The magazine obtained the photos from Kelli Allman (née McCormack), Obama's classmate at Punahou School in Hawaii.
[From left: Greg Orme, Kelli Allman, Barack Obama and Megan Hughes at Allman’s parents’ house in Honolulu.]
The image, taken at Allman’s parents’ house in Honolulu, shows a smiling Obama with his arm around date Megan Hughes, along with Allman’s date, Greg Orme, a fellow varsity basketball player and Obama's best friend at the time.
Allman also shared the note the future president wrote in her high school yearbook. "It has been so nice getting to know you this year. You are extremely sweet and foxy, I don't know why Greg would want to spend any time with me at all! You really deserve better than clowns like us; you even laugh at my jokes!"
For more pics, go to Time.com!