My boyfriend asked me to pay his phone bill for him, 3 times, saying that I would get my money back when he got it.
The total amount is $300.00.
I have been trying to get the money back for months. We are now broken up and he is refusing to pay.
I have the bank statements saying the amounts I paid and the dates.
Is my case strong enough the take to small claims court? And what would be my next steps?

Most likely, you go to the small claims court get a form and fill it out and file.