Yes, anyone can ask for it. Whether it'll be granted depends on the strength of their evidence and is up to the particular judge in question. Judges do understand that people who can't pay their debts file such cases, and most won't have any issue with reasonable contact to collect a debt - and your attempts haven't been over the top, so realistically, unless there's more to the story, I don't see a judge finding your behavior to constitute "harassment" - but be aware that stranger things HAVE happened and neither you nor we can predict what version of events HE might give the court or how convincing his side of the story will be. Since you've already been put on notice that he doesn't want contact, the better way to collect a debt owed to you is to file a civil case against him and sue him for the amounts you claim he owes. Once you get a judgement against him, you get to act within the collection laws for your state to pursue payment. Until you HAVE such a judgement, continuing to pursue him could end up being more problematic than is practical.

