Do I have any chance at getting back the money I was promised?

I'm sure cases like these are a dime a dozen, but I'm a sucker for malicious compliance, so I'm wondering if my case "has legs" so to speak.

I began lending money to my friend this December. At first I was paying him cab fare to get from his class to my house. Ten dollars here, ten dollars there, etc.

In March, I expressed a slight concern about getting paid back, and was told to make a note of what he owed me along with a promise to pay it back once he obtained a stable job. I trusted him because at the time he was doing a fast track course which would've given him a well paying job in a few months time if all went accordingly.

On the 3rd of June we were making plans to see a movie. I had been under the assumption that since he said he had tickets ready to purchase. I was then told that the money had been spent on gas and now I had to spend 43 on the tickets (it was a premier showing at a fancy theater despite me saying I would be fine with a cheaper option)

He graduated in early June and earned a relatively well paying job close to where he lives. I'm still happy for him about the circumstances. We celebrated with a party, and I lent him money to the tune of around 140 bucks From June 8th To August 8th, I would lend him money under the constant promise of it being paid the moment he obtained his first paycheck.

When he got his first paycheck, he spent it on a hundred inch tv. He got mad at me when I asked about the money I was owed and said he "already told me he can't pay me back yet" because he had told me about the tv.

Yesterday, we had a fight and Im pretty sure this is like, the platonic equivalent of a breakup. I don't want to see him again.

My mother told him not to come by unless he had the money he owes me. He said he needed clarification on what was owed. I went through my bank history and collected nine months of transfers from my bank to his.

His response to the screenshots, to quote:

"I'm not obligated to pay anything as we've both put funds towards things but thank you! Good luck with small claims court."

So, re: me being a sucker for malicious compliance, I'm wondering if there is any possibility of getting my money back through legal means? The sum is just a bit over $500.

I am on disability, and seeing that the sum owed is the cost of a months rent for me (my family and I split payment), it'd be a huge help to get this money back. I know a written IOU, a couple screenshots and some words via discord probably aren't IDEAL resources to go off of but honestly all I want is the closure of a professional answer of if I'm gonna see my money come back to me or not.

Thanks in advance. If anyone needs screens I can try to DM upon request.