After becoming pope in 1503, Pope Julius II aimed to find Felice a second husband. This was a difficult task because Felice was not a popular choice for marriage: she was the illegitimate daughter of a pope and did not appear to be beloved by him, and she was 20, rendering her an unappealing match due to her older age. A match was eventually made with
Gian Giordano Orsini, son of Gentile
Virginio Orsini, Lord of
Bracciano, and the leader of two of Rome's most powerful aristocratic families. This was an excellent match for Felice as it allowed her to stay in Rome. This match was also very beneficial for Pope Julius II, who wanted to end the bloody feud between the Orsini and Colonna families. He accomplished this by gaining influence in both families by marrying his niece, Lucrezia, into the Colonna family, and Felice into the Orsini family. Gian Giordano was 20 years Felice's senior, and worked as a
condottiere. He had previously been married to king
Ferdinand I of Naples' illegitimate daughter, Maria D'Aragona of Naples, who had born him three children: Napoleone, Carlotta, and Francesca, before dying in 1504. Felice's dowry was 15,000 ducats, which was worth less than the dowry given to Lucrezia, who had received 10,000 ducats, but also a palace at the church of
Dodici Apostoli, and the town of
Frascati. Scholars believe that Pope Julius II's unfriendly treatment of Felice was due to his desire to differentiate himself from his predecessor and rival,
Pope Alexander VI, who had practised extreme nepotism, particularly by parading his daughter around Rome. Felice's father further humiliated her by forbidding any major festivities for her wedding and by not attending. The wedding took place on the 24 and 25 May 1506, and was held at the Cancelleria (modern: Palazzo Sforza Cesarini), a palace then in disrepair. Some scholars have hypothesised the marriage as an unhappy one, claiming that Gian Giordano mocked Felice for being the bastard daughter of a pope, but evidence suggests that Gian Giordano came to like Felice's "managerial qualities and diplomatic skills", and encouraged Felice to pursue her ambitions. In the first two years of marriage Felice's main objective was to give birth to a son, who would guarantee her security within the Orsini family, exclude her stepson, Napoleone Orsini, from receiving the Orsini lordship, and make her the regent of the family should Gian Giordano die while her son was a minor. Without a son, Felice risked losing the power and wealth gained from her marriage.
Reconciliation with her father When Pope Julius II refused to attend the wedding he arranged for his daughter and Gian Giordano, it is believed that Felice interpreted this as a lack of respect on the part of her father and was resentful towards him. These feelings created a rift between Felice and her father that lasted for a few months. In an effort to reconcile, Julius II invited Felice and her new husband to the Vatican in late June 1506 and held a lavish banquet in their honour. Following this reconciliation, Julius II frequently made Felice the guest of honour at various parties in Rome, where oftentimes she was the only woman present. Felice's presence at various events in Rome throughout this period helped elevate her to a position of power within the Vatican court. In addition, the Pope gifted Felice with extravagant jewellery and significant sums of money, including an item that would become one of her most prized possessions: a diamond cross originally given to her father from the
Republic of Venice.
Economic activities Castle at Palo During her marriage, Felice was given her own personal assets, which allowed her to become a wealthy woman in her own right. Her main source of income was the estate and castle at Palo, a pre-existing property in modern-day
Ladispoli. Acquired in 1509, this castle provided both income and a method through which to increase both her influence and her family's power. She did this primarily by establishing the estate as a papal residence. The castle was granted this status by her father when he was pope, and continued on after his pontificate ended. This prior use of the estate as a papal residence led to subsequent papal figures such as
Pope Leo X being hosted at the castle. The grounds around Palo were suitable for hunting, which helped to attract these prominent guests, and eventually led to the property also being recognized as an official papal hunting lodge. Felice was able to set up the residence as a hunting lodge by brokering a deal with Leo X. He agreed to pay for the necessary repairs and upgrades the castle would need to turn it into a luxury property, and in exchange, Felice allowed Leo X to stay at Palo for free. By employing the castle as a financial asset and opening it up to high-ranking guests, Felice was able to promote both the image of the della Rovere family as a whole, as well as her own image.
Grain trade Besides property-owning, Felice also used the grain trade as a source of income. This involvement in business gave Felice experience that would help to support her both during her marriage and after her husband's death. The fields on her Palo property were well-suited for growing grain, and could produce a significant amount of wheat, as attested to by the entries written by Felice's servants in the account books for the estate. However, during the 1533–1534 grain crisis in Rome, Felice's revenue suffered. The reasons for the crisis were mainly a bout of poor weather conditions and an underdeveloped transportation system. As a result, Rome had to import grain from other areas of Italy, and this often led to the price of grain being doubled. As Felice's property was located close to Rome itself, she mainly sold her grain directly to people in and around the city and was therefore affected by the bad harvest. As well, grain suppliers located in Northern Italy were able to abuse the system during this time because the supply of grain in Rome itself was so poor, allowing them to charge steep prices. This left local suppliers such as Felice in a dire situation. During this crisis, Felice had to resort to bargaining to get a better price for her grain. Felice's individuality is revealed through actions such as these, as haggling was not something upper-class women were supposed to do. Ultimately, despite these struggles, Felice was able to use the grain trade to increase her wealth. ==Role in peace negotiations between the Papal States and France==