$25 savings bond
Youth Hostel card
What Color is Your Parachute?, by Richard Nelson Bolles (a classic guide for job-seekers)
The Graduate on DVD, the 1967 film starring Dustin Hoffman
The Portable Nietzsche, by Friedrich Nietzsche, translated by Walter Kauffman
Application to join the army
Pearl necklace in a velvet box
They are all traditional graduation gifts, and/or joke gifts. The camera actually ends up becoming an essential item. Lorelai never seems to consider how Sherry would feel about her boyfriend sending another woman flowers and jewellery.