How can we resolve the money he owes me?

I've been dating "Ryan" about a year ago . None of us has a lot of money. During the last couple months , I've borrowed some money. The total amount of the loans have been around $ 350. I think he intends to pay me back. But the problem is that no money. In his last paycheck , which made about $ 200 , which happened in a couple of days. Think of the full-time job again soon, which will significantly increase your salary, and he's going to take a loan of $ 1000 from your 401K , once you pay off your current loan , but I worry that will not be able pay me back. I'm not angry with him about it, but there is a friendly way we can resolve this? We can always work with a payment agreement , I'm sure he would be willing to do so , but that would make it sound like I do not trust him and I do really. Any advice would be greatly appreciated. Thank you.