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I'm not sure if I could use "only" in this sentence: "Upon their only two encounters, he managed to leave a good impression on her." I'm trying to emphasize the point that they met only twice. Also, I was wondering if "upon" fits in the context. The idea is that he performed well during both of the meetings, and she was impressed by his overall performance. Thanks for your help :)

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Yes, you could use that construction, and it is grammatically correct; but it is an odd use of "upon", since that is almost always used to refer to one specific incident or point in time.

It would be much more idiomatic (common) to phrase this as;

  • "{in/after} only two encounters,..." (emphasizes that the combined effect of two encounters was a good impression) or
  • "In {each/both} of their two encounters.." (emphasizes that each time he made a good impression)

Trying to emphasize both at once is a bit more involved, and would sound awkward: "In each of their two encounters, and taken as a whole..." "In each of their two encounters, as well as cumulatively,..." Whatever small nuance this might add is not, IMHO, worth the clumsiness.

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Both only and upon don't quite work as you use them.

We mostly use only in conjunction with a verb such as are or have

How many biscuits are left?

We only have two.

or

There are only two

So we might say

They only had two encounters but he managed to leave a good impression on her.

We can use only slightly differently

How often have you met Jim?

Only twice (or only three times)

Here we are removing the verb, it's short for

I only met Jim twice

So in this style we could say

They met only twice but he managed to make a good impression.

or

They only met twice but he managed to make a good impression.

I prefer the former as the only twice seems to emphasise the small number.

The "on her" while correct feels a little over precise, so I omit it.

Upon is usually used for a single event

Upon reaching the summit they sat down to rest

Upon meeting they shook hands.

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    "We mostly use only in conjunction with a verb such as are or have." Are you quite certain? I'm not!
    – anongoodnurse
    Commented Mar 12, 2015 at 7:24
  • medica, in the examples I can think of the verb is sometimes elided but I think it's usually there implicitly or explicitly. Please give a counter example? Happy to fix it if I'm wrong.
    – djna
    Commented Mar 12, 2015 at 7:29
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    I can only think of several examples... After only two months, she could read... Only five more classes, then he could could leave forever... He lived only to make others happy... She only sang at noon... etc. etc. (?)
    – anongoodnurse
    Commented Mar 12, 2015 at 7:38
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    Ohm I thought you were saying only was used with those two verbs! Yes, I agree OP's sentence sounds odd, but I think it's the way it's constructed.
    – anongoodnurse
    Commented Mar 12, 2015 at 9:27
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    I don't think there's anything inherently unusual or "questionable" in usages such as his only two remaining {whatever it is he's only got two of left}. I agree OP's "temporal" use of upon is non-idiomatic, but I'm not convinced it's to do with there being multiple encounters. It would still invariably be on even if there had only been one prior encounter.
    – FumbleFingers
    Commented Mar 12, 2015 at 14:04

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