| 1986, January | 
| Madonna and Sean begin filming Shanghai Surprise in China produced by George Harrison's Handmade Films company |
1986, March 11 | 
| Accepting the People's Choice Awards on the set of Shanghai Surprise in London |
1986, April 16 | 
| Madonna and Sean attend the Los Angeles premiere of his film At Close Range at the Bruin Theatre |
1986, June 30 | 
| True Blue album is released |
1986, August 14 | 
| The couple outside the Lincoln Center |
1986, August 28 | 
| Madonna and Sean open in Goose & Tom-Tom at Lincoln Centre's Mitzi Newhouse Theatre |
1986, August 31 |
| Madonna and Sean play their final performance in Goose & Tom-Tom |
1986, September 22 | 
| Leaving the Ivy restaurant |
1986, October 14 | 
| Announcing the Mtv competition "Make My Video" for True Blue single during Mtv´s "True Blue Day" |
1986, November 12 | 
| "Open Your Heart" single is released |
1986, December | 
| Madonna presents her Open Your Heart video on french Tv |
| 1986, February 20 | 
| Madonna and Sean attending the screening of his film At Close Range at the Berlin Film Festival in Germany |
1986, March 26 | 
| "Live To Tell" single is released |
1986, May | 
| With Nick Kamen recording his #1 hit "Each Time You Break My Heart" with Madonna´s vocals |
1986, June 30 | 
| "Papa Don't Preach" video premieres on MTV |
1986, August | 
| Going to rehearsals of Goose And Tom Tomm in NYC at Lincoln Center |
1986, August 28 | 
| Leaving the performance of Goose and Tomm Tom |
1986, August 31 | 
| Leaving the Sardi´s restaurant´s "Closing of Goose and Tomm Tom" after party |
1986, October 2 | 
| "True Blue" video premieres on Top Of The Pops |
1986, October | 
| Leaving Le Dome Restaurant in Beverly Hills |
1986, November 14 | 
| At the Mission premiere |
1986, December | 
| Being interviewed during the "Making of Who´s That Girl" movie |
| 1986, February 21 | 
| At the Heathrow airport in London arriving to complete filming on Shanghai Surprise |
1986, April | 
| "Live To Tell" video premieres on Mtv |
1986, June 2 | 
| With Sean at the Amnesty International Benefit evening |
1986, July | 
| Starting rehearsals for a 4-nights non-public play of David Rabe at Lincoln Centre Theatre - Goose & Tom-Tom |
1986, August | 
| For Mitsubishi Electornics Madonna films totally four Tv ads - this is the 2nd one |
1986, August 28 | 
| At the Elaine´s restaurant |
1986, September 10 | 
| Accepting the Video Vanguard Award for her visionary videos at the MTV Video Music Awards in NY and LA |
1986, October 9 | 
| "True Blue" single is released |
1986, October | 
| Madonna begins filming Who's That Girl movie (previously called Slammer) directed by James Foley |
1986, November | 
| In Mtv studios awarding with cheque the winners of "Make My Video" contest |
| 1986, March 6 | 
| Madonna and George Harrison hold a press conference in London to discuss the filming of Shanghai Surprise |
1986, April | 
| At the fashion show of underwear collection by Joseph Ettedgui |
1986, June 11 | 
| "Papa Don't Preach" single is released |
1986, July | 
| For Mitsubishi Electornics Madonna films totally four Tv ads - this is the 1st one |
1986, August 16 |
| Madonna and Sean celebrate her 28th birthday and their first wedding anniversary at Gotham Bar and Grill |
1986, August 29 | 
| Shanghai Surprise is released nationwide |
1986, September 20 | 
| Attending the Commitment To Life benefit for AIDS Project Los Angeles to honor Elizabeth Taylor at the Wiltern Theatre |
1986, October 11 | 
| Making a surprise appearance on the season premiere of Saturday Night Live |
1986, November 10 | 
| Participating in an all-star AIDS benefit modelling fashion show at Barney's clothes store |
1986, December | 
| "Open Your Heart" video premieres on Mtv |
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