I think the basic idea for the suggestion is fine.
There may be cases where the ruby user may prefer to not use (or depend) on a page
and may be fine with a long message output from --help. This may also depend on
the terminal and shell in use.
For example, I typically use bash + KDE konsole, and I rarely use any pagers at
all (very rarely I pipe towards "more" but I actually try to work in a way so
that I don't need any pager; I am more inclined to write some ruby script that
does re-format any output I may see).
On the other hand, when I use e. g. xterm, and say, perhaps the fish shell,
I may need to use a pager more often, simply because configuring (and using)
xterm is ... not so convenient.
So I think the gist of what I am trying to say is that it may be best to allow
the user to toggle the behaviour, possibly simplest just via a configure
option, and if anyone else needs more then a separate issue could be created.
So perhaps a --no-pager option, if the pager display becomes the default; or
vice versa if it is not the default. (Or perhaps an ENV variable, but this
is probably not really needed; just giving a few suggestions for that
possible case.)