笑顔で、いや、寝付けなくてという僕の袖を、彼女が引いた。 > Who is smiling? Who can't sleep and what's the connection between smiling and problem with sleeping? The only clear part for me is that 'She pulled my sleeve'. Source: light novel. The context doesn't really have connection with this sentence, but after it he looks back at her and sees that she seems troubled by something.

>

I'm sure this sentence actually should have been

> **** ****

So it is the man that is having trouble sleeping. And for smiling, **it is highly likely the woman that is smiling** , because considering the and a comma after () in the sentence above, the clauses will be

> ( )

But the sentence looks like from some novel - there's some possibility that the man is smiling.