Nice capture of the moment. The expression give off by the eyes and the mood is really great with the photo title!
The idea of street portrait is in the mood and the feel of that moment rather than common photography skill. Something, the moment is very short and you might just miss it and that's it (Example is a glimpse of a person turning their head). When it is long, adjustment to lighting and composure can be done (Example is an old couple sitting on the bench and resting).
From my POV, TS did good in photo 1 where if TS try to move to the front and do a shot, the expression and chance might have been gone. Do the first shot and see if there is a chance for another.