Here's what the author uses in his example: (from highline-1.5.0/examples)
#!/usr/local/bin/ruby -w
# asking_for_arrays.rb
#
# Created by James Edward Gray II on 2005-07-05.
# Copyright 2005 Gray Productions. All rights reserved.
require "rubygems"
require "highline/import"
require "pp"
grades = ask( "Enter test scores (or a blank line to quit):",
lambda { |ans| ans =~ /^-?\d+$/ ? Integer(ans) : ans} ) do |q|
q.gather = ""
end
say("Grades:")
pp grades
General documentation on HighLine::Question#gather
(from highline-1.5.0/lib/highline/question.rb)
# When set, the user will be prompted for multiple answers which will
# be collected into an Array or Hash and returned as the final answer.
#
# You can set _gather_ to an Integer to have an Array of exactly that
# many answers collected, or a String/Regexp to match an end input which
# will not be returned in the Array.
#
# Optionally _gather_ can be set to a Hash. In this case, the question
# will be asked once for each key and the answers will be returned in a
# Hash, mapped by key. The <tt>@key</tt> variable is set before each
# question is evaluated, so you can use it in your question.
#
attr_accessor :gather
These seem to be your main options w/in the library. Anything else, you'd have to do yourself.