WWYD: The Deadbeat Boyfriend

Back in February, I regrettably loaned my boyfriend (at the time) $700 to help cover his rent. Which, by the way, is INSANELY cheap for a Brooklyn apartment, but whatever. The money was needed because he had been fired from his job at a bar in January, and so had no income or savings to pay February’s rent.
I am extremely wary about spending large amounts of money, but I’ve been in scenarios before where I just didn’t have the money and had to borrow from a friend (twice — both times it was when I was first moving into an apartment and they asked for a TON of money up front). But! Both times I repaid the money in full, and almost immediately — because I’m not an asshole.
Thankfully I made him sign a generic loan document (that’s a pretty big sign that you shouldn’t loan your boyfriend money — you don’t trust him to repay you to the degree that you make him sign something) when I handed over the money. It’s now July, and I’ve seen $0. I’ve, obviously, broken up with him already, and he is mad/sad as a result, but now I have to take him to court over the money.
My question, finally, is this: He is, to my knowledge, still unemployed or getting paid in cash under the table. When the court rules in my favor, what will happen after that? What happens as a result of a small claims court ruling? — L.

I’m not a lawyer and won’t pretend to be one. Here is a helpful pamphlet on how small claims courts work in New York. See page 12:
COLLECTING YOUR JUDGMENT: WHAT DO I DO IF I WIN A JUDGMENT?
The winning party, or judgment creditor, will receive a “notice of judgment.” The notice of judgment will include the judge’s decision as well as information regarding enforcement officers and ways to collect your judgment. You must read all the information printed on the notice of judgment before you begin your collection efforts. Winning a judgment does not guarantee payment; however, it does give you the right to collect it. A money judgment is legally enforceable for 20 years.
HOW CAN I COLLECT MY JUDGMENT?
First, contact the judgment debtor and request payment of the judgment amount. If the judgment debtor refuses to pay the judgment amount, you may need the services of an enforcement officer.
But that’s all stuff that you can just look at on your own.
From what I can tell from this situation, your ex-boyfriend has been unemployed for half a year now, and if he’s not earning money and if his unemployment check is going to pay the bills he has now, I imagine that he has found it difficult to pay you back in a timely manner. Or he might be a jerk — I don’t know him. But have you two tried working out an alternative plan that won’t involve you having to pay court fees? For example, have you tried working out an installment plan? That might be a better option than having to deal with the court process and, if your ex-boyfriend still can’t pay you back because he is unemployed, having to pay an enforcement officer to seize whatever assets your ex-boyfriend has as payment (if he has any).
If I were in this position, I’d seek out alternative routes of getting that $700 back before taking any legal action, but to be perfectly honest, I probably wouldn’t go to court. I have a lending rule: I only lend out money I know I can afford to lose. If I couldn’t have afforded to lose $700, I would have said, “Boyfriend, I can’t afford to lend you $700, but I can lend you $200. You’ll have to figure out the rest somewhere else.” I’ve been burned before, and this lending rule has prevented me from being burned again. If you haven’t already, I would suggest making a rule for yourself as well.
Email me your WWYD experiences to me with “WWYD” in the subject line. See previous installments.
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