Flowers
$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
Disposable camera
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.
The Annotated Gilmore Girls 