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I was proofreading some text for a friend and I stumbled across this sentence:

Glen, along with his close group of friends, took their first trip to Hawaii in 1986.

My question is this:

Is this correct, or should their first trip really be his first trip? I see the phrase between the commas as an nonessential phrase, and it appears to me that the sentence should be written so that it could stand alone without it. Therefore, to me it seems as though his first trip would be correct. However, the author is of the opinion that since there are multiple people going on the trip, their first trip is appropriate.

(My "real" answer would be to rewrite the sentence to avoid this issue in the first place, but I'm still curious.)

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    If it was the first time everyone in the party visited Hawaii, then there's nothing wrong with "their." If Glen's friends had visited the islands several times before, and it was Glen's first visit, then it should be changed to "his." – J.R. Jan 9 '14 at 18:24
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    @J.R. But if it was a first visit for all of them, I think I would have written it without the commas separating the subordinate clause and replaced 'along with' with 'and'. – WS2 Jan 9 '14 at 18:42
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    @J.R.: I don't think that should change the syntactical argument. – Cerberus_Reinstate_Monica Jan 9 '14 at 18:46
  • Perhaps change “close group of friends” to “group of close friends” also – James Waldby - jwpat7 Jan 9 '14 at 19:32
  • @Cerberus - You are correct; thanks for pointing that out. I'd be inclined to change the pronoun based on who was going there for the first time, but, as WS2 mentioned, I'd have to restructure the sentence to do that. – J.R. Jan 9 '14 at 22:12
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I think you are correct in this case, and that the author (who really ought to know better) is wrong.

Cecilia, along with the others, was wrong about Daisy's role in the fiasco at the game.

It, along with many others, was a dark and stormy night, and the rain fell in torrents, soaking Snoopy and Ms. L'Engle, who were soon to be among the great washed.

Glen and his friends took their first trip to Hawaii that year.

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"along with his close group of friends" is parenthetical, which means that, as you say, it is "nonessential", and removable. Take it out, and the sentence should make sense: "Glen took their first trip..." is, however, incorrect.

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