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The sentence I want to talk about is:

"I watched them playing with my basketball"

Don't these kind of sentences have two meanings? Doesn't this sentence mean either

"I watched them while they were playing with my basketball"

or

"I watched them while I was playing with my basketball"?

To not cause any ambiguity, I would say "I watched them play basketball" to mean "I watched them while they were playing basketball", and I would use "I watched them playing with my basketball" to mean "I watched them while I was playing with my basketball"

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Either interpretation is possible, but in speech context, intonation, and other prosodic features that map to syntax would make fairly clear what you meant.

I watched them playing with my basketball.

could mean

As I played with my basketball, I watched them.

I watched them as they played with my basketball.

There are other ways of expressing this idea, so that it is fairly unlikely that this pattern would be used in contexts where it could be misunderstood.

To allay Weather Vane's doubts:

I watched them, feeling the urge to pee.

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  • Yeah, you added a comma. I watched them feeling the urge to pee.
    – Weather Vane
    Jun 29, 2018 at 20:43
  • The comma is irrelevant though people may say otherwise. Punctuation is not grammar. It is merely a set of imperfectly agreed-upon conventions. It could stand for a thoughtful pause or it could reflect syntactic relationships. Any insistence that it be the one or the other is mere fiat.
    – Tᴚoɯɐuo
    Jun 29, 2018 at 20:45
  • Thank you. Should I pause between "I watched them" and "playing with my basketball" when I want to mean that I was the one who was playing with the ball? I don't think that it is needed.
    – Fire and Ice
    Jun 29, 2018 at 20:58
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    If you want playing with my basketball to mean "as I played with my basketball" then it would take more than a simple pause to indicate that it was you playing. There is much opportunity for ambiguity here, even with a pause. Context would be key. You could begin the sentence Playing with my basketball, I watched them and in that case it is almost assuredly going to be understood that you were the one with the ball.
    – Tᴚoɯɐuo
    Jun 29, 2018 at 21:22
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    @Tᴚoɯɐuo Eats shoots & leaves. Eats, shoots & leaves (with a nod to Lynne Truss) Irrelevant! Surely not!
    – Ronald Sole
    Jun 29, 2018 at 23:52
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The original sentence seems to answer the question, "What did I watch?" I watched them playing with my basketball. I would be very surprised if anyone interpreted that sentence any other way in an ordinary setting.

There are ways to force a different interpretation, but they almost all require breaking up the perceived relationship between the noun "them" and the verb "playing". For example, I watched them while playing with my basketball.

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  • Thank you. Native speakers can use that structure in my experience for meaning that they were the one who was playing. For example: "I watched them using my binoculars". This can mean that I was the one who was using the binoculars, and I guess most people would understand it that way.
    – Fire and Ice
    Jun 29, 2018 at 21:17
  • @FireandIce, That example is a bit different because binoculars has an obvious possible connection with the verb "watched".
    – ScottM
    Jun 29, 2018 at 21:37
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    @Fire - Yes, sentences like this can be ambiguous. Usually it's no problem, though, because context provides enough clues to tell which interpretation is correct. Consider: I watched them using my binoculars. I started to get nervous. "If one of them drops my expensive binoculars," I thought to myself, "then I will be very upset!" Any problem figuring out who is holding the binoculars now? That said, until you read the article, newspaper articles have no context, leading to some silly headlines, like STOLEN PAINTING FOUND BY TREE.
    – J.R. ♦
    Jun 29, 2018 at 21:39
  • @J.R. I see. Thanks. That reminds me of a recent video title on Conan O'Brien's youtube channel haha. youtube.com/watch?v=Py-Fjx3ttxU They most likely did it on purpose though.
    – Fire and Ice
    Jun 29, 2018 at 21:47
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Linking words are needed for these kinds of situations, they help us to be understood in a proper way.

I watched them drinking my coffee is a sentence in which the action (verb = drink) reverts to the object: them.

I watched them while drinking my coffee is a sentence in which the action belongs to the subject: I.

So, that's why we use them.

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In a Wikipedia article about garden path sentences, parsing is explained:

When reading a sentence, readers will analyze the words and phrases they see and make inferences about the sentence’s grammatical structure and meaning in a process called parsing. Generally, readers will parse the sentence chunks at a time and will try to interpret the meaning of the sentence at each interval. As readers are given more information they make an assumption of the contents and meaning of the whole sentence. With each new portion of the sentence encountered, they will try to make that part make sense with the sentence structures that they have already interpreted and their assumption about the rest of the sentence.

That's what's going on in your sentence:

"I watched them playing with my basketball"

If that means that the people you were watching were playing with your basketball, then the sentence will probably be parsed correctly on the first read. However, if you mean that you were watching the people while you were dribbling your basketball, then there's a good chance that meaning won't be caught on the initial read.

Other answers have already delved into good ways to fix this. You could reorder the thoughts in the sentence, or add additional words to clarify what is going on:

  • As I played with my basketball, I watched them.
  • I watched them while I played with my basketball.

As for the additional example in your comment ("I watched them using my binoculars"), that could be rephrased, too, to make the intended meaning more apparent:

  • I watched them through my binoculars.
  • I watched them as they looked through my binoculars.
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