My or me + verb-ing? Possessive Gerund

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Jose asks about the possessive gerund in my Free Grammar Questions,

Which is correct?
(1) She doesn’t approve of (me) or (my) gambling.
(2) They insisted on (me) or (my) staying with them.
My answer is the possessive ‘my’.

The short answer is, for English grammar purists, that Jose is correct. The possessive pronoun “my” should be used with a gerund (a verb with -ing that is acting as a noun.) You don’t really call it the possessive gerund; it’s a gerund following a possessive pronoun.

Here’s what I told Jose:

In both cases, I agree with “my.” The reason is that the -ing word is a gerund, a verb used as a noun. So “gambling” and “staying” are both things, like a car or a hobby.

If you wrote the sentence as “She didn’t approve of my car” you would see it makes sense. If you wrote “She didn’t approve of me car” it would clearly be wrong.

However, it can get complicated. Some would argue that the pronoun “me” or “my” is the object of the main verb in the sentence, “approve.” Without an indirect object, the sentence would be “She didn’t approve of me.” This seems perfectly correct, so why the confusion?

In fact, only grammar purists worry about me or my in this situation. If you have a really strict teacher, then you need to worry about it, too. But regular folks understand what you mean whether or not you use me or my. This is one of those cases where you might say it’s formal versus informal usage.

The possessive gerund isn’t always correct

In some cases, whether you use the possessive or objective form of the pronoun can affect the meaning of the sentence.

I love them singing.
I love their singing.

In the first sentence, it’s the action that’s being emphasized. I love it when they sing. The singing may or may not be good. I may love my daughter practicing piano┬ábecause I know that she’s going to get better some day, but for now, I tolerate it with cotton stuffed into my ears.

In the second sentence, it’s the thing that’s being emphasized. I love listening to the music.

There’s a great discussion thread here.

Image courtesy of Sira Anamwong at