Was Robert E Lee and Ulysses S. Grant friends?

Answer 1

They were friendly but only slightly acquainted. When they sat down to discuss terms at Appomattox they first reminisced for a few minutes about times they had encountered one another during the Mexican War eighteen years before, when both served in the command of Winfield Scott, on the campaign from Vera Cruz which captured Mexico City.

Grant was a good friend of Confederate Lieutenant General James Longstreet in the "old army". Longstreet renewed the friendship after the war, and became a Republican. Grant gave his old friend several government posts. Other southerners never forgave Longstreet for this apostasy, and there are no statues anywhere in the south of the commander of Lee's First Corps, the man Lee called his "old war horse".

Grant had also been a good friend of Confederate Major General Simon Bolivar Buckner. Grant first made a name for himself in the Civil War by forcing the surrender of Fort Donelson on the Tennessee River. Other commanders had made all the mistakes that lost this campaign for the south, then boarded a steamboat and departed, leaving Buckner to surrender Fort Donelson to Grant. It was the first time Buckner had seen Grant since he loaned him the money (several hundred dollars - serious money in those days) to get home when Grant resigned from the Army. Buckner asked Grant for his terms and Grant said nothing but immediate and "unconditional surrender" were acceptable, which is where Grant got his nickname. Buckner thought Grant's failure to offer any terms was ungenerous. There is no record of Grant ever repaying Buckner for the loan. Buckner's son, Lieutenant General Simon Bolivar Buckner, Jr. was one of the two highest ranking US Army officers to die in WWII, and the only one killed by the enemy, on Okinawa.

Answer 2

No. Grant was subordinate to Lee in the war with Mexico, and they knew each other from that conflict.