Lent A Guy Money. Not Getting It Back

Hello,
This guy from high school messaged me randomly on Facebook 6 months ago asking to borrow $50.
I lent to him in good faith. He returned it.
He then continued asking every month, I did because I just wanted to help the guy out. He always paid it back sometimes late.
This time he asked for the most, $300, & his facebook vanished. He sent a random message at midnight, "I need your help, I got hacked". I woke up next day & it won't let me message him.
I don't have his phone number, just Facebook & the venmo where we transferred money.
I'm guessing he does not plan on returning it, but deleting his whole Facebook over $300 seems alot.
I'd like to give him the benefit of the doubt but he hasnt messaged me yet or tried to get a hold of me thru venmo.
What are my options? Can I take him to civil court? I can find his friends/family on FB, should I ask them?
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