I have completely re-edited my post and deleted my comments. I hope this isn't breaking any rules, if so please inform me and tell me what to do.
My boyfriend goes to school and helps take care of his brother, and all of his family is in the UK. I also go to school and help take care of my brother, and I am the only thing he has in the US. He tries to come see me whenever we both have off, no one feels comfortable with me travailing international by myself. He came to the US Nov 1, 2016, and stayed until Jan. 28, 2017, on Feb. 7, 2017, he applied for the B2 visa which was denied for not having enough ties to the UK, looking back I have no idea what we were thinking applying that early.
We just wanted to be able to book a ticket early before they got super pricey (we were going to travel July/Oct time) on March 1st he applied for ESTA which got denied. We did talk about getting married seeing as that's always been the plan just not this early, but we thought it might look staged because of the visa denials previously, and we still would have to wait a year to get married. Would the fiance visa still work if he got married at the courthouse and had an actual wedding later on? Do we have any other options? What are the chances of the ESTA being approved in Aug? Should we wait longer to apply for the ESTA?