On April 15, 1934, Dolan married Emilie Campan Gerhard, daughter of Albert Pepper Gerhard, of
Overbrook, Philadelphia[7] who accompanied him for a while on his second trip to China.[4]
Dolan joined the
United States Army Air Forces after the
attack on Pearl Harbor.[1][4] In 1942 he traveled to
Lhasa with
Ilia Tolstoy, a grandson of
Leo Tolstoy, as a member of the
Office of Strategic Services (OSS), to meet with the Tibetan government. On December 20, 1942, they met the young
14th Dalai Lama and his Regent, the
3rd Taktra Rinpoche.[5][8][10] They were the first Americans ever to meet a
Dalai Lama.[5] Tolstoy and Dolan, who were nicknamed "Mud" and "Slug" by their fellow OSS officers, both received the
Legion of Merit for the mission.[10][11] They are considered to have gone beyond their authority in leading the Tibetan government to believe the
United States had given international political recognition to Tibet. Photographs taken by Dolan and Tolstoy on their expedition were published in A Portrait of Lost Tibet by Rosemary Jones Tung.[12]
After the Tibetan expedition Dolan transferred from the OSS to the Army Air Forces and joined the United States Military Observer Group in
Yunnan, China.[1][13] Dolan died in Chongqing, China. According to some accounts, he was killed on an OSS mission to rescue downed Allied bomber crews;[1] according to other accounts, he took his own life on August 19, 1945.[3]