He may want to consider reporting it to law enforcement as harassing phone calls.
Florida State Statute 365.16 describes obscene or harassing telephone calls as:
Making a call without conversation or disclosure of identity and with the intent to harass, annoy, abuse or threaten. Making a call with conversation and with the intent solely to harass or threaten. Making a call during which any obscene conversation or suggestions are made with the intention of offending, harassing,...
Your probation officer is right. Your chances of staying out - or getting out - of jail are greater if you have everything finished by the time you appear in court. You should consider hiring an attorney for the violation so that if the judge issues a warrant for your arrest on the violation, the attorney can set a hearing to have the warrant withdrawn and hopefully prevent you from having to go to jail at all.
Once the State Attorney's Office officially drops the charge or files what is called a "No Information," you can begin the process to get your record expunged. You can do it on your own, but chances are an attorney can get it done quicker...approximately four months.
You're right to be concerned about prison. Possession with Intent to Distribute is a serious charge and because he has a prior Burglary, he will most likely score mandatory prison if the new charges are filed (the prior Burglary adds 14 points to his score sheet and the Possession with Intent is 28 points - 44 points equals a prison sentence). Regarding a defense, this is a constructive possession case as opposed to an actual possession case, which is very helpful. His best defense is that he...
Yes, you can "date." Furthermore, should your conduct eventually progress beyond kissing, because your boyfriend is 16 and you are under 24, you cannot be convicted of sexual activity with a minor. And because he is 16, you cannot be convicted of lewd and lascivious molestation.