My boyfriend received a "2 week limited stay" on his passport . how can I get him to stay for longer?

Even with a “two-week limited stay” notation on his passport, your boyfriend may be allowed to remain in the U. S. through filing a B-2 extension application on form I-539 Application to Extend/Change Nonimmigrant Status with payment of $370 to U.S.C.I.S. I do note that a denial would automatically invalidate his present tourist visa. If he decides to go back home rather than filing an extension request, he should perhaps wait another 6 months before attempting to come back to the U. S. Also instead of him coming to the U. S. to visit you, you could always visit him in the Caribbean. Due to the limitations of the Lawyers.com Forums, Alan Lee, Esq.'s (the "Firm") participation in responding to questions posted herein does not constitute legal advice, nor legal representation of the person or entity posting a question. No Attorney/Client relationship is or shall be construed to be created hereby. The information provided herein by the Firm is general, and requires that the poster obtain specific legal advice from an attorney. The poster shall not rely upon the information provided herein as legal advice nor as the basis for making any decisions of legal consequence.