and later has a date with three 20-somethings. In the elimination round, he sends a women from each group home and the competing groups find out about each other.

Mark has simultaneous dates with one woman from each group, but he must split his time between their two tables. Later, the women plan a date for their rival group that emphasizes the age difference between them.

Mark gives the women a quiz on tennis before cutting the group down to six women.

Mark goes on another round of dates before eliminating two more women. How far will the women go to make the final four?

Mark and the women go on a group camping trip with one of the women getting a private hiking trip

The women's families arrive and are given the opportunity to question Mark. Later, Mark goes on several dates that include salsa dancing, high tea and a carriage ride.

In the season finale, Mark and the three ladies travel to Australia, where they spend time with his family. After considering advice from his loved ones, Mark eliminates one woman. Then, it's time for the big decision after dates with the final two.