I dated this guy for a couple years. Near the beginning of our relationship, he had some financial struggles. I wasn’t hurting for money (and he knew that but never asked) so I let him know that he can ask to borrow money from me if needed. He declined at first but ultimately ended up borrowing some money from me (a couple thousand). I understand and accept that I shouldn’t have lent such a large amount of money, but I loved him and knew it wasn’t in his character to just take the money and run. We had agreed to have him pay me back within a couple months (monthly payments). He was working part-time but wasn’t making much more than minimum wage.

Weeks later, he told me that he wouldn’t be able to pay me back per our payment plan and asked if we could push it back. I told him to take his time and that I didn’t expect him to pay it back any time soon. I wanted him to focus on school and work—I didn’t want him to stress about owing me money. I saw our relationship continuing far into the future so it didn’t bother me. We never rly spoke about the borrowed money again throughout the rest of our relationship. He maybe brought it up a total of 3 or 4 times saying that he felt bad he couldn’t pay me back right away.

A year later, he took a break from school and began working full time. I know he had made enough to pay me back but I knew he wasn’t planning on working when he went back to school so the money he was making during his gap year was to sustain him for the duration of his schooling once he returned. A year later, he went back to school and our relationship was rocky. It had now been about two years since I’ve lent him the money. I broke up with him because he wasn’t putting effort into our relationship. We ended on good terms but kinda awkward. We talked a lot at the beginning of our breakup but now we don't talk and he never brought up the money. About two months after we broke up, I asked him if he could pay me back. At the time I asked him, we were still talking every now and then. When I brought it up, he apologized, said he forgot and asked if I wanted the money in full now. Knowing his situation, I said that I didn't expect him to pay it all back now. He said he could maybe start paying me back in the summer but to let him know if I need some of it or all of it now. I told him I understood his current financial situation and didn't expect to take money away from him right now when he doesn't have an income. He said thanks for understanding, and we haven't really talked since then.

It's been a while since we last talked and it doesn't seem he's making an effort to maintain our friendship. The last message I sent him (unrelated to this) was left on read and it doesn't look like we'll be talking or hanging out any time soon. Since we aren't really friends now, WIBTA if I asked him to begin payments now? I'm not in dire need of the money but the extra money peace of mind would be nice.