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Are the sentences like the ones below grammatical?

  • 1) He's somebody I hate the personality of.

  • 2) It's a song I hate the lyrics of.

  • 3) She can't date someone she doesn't like the appearance of.

  • 4) She is a beautiful girl I hate the pictures of.

Description: In the first one, I am giving my opinion on somebody by saying that I hate his personality.

In the second one, I'm giving my opinion on a song by saying that I hate the lyrics of that song.

In the third one, I'm saying that she cannot date a person if she doesn't like his appearance.

In the forth one, I'm saying that she is beautiful but I hate pictures of her.

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Yes, all are grammatical, although there is some debate whether it is OK to end a sentence with a preposition like "of". Some people object to it, while other think it's perfectly acceptable.

There are more "graceful" ways to express all your sentences using "whose":

He's somebody whose personality I hate.

It's a song whose lyrics I hate.

She can't date someone whose appearance she doesn't like.

She's a beautiful girl whose pictures I (nevertheless) hate.

Note that it's normally fine to use "whose" for non-person things like "songs", if only because English doesn't have an appropriate pronoun for that situation. More information.

If you also find this use of "whose" inelegant, the alternate phrasing "of which" is a common substitute:

It's a song the lyrics of which I hate.

  • Thank you for your answer. The structure in the sentences you gave is used less commonly than the structure I gave that ends with "of", right? – Fire and Ice Oct 30 '18 at 20:11
  • @FireandIce No. I would not personally write using that structure, as the alternatives sound better. – Andrew Oct 31 '18 at 5:01
  • Thanks again. Do you think those sentences I gave are awkward like Lambie does? – Fire and Ice Oct 31 '18 at 7:23
  • @FireandIce yes, they are awkward. As I said, I would not personally write them, as there are other, more "elegant" phrasings. – Andrew Oct 31 '18 at 14:36
  • You say you wouldn't write them. Can you ever say them? – Fire and Ice Oct 31 '18 at 14:42
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It's Ok to end a sentence with of but most of those sentences are all awkward as they are really about possessives and not verbs followed by OF and a noun. We tend to find less awkward ways to avoid of which,by which or whose, etc.

For example: That's not someone I've heard of.

[to hear of something or someone]. There, the of would be used.

1) He's somebody I like the personality of.

That would be generally phrased something like this: He's one person with a personality I like. [thereby avoiding whose].

When one likes (hate, dislike, love) something or someone, that is a direct object. There is no of. Also, English likes possessives: I like that man's personality. or: He has a personality I like. That's man's personality is something I really dislike.

That said, more sophisticated speakers often do say things like:

He's someone whose personality I like.

These speakers do not necessarily avoid of which, whose, etc. all the time as colloquial speakers would.

That sentence makes sense if discussing personalities. A more natural rendition of it would be: People like that have personalities I like.

2) It's a song I hate the lyrics of. [same as above, there is no need for of]. That's a song with lyrics I hate. [with, as in 1), avoids of which or whose].

3) She can't date someone she doesn't like the appearance of. [this one works better because there is: like or not like **the appearance of a person though we generally say: a person's appearance]

Generally speaking, it is the verb followed by OF + a noun that will trigger a non-awkward final of:

  • There really was no matter to speak of. [to speak of a matter as in to discuss]

In most other cases, look at your implied possessive: the personality of the man, [the man's personality]; the lyrics of the song, [the song's lyrics]; the appearance of a person (a person's appearance); pictures of the girl, the girl's pictures.

  • She can't date guys with personalities she dislikes.
  • They dislike songs with lyrics like that or those types of song lyrics.

Mostly, in the numbered sentences, there is no need for a final of with these verbs. Native speakers avoid those hidden possessives by using a possessive or by using a construction with "with" or some other construction in construction with like, dislike, etc. unless it's a preposition + noun.

We have nothing to talk about. [talk about something]

  • Thank you. Does every native speaker think they are awkward like you do? I mean, wouldn't any native speakers say the sentences I gave? – Fire and Ice Oct 31 '18 at 7:59
  • @Fireandice Do you seriously think I would waste my time with this if I didn't think most native speakers would agree? Most native speakers would go for Andrew's standard grammar use of whose over any final of such as you have provided. Those particular of's were so odd, I set about coming up with most likely reason for why that is...And he has said the same thing asI did: "I would not personally write using that structure." And now you can see why. – Lambie Oct 31 '18 at 14:02
  • Thank you for trying to help. It looks like you are rebuking me by the way. Also Andrew said they are grammatical. – Fire and Ice Oct 31 '18 at 14:13
  • The fact that you spend a lot of time answering doesn't give you the right to be rude. Please don't answer any of my questions. – Fire and Ice Oct 31 '18 at 14:20
  • @FireandIce Being grammatical or is not the main issue here. That's why I did not answer the question directly. And I did say that 3) is the only one that might spring up spontaneously in conversation, as far as I'm concerned. You repose the question in your comment and you play one answer off against the other. And this is not the first time you have done this. I asked you a question in my first comment above! How is that rude? – Lambie Oct 31 '18 at 14:25

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