Do I need an extra "about", or does one suffice?

Consider the following sentence:

I have a lot to talk about with John about his project.

Since I can swap the position of the first about to make it 'I have a lot to talk with John about', then I would end up with:

I have a lot to talk with John about about his project.

My question is, can I consolidate the two instances of about, giving me:

I have a lot to talk with John about his project.

Or do I have to keep two prepositions there, but change the second about to something else in order to make it sound less-awkward, as in:

I have a lot to talk with John about regarding his project.

Related question (now that I'm thinking more...er...about this): is the first about really an adverb, in which case, of course, I cannot ever consolidate the two?

Solution 1:

I think the verb 'talk about' is, in itself, difficult to use as an infinitive. The 'about' seems to present as an out-of-place preposition. It would be much better in this example, in my view, to use 'discuss'.

'I have a lot to discuss with John about his project'.

Solution 2:

Nothing wrong with the first one except it sounds clumsy.

The other three don't make sense but you are close with the fourth one.

I have a lot to talk about with John regarding his project.

Means the same as the first sentence but without all the overabouterage (that's not a real word)

(I have no idea about adverbs and the like, so I can't help in the technical details)