Coincidentally I just watched the Seinfeld episode where Jerry tries to dump a male friend and he cries, so Jerry backs down.
I've dumped a friend before - worse than ending a relationship. Wish I hadn't done it in quite so dramatic a way, but like you, she wasn't taking the hint that I was avoiding her! 4 years on I prefer life without this person in it. Still, I was definitely the bad guy - and I lost other friends because of it because she was the 'injured party'. Ho hum.
Is there any specific behaviour that you could pick him up on. e,g, - when you make fun of my plans, I don't like it and then I don't want to spend much time with you.
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