Was it your first time to talk to him?

Silverobama

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I was in an online chat group where people talk to each other using microphones, and I saw a friend of mine who hadn’t replied to my messages for a long time. I typed “Hey bro” in the comments section, but he still didn’t acknowledge me or show that he recognized me. Then I joined the conversation and asked the host "Was it your first time to talk to him?".

Is my question in italics natural?
 
I've got a feeling our AmE friends will say it's OK, and/or that "Was it your first time talking to him?" could also be used. (I'm sure they'll let me know if I'm wrong about that.) However, in BrE, we'd use "Was that the first time you had [ever] talked to him?"

I feel there's a lot missing from your story. It seems odd to me that you specifically told us it was a chat room where people speak using their microphones but you typed a message into the comments section instead. Why didn't you just join the spoken conversation and say hello to him?
How did the host know who you were talking about when you said "him"? Was your estranged friend still in the chat when you started talking to the host about him? If so, you would ask something like "Is this the first time you've talked to each other?"
 
I've got a feeling our AmE friends will say it's OK, and/or that "Was it your first time talking to him?" could also be used. (I'm sure they'll let me know if I'm wrong about that.)
You're right that "Was it your first time talking to him?" is natural and idiomatic in American English, at least in a somewhat informal register (it can be parsed as having an omitted "of" between "time" and "talking"); however, "Was it your first time to talk to him?" is very unnatural and would never be used.

I'd go so far as to call "Was it your first time to talk to him?" ungrammatical. If I'm right about the parsing of "Was it your first time talking to him?," the basis of the ungrammaticality of "Was it your first time to talk to him?" is that infinitive phrases do not work as objects of prepositions, even after the preposition has idiomatically gone missing.

Americans are, of course, perfectly comfortable with your British preference as an alternative. I'd probably opt for the "that"-clause instead of the "first time V-ing" construction in a more formal register.
 
I cannot argue with your ideas on AE, @Annabel Lee, but I have doubts about the two suggestions below:
You're right that "Was it your first time talking to him?" is natural and idiomatic in American English, at least in a somewhat informal register (it can be parsed as having an omitted "of" between "time" and "talking"); ...
I see no reason to magic up an 'omitted of'. Indeed, the construction with of sounds less natural to my British ears than that without. Perhaps it's natural in AmE.
... If I'm right about the parsing of "Was it your first time talking to him?," the basis of the ungrammaticality of "Was it your first time to talk to him?" is that infinitive phrases do not work as objects of prepositions, even after the preposition has idiomatically gone missing.
I find it hard to accept that a 'gone missing' preposition can have an effect on an infinitive phras.
 
I see no reason to magic up an 'omitted of'. Indeed, the construction with of sounds less natural to my British ears than that without. Perhaps it's natural in AmE.
I, too, find the version with of to be unnatural and do not use it. I didn't even want to type Was it your first time of talking to him? precisely because I find it unnatural. Nevertheless, that of-construction is out there.

As to why I'm inclined to posit an omitted of, it's simply because positing an omitted preposition makes the construction easy to parse and not very anomalous (some grammar-defying locution that Americans permit themselves).

Compare my first time talking with him with my first experience interacting with him: That was my first experience interacting with him. Of comes out of hiding in the paraphrase That was the first experience I had had of interacting with him.

Also, not to switch prepositions, but we have the spend time V-ing construction. I don't know how you're inclined to parse the grammatical relationship between time and V-ing in that construction, but many do so by positing an omitted in.
 
I, too, find the version with of to be unnatural and do not use it. I didn't even want to type Was it your first time of talking to him? precisely because I find it unnatural. Nevertheless, that of-construction is out there.
Out where?
As to why I'm inclined to posit an omitted of, it's simply because positing an omitted preposition makes the construction easy to parse
Easiness to parse is hardly justification for it.
and not very anomalous (some grammar-defying locution that Americans permit themselves).
I don't think that the fact that some Americans use it is, initelf, a reason to present a 'grammar-defying locution' as a grammatical explanation of another structure.
 
Out where?
Out in the wild, in published material in the English language. From Google Books:

"This was my first time of seeing stars and falling into a dark tunnel" (At First Light, by John Sikes, 2012).
"I even spoke with another surgical candidate, as we made a couple of stops together, explaining to him that since this was my second time of having open heart surgery I was at ease with the idea and knew what to expect" (The Second Time Around, by David Monseau, 2009).
"Very concise will be my accounts till I come again to relate my third time of being at Westminster Hall" (Diary and Letters of Madame D'Arblay, 1843)
Easiness to parse is hardly justification for it.
But when easiness to parse is put together with discoverability in actual usage and analogous constructions like "first experience V-ing" and "spend time V-ing," which can also be parsed as having an omitted preposition, there is indeed justification -- or at least enough justification to be worth mentioning as a possibly viable grammatical analysis.
I don't think that the fact that some Americans use it is, initelf, a reason to present a 'grammar-defying locution' as a grammatical explanation of another structure.
I have no idea (of) what you are saying.
 
in published material in the English language. From Google Books:
first time seeing people use drugs, first time borrowing thousands of dollars, … (The Naked Roommate by Harlan Cohen, 2005

... my first time working with an agency model , and my first time working with designer clothes. Inspiration in Photography by Brooke Shaden, 2014

If we wanted desperately to more members, we could probably both come up with hundreds of examples of our respective preferences. However, this merely shows that both form are used.
 
As to why I'm inclined to posit an omitted of, it's simply because positing an omitted preposition makes the construction easy to parse and not very anomalous

Yes, I see what you mean. Positing a missing preposition I agree helps make sense of things to some extent even though it's not there structurally. I imagine this 'of' may be a ghost of a former historical incarnation that has all but faded away, possibly a vestige from the pre-modern era of English and lingering on diachronically in places thereafter.

Compare my first time talking with him with my first experience interacting with him: That was my first experience interacting with him. Of comes out of hiding in the paraphrase That was the first experience I had had of interacting with him.

The -ing form, as opposed to an infinitive form, suggests a focus on a particular experience by the subject, which is why the word 'experience' works apparently synonymously with 'time' in many cases:

It was my first time driving a tractor.
It was my first experience driving a tractor.


Interestingly, however, with different structure, the mismatch in meaning is revealed.

It was the first time I had driven a tractor.
It was the first experience I had driven a tractor.

This tells me that the sense of there being a personal experience comes from the possessive word 'my' along with the present participle form of the complement participle clause. Also, that the word 'time' denotes the particular occasion at which the personal experience happens and that words that fit in this slot represent a small and closed class.

So an initial question that I would ask is what exactly this pattern is in its broadest but most precise formulation. At the moment I have it as this:

posessive determiner + restrictive modifier + 'time' + -ing clause

Additional questions:

Which other words can replace 'time'?
Must the pattern include a possessive determiner?
How large is the set of words that can fit in what I'm calling the 'restrictive' modifier slot?
Is the 'restrictive' modifier part crucial to the pattern? If so, how? Do we get a different pattern without it?
 
1. Was that the first time you have ever talked to him?
2. It was the first time I have driven a tractor.


Is it correct to use "have" after "was" as I have done?
 
Someone asked the following question on another forum:
This guy is talking about his experience of having been bitten by a dog, which happened two years ago. And he says now "It was the first time in my life I have ever been bitten by a dog". Do you like this use of the present perfect or would you prefer the past perfect, that is, "I had ever been...."?
A native speaker replied:
I would only use the "had" version on my deathbed where I knew that it was not possible for me to get bitten again before I died. Otherwise, that possibility remains and the use of "have" acknowledges that.
Does what the native speaker wrote ring true with anyone?
 
Not really - you can only experience something the first time once. It doesn't really matter if it ever happens again or not in terms of it being your first time.
 
It's simply a basic example of backshifting.

This is the first time I have ever been bitten by a dog.
That was the first time I had ever been bitten by a dog.
 

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