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But, uh, Ross is a great guy. I was roommates with him in college.

That's from Friends episode [S06E21]. Shouldn't it be

we were roommates with him

Which sounds more natural?

3

When talking about a relationship we can in casual speech use a plural and say, for example "I was friends with him", or "I was roommates with him". These are possible:

Casual: Ross is a great guy. I was roommates with him in college.

More formal: Ross is a great guy. We were roommates in college.

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  • Are you a native speaker of British English? Please let me know if you see my comment. – GKK Mar 12 at 1:03
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No. You could say We were roommates, meaning you and him. But if you say We were roommates with him it unambiguously means "I and somebody else were roommates with him".

The original sentence may not make logical sense, but it is a perfectly normal way of saying it.

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  • 1
    "Friends with" is another example. "I was friends with him". – Eddie Kal Mar 8 at 18:29
  • Thank you both. That is very helpful. – tim afo Mar 9 at 18:42
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To complement the other answers, if using the first person past simple, I was, the most correct (formal) phrase would be:

Ross is a great guy. I was his roommate at college

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