<Li> Michael Mosley as Chuck, Andrew's friend . </Li> <P> Peter Chiarelli initially wrote the script for the film in 2005 . In May 2007, it was announced that Sandra Bullock had been given a lead role for The Proposal . Julia Roberts was originally approached by producers for a lead role in the film, but later declined . Nearly two months after the announcement, it was reported that negotiations were being finalized for Ryan Reynolds to star opposite to Bullock . In January 2008, Touchstone Pictures signed Anne Fletcher to direct the film . It premiered on June 1, 2009 at the El Capitan Theatre in Hollywood, California . </P> <P> Filming for The Proposal initiated in April 2008 in Rockport, Massachusetts . In the oncoming days leading to production, areas of the town were temporarily remodeled to represent Sitka, Alaska, the setting of most of the film . Principal photography officially began on April 9 at Bearskin Neck, where it continued over a period of 24 hours . Filming continued at the Motif Number One building on Bradley Wharf (April 14--16), the Haskins Building (April 15--18), and the central business district of Rockport (April 17). Principal photography relocated to Manchester - by - the - Sea, Massachusetts on April 22, where it resumed over an approximate period of two weeks . In response, city officials accommodated the producers by renting out all publicly owned parking lots . Filming for The Proposal was shortly delayed after Bullock and her husband were involved in a car accident . The wedding scene was filmed in a three - story twentieth century Victorian home; photography took place at the residence for three weeks . In an interview with the New York Times, the owners of the home stated that Nelson Coates knocked on their door asking for leaves . Initially, the owners directed Coates to other residences in the area; however, they eventually gave the film's producer a tour of the house . Production occurred on the first floor of the home . Outside of the Cape Ann area, filming took place in Boston, Massachusetts at the State Street Bank Building and in Lower Manhattan in New York City . The Proposal contained 350 special effect shots, and some parts were edited using computer - generated imagery . The score to The Proposal was composed by Aaron Zigman, who recorded his score with the Hollywood Studio Symphony at the Sony Scoring Stage . </P> <P> As part of an extensive advertising campaign, Reynolds discussed taking part in the production of a nude scene . The scene was filmed in a period of three days, and took approximately twelve takes to complete . Expressing that she was initially nervous, Bullock stated in an interview with Sky News that "when everyone else acts like it's just a normal day it really helps you relax ." Although she revealed that producers provided them with fig leaves, Bullock stated that they would continuously fall off . She added, "You could literally see everything ." Similar sentiments were expressed by Reynolds, who in an interview with People, stated, "Filming a scene that involves being entirely naked and takes a couple days can be a little awkward ." He continued: "Thankfully you're there for so long and you're doing it for so long that you dispense with the awkwardness pretty quickly and start to have mundane, normal conversations--the difference being you're not wearing pants ." </P>

Where was the movie the proposal filmed at