grammar school

I ran into my dear neighbor Jean this afternoon. She asked about my workout journey and I told her that I had injured my back, so it was on “hold”. She was going to ask if I would join her for a Pilates workout, but then she said:

So, my asking you to come along is pointless.

After we laughed, she issued me a challenge. She asked me how to describe the grammar of that sentence so that she could find it online to show her students, because she has heard them express the above thought in this way:

So, me asking you to come along is pointless.

I accepted the challenge and I went back to my computer, and here is the answer I came up with:

“asking” is the gerund (I got that name right!) and “My asking you to go” is the gerund phrase which is the dependent or subordinate clause acting as a noun and in fact the subject of your sentence. “My” is a modifier to “asking” within the phrase.

From grammar.about.com, search on possessives before gerunds:

Possessives Before Gerunds
“In your writing, when a pronoun appears before a gerund (an -ing verbal used as a noun), use the possessive case. We have tasted their cooking. In this example, cooking is used as a noun and is the direct object of have tasted. If a pronoun appears before a participle, use the objective case. We have watched them cooking. In this second example, cooking is used as a participle to describe them.”
(Robert DiYanni and Pat C. Hoy, The Scribner Handbook for Writers, 3rd ed. Allyn and Bacon, 2001)

So in your sentence, it should be “my” because the subject of the subordinate phrase “My asking you to come along” is “asking” and the “my” is modifying the “asking”. According to the explaination I just included above from grammar.about.com, if you use “me”, you are saying that the subject of the phrase “me asking you to come along” is “me” and that the “asking” is modifying the “me”. Think about the meaning you are trying to convey by using the whole phrase as the subject of the larger sentence and that is where you get your answer. The main idea (subject) of the phrase which is representing the noun in the larger sentence (My asking you to come along is pointless.) is “asking”, not “My/me”.

Neighbor Jean answered right away:
I am so darned impressed!
Thanks–jean