I have been friends with this person going on 12 years. I met him when I was 16 (now 28) & he is (33). I moved at 20 & we lost touch for about 7 years & then he found me on FB & we've been keeping in touch ever since. Even though we didn't keep in touch, I remember us having a close friendship. In the past 7 months since we've reconnected, he's asked me for quite a few favors, all which involved me loaning him money. First he needed $300 for legal problems and of course us being friends for so long I said I would help him. He did offer to pay me back, but at the time I felt if the shoes were on the other feet he would do the same for me so I told him he didn't have to. Then a few days later I received a text that he needed another $400 for the same legal problems. Shortly after, he asked if he could borrow $80. He was very grateful for all the help I was giving him and insisted on paying me back, but I told him to just be there for me when/if I really needed him. Then I received a text a day before my birthday (April 1st), I thought it would be him checking in to see what I would be doing on that day, but instead it was a picture of a pair of sneakers that he wanted me to buy for him on his birthday (April 12th). I responded jokingly "hey what about my birthday, what you getting me?" And he said, "tell me what you want I'll send it." But me being the type of person I am (humble) told him all I wanted was a happy birthday wish, no gift necessary. He said OK and then went on to tell me about the shoes and asked me if I could buy them for him. I never agreed and just changed the subject. Then a week later I received a text asking if I could get him some Burberry glasses that cost about $100 more than the sneakers he originally wanted for his birthday. At this point, I'm starting to feel like he's taking advantage of my kindness. I call him out on it and his response was that I offered to help all the other times (which is a lie, he asked) and what I was saying was very insulting to him. Then he goes on to ask me to buy the sneakers because his birthday is a big thing to him & he would do it for me. I didn't respond. Then I wake up to a text the following morning that said " Wow, I guess you dont really give a f*ck smh". Is he serious?! I mean haven't I been generous enough? Again we have been friends for a very long time, and he says that he would do the the same for me but I never ask so how would I know if that's true. Im not sure how to handle him. I dont want to ruin our friendship but I didn't think our friendship would be so costly. Am I overrating? Should I get him the sneakers for his birthday?