Princess Madeleine and Chris O'Neill Attend a Gala Dinner in Wilmington

Queen Silvia and King Carl Gustaf celebrated the 375th anniversary of the establishment of New Sweden at the Chase Center with Princess Madeleine and her fiance Chris O'Neill.

On 11 August 2009, Madeleine announced her engagement to lawyer Jonas Bergström (b. 1979). Madeleine said in her engagement interview that they became engaged in Capri in early June 2009. An engagement dinner took place on the engagement day in Solliden Palace on Öland. The engagement could only take place after Bergström had been awarded the official approval of the Swedish Cabinet Regeringen and that had been communicated to her father, the King.

The wedding was originally due to take place in the second half of 2010 but was postponed due to "many things happening in an intense period of time", mainly her sister Victoria's wedding in June. Queen Silvia denied the rumoured relationship issues. However, media reporting of the relationship issues escalated, and on 24 April 2010 it was announced that the wedding would not go ahead, and the engagement was broken off.

After her relationship with Bergström ended, Madeleine moved to New York City, where she worked for the World Childhood Foundation, the organisation that her mother co-founded. On 25 October 2012, the Swedish Royal Court announced her engagement with the British-born American financier Christopher O'Neill. On 23 December 2012, it was announced that the wedding would take place on 8 June 2013, at the Royal Palace chapel in Stockholm. O'Neill chose to remain untitled: a member of the Swedish royal family must hold Swedish citizenship which O'Neill declined.