[General] Which one of you made a new friend the longest time ago?..

[Iryn_]

Hello!
If I want to ask a group of people about who made a new friend more close to today or more far from today, how do I ask?

Which one of you made a new friend the longest time ago?
Which one of you made a new friend the shortest time ago?

I bet these examples are wrong, so would mind giving me a hand?

 

[Rover_KE]

Which one of you made a new friend the longest time ago?:tick:
Which one of you made a new friend the shortest time ago?:-?
Which of you made a new friend most recently?:tick::tick:

`

 

[SoothingDave]

Who's gone the longest without making a new friend?

 

[Matthew Wai]

Is it correct to say 'Which of you made a new friend most long ago?'

 

[Rover_KE]

No.

 

[Iryn_]

Wow, I got one right :-D
Can I ask
Which of you made a new friend least recently?
as well?

 

[Rover_KE]

No.

 

[Matthew Wai]

Is 'most long ago' ungrammatical or unnatural?

 

[MikeNewYork]

I would say both.

 

[Matthew Wai]

Why is it ungrammatical to use the adverb 'most' to modify another adverb 'long'?

 

[Matthew Wai]

Can 'longest' be used an adverb modifying 'ago'?

 

[Roman55]

Why is it ungrammatical to use the adverb 'most' to modify another adverb 'long'?

I am not a teacher.

If it's incorrect usage and incorrect syntax it's ungrammatical by definition.