OcRam,

Yeah that is the bad thing about graduting in MAY. However, He has 3 options:

(1) Apply for H1 in April and then during his application process he gets 60 days of Grace period..But in his case it won't do good as H1 does not begin until October 1. So, He will have to go out of country and come back with H1 visa (If H1 application gets approved.)

(2) If he wants to go back to school, then he has 5 months of grace period (only to go back to school-Not H1). So, he can join any university for August and get I-20 before OPT expires. This way his Status will be a regular F1. Then start schooling from August.

(3) The most popular option: Join School for any other degree in August. Also apply for H1 too. Even if H1 gets approve in June/July he can not work till October 1 and till then he will have to maintain full time F1 Status. After October 1 he can start full time job again.

NOTE: Durgin Grace periods, You Should not Work At All (Legally...cash ma bhae thikai cha but is risky). These are the rules I know for sure...But please do consult your school's DSO.

Hope this helps.