[lmkg]

Terminal prepositions are poor Latin, but they are perfectly acceptable English. The prejudice against terminal prepositions (and split infinitives, as well as such abominations as the s in island) came from a period in English linguistics where a bunch of grammarians thought that English wasn't dignified enough, and tried to pretend that it was a Romance language by shoehorning the language into awkward and ungainly shapes that faintly resemble Latin. The language of Shakespeare is dignified enough for me, without the groundless prescriptivist contortions. He, like many authors since then, has found that the natural aesthetic flow of English will sometimes (not always) result in the preposition most naturally falling at the end of a clause. When that situation arises, take the opportunity to celebrate the uniqueness of your native tongue.

[DanielBMarkham]

That was very eloquent, thanks for sharing.

I watched a series of college lectures on the history of language a couple of years ago, and that was one of the main points the lecturer made. Growing up in a traditional school system, I had never really thought about it that way.

Having said that, there is also a "high" and "low" version of most languages. The "high" version is full of obtuse rules and associated behaviors, while the "low" version is more catch-as-catch can.

So yes, you are correct: enjoy the art of your native tongue! I love screwing around with the rules. But also be aware that the culture you are in may prescribe all sorts of silly little rules, and knowing these -- and when to apply them -- can drastically affect other people's perception of your character. Whether we like that fact or not.

One of the things I wish I had more time for is the study of languages and the philosophy of languages. It has direct application in everything from AI to talking to Dolphins to programming projects. Really cool stuff.

[codebaobab]

Right. And just to drive the nail in a bit deeper: ending a sentence with a preposition is a grammatical construction that English gets from its roots as a Germanic language. German has what are called "separable verbs" where prepositions are combined with verb roots to create a new verb. In certain cases, the preposition prefix is split off of the verb and placed at the end of the sentence. The preposition must come at the end of the sentence in order to be grammatical. You can see remnants of separable verbs in English:

"I passed the man in the red hat by." pass-by

"I threw all of my old, useless papers out." throw-out

To repeat the parent's point: the stricture against ending a sentence with a preposition is simply a bias for grammatical structures that English inherited from Latin (through French) and against structures inherited from German.

The rule against splitting infinitives falls into the same category. It is not possible to split an infinitive in Latin because infinitives aren't made up to two words.

Again, these two rules (and others like them) are about biases, not about grammatical correctness or even clarity of communication. When you say "Who am I speaking with?" and "To boldly go where no man has gone before.", no one is actually left scratching their heads and thinking "I wonder what he means?"

[colanderman]

I would never say either of those sentences.

"I passed by the man in the red hat."

"I threw out all of my old, useless papers."

Both of those not only keep the preposition away from the end of the sentence and keep it near the verb to which it belongs, but most importantly they sound more natural.

Your example of "Who am I speaking with?" follows this same pattern -- "with" is kept next to the verb "speaking".

[imperialWicket]

Valid points, noted. I did mention that you should avoid the closing preposition, and you are right to acknowledge that there are cases where it is acceptable. However, I think it is safe to assert that most of the time, it is simply imprecise speech.

If "With whom am I speaking?" sounds snooty, then I guess I am a snob.