Advice needed on a money issue

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I need some advice on what to do.

There's always a catch when somebody you rarely talk to starts calling more often. It goes from a few times a year to once a month, then once once every two weeks. It's never because they want to have a connection. It's because they are methodically buttering you up to get something they need.

My dad started calling more often to say hello and to tell me he was thinking about me. I thought that was awesome since we don't really talk that much. There's no bad blood--we're on good but distant terms. He started sending me baby pictures in the mail. He sent me the news article that I was featured in as an infant because I was the first baby born on that Mother's Day. He's been sending holiday cards, telling me he's worried he won't see me again since I moved so far away. This is weird because I typically go 5+ years without visiting. It's just the dynamic we've formed over the years.

Anyway, I fell into a trap because he called at 10am this morning--which is very odd because he works swing shifts so 2pm is morning for him. He was making small talk but I knew he was getting at something. I assumed there was a family death or something, but no. He called asking for money. When I asked how much he needed, he said $500 which is more than my car payment!! Times are tough, I get it. But I don't just have a random $500 laying around. I was obviously shocked and told him I wasn't sure I could afford that much and he sounded disappointed. I asked him what the situation was and he told me about overdue rent, overdue bills, expensive groceries, etc and how all of his retirement pension was turned over to the bank. There were a lot of red flags telling me that this wasn't just a temporary tight spot he was in, but rather an ongoing thing. I told him I'd have to see what I could do but I'd have to call him back. I tried to offer advice that he talk with his landlord about working something out but he seemed hesitant about going that route. That also cued me in that he's probably been behind on things for awhile. It happens, I understand, but he has asked for money in the past and I do not want to turn into an ATM.

Then it hit me that these recent phone calls, baby pictures, cards, etc. were most likely a strategy to manipulate me into forking over money. This made sense since it takes awhile for bills to pile up and for the bank and landlords to come knocking. He's asked for money in the past and I don't want him to start thinking that he can just call me up when he needs it. Money creates weird tension between people. It might be different if we were closer but we're not. He never makes an effort to visit and we hardly ever talk. I understand that people are going through things right now but he's done this before and I just think it's kind of sad and shitty that he set me up like that.

There's no way I can send $500 but maybe half? I don't know what to do. What do you guys think I should do?

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