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According to my teacher, the sentence

They were looking forward to watching me play

is technically incorrect. My teacher suggests that

They were looking forward to watching my playing

is a "more correct" version since the phrase "watching my playing" can be deconstructed as (watching (my playing)), which can't be said about the first sentence.

My gut tells me that the first sentence is actually the correct one, but I don't have a clear reason why.

So, am I correct or not? If so, how can the first sentence be looked at/explained from a grammatical perspective?

(Also, if there are books/literature that have information regarding this, please share!)

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Both are right; they mean different things.

watching me play is a gerund noun phrase.

  • They were watching me play at the game yesterday.
  • Watching me play is not something they often did.
  • My mother enjoyed watching me play soccer.

watching my playing is slightly different in meaning.

The coach has been watching my playing to see if there are pointers he can give me for improving it.

And in this case, there is a continuous verb in the past followed by a gerund noun.

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    I agree that "The coach has been watching me playing to see if there are pointers he can give me for improving it" has a different meaning, and an odd one at that. Since you speak of "improving it," "improve me playing" is not correct, or at least without heavily changing the meaning. In this example "me" would have to be the thing that is being improved even though, given the context, the "playing" is what should be improved. I believe "my" should be used in this case and yes, slightly different meaning there as well, but only with your added context.
    – Eli Harold
    Commented Mar 23, 2022 at 20:54
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    @EliHarold Eli, Sure improving it only goes with: watching my playing. I edited it.
    – Lambie
    Commented Mar 24, 2022 at 14:23
  • (thumbs up emoji)
    – Eli Harold
    Commented Mar 24, 2022 at 14:26
  • "watching me play" can be a gerund NP, and is in the original question's sentence. But in your first example sentence, at least, it's an adjective phrase, using "watching" as a participle.
    – amalloy
    Commented Mar 25, 2022 at 9:22
  • @amalloy Yes, CGELers love calling everything with an ing a participle. For me, x was/were watching is a verb.
    – Lambie
    Commented Mar 25, 2022 at 14:05
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Both sentences are correct and the first one is more idiomatic. I think he/she is focusing on the "playing" or "play" as being the thing that is "watched." In that case you could try to argue that the first is incorrect, but the fact is that "me" is what is being watched in the first sentence. The addition of "play" is just to further describe the state of the person being watched. The sentence "They are looking forward to watching me clean my room" is surely correct, and for the same reason that your first example is correct.

The general theme here is that the format below is both correct and quite normal.

"Someone is looking forward to watching someone else do some action."

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In the first sentence, play is an infinitive, and playing is a gerund.

Both of those are "non-finite" verbs.

It's really hard to easily express the difference in meaning between infinitive and gerund. Even the Wikipedia article can't address it without being complicated, but a clue is here:

Historically, the -ing suffix was attached to a limited number of verbs to form abstract nouns, which were used as the object of verbs such as like. The use was extended in various ways: the suffix became attachable to all verbs ...

... The present-day result of these developments is that the verbs followed by -ing forms tend to fall into semantic classes.

So ... the overall concept of -ing as a gerund is that it tends to come after specific meaning-groups of verbs. The Wikipedia article provides those groups:

  • 'LIKE' AND 'DISLIKE' GROUP - adore, appreciate, (cannot|) bear, (not) begrudge, detest, dislike, (cannot) endure, enjoy, hate, like, loathe, love, (not) mind, mind, prefer, relish, resent, (cannot) stand, (cannot) stomach, (not) tolerate, take to dread, (not) face. fancy, favour, fear, look forward to
  • 'CONSIDER' GROUP - anticipate, consider, contemplate, debate, envisage, fantasise, imagine, intend, visualise
  • 'REMEMBER' GROUP - forget, miss, recall, recollect, regret, remember, (cannot) remember
  • 'RECOMMEND' GROUP - acknowledge, admit, advise, advocate, debate, deny, describe, forbid, mention, prohibit, propose, recommend, report, suggest, urge
  • 'INVOLVE' GROUP - allow, entail, involve, justify, mean, necessitate, permit, preclude, prevent, save
  • 'POSTPONE' GROUP - defer, delay, postpone, put off
  • 'NEED' GROUP - deserve, need, require, want
  • 'RISK' GROUP - chance, risk

Using playing instead of play tilts the verb's meaning towards one of those groups. When playing is said, you're possibly elevating it to an event that one can be involved in, or maybe something with some risk attached, or possibly one of the above shades of meaning.

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