Antonio Pierce, an NFL linebacker, met Jocelyn Maldonado during a celebrity appearance at an ESPN Fantasy Football Draft. Maldonado, a model at the event, instantly caught his eye. Pierce and Maldonado (who now hosts Mets Weekly) were inseparable over the next six months.

In February 2007, Pierce treated Maldonado to a helicopter ride above Manhattan before dining at Brooklyn's The River Café. Famous for its chocolate Brooklyn Bridge cake, Pierce conspired with the restaurant's manager to place the engagement ring atop the confection, which was covered with pink rose petals.