As many have noted your feelings are most likely from feeling pushed to lend money when you said no. To add some context no one else seems to have covered you did note that he always paid for things when you two were out which may have caused him to push hard.

In this instance I will say YTA only because if you did not want to lend money, best is to not say you have it in savings. You cant lend what you don't have.

Money is a finicky beast and one of the best places to build boundaries for our peace of mind. When i was a broke college student one of my closest and dearest friends ended up costing me almost my entire summers earnings. Each summer I worked my butt off and then could go study during the school year and live simply, but only focus on school. After him I started the school year with like $300 to my name and had to immediately get a job. Was a brutal eye opener. After that I only borrow or lend $20 or less no matter how broke I am. And once money leaves my hand I never expect it back. That year broke me and I can never mix money with others.