How do I calculate a String's width in Ruby?

You should use the RMagick gem to render a "Draw" object using the font you want (you can load .ttf files and such)

The code would look something like this:

   the_text = "TheTextYouWantTheWidthOf"
   label = Draw.new
   label.font = "Vera" #you can also specify a file name... check the rmagick docs to be sure
   label.text_antialias(true)
   label.font_style=Magick::NormalStyle
   label.font_weight=Magick::BoldWeight
   label.gravity=Magick::CenterGravity
   label.text(0,0,the_text)
   metrics = label.get_type_metrics(the_text)
   width = metrics.width
   height = metrics.height

You can see it in action in my button maker here: http://risingcode.com/button/everybodywangchungtonite

Use the ttfunk gem to read the metrics from the font file. You can then get the width of a string of text in em. Here's my pull request to get this example added to the gem.

require 'rubygems'
require 'ttfunk'
require 'valuable'
# Everything you never wanted to know about glyphs:
# http://chanae.walon.org/pub/ttf/ttf_glyphs.htm

# this code is a substantial reworking of:
# https://github.com/prawnpdf/ttfunk/blob/master/examples/metrics.rb

class Font
  attr_reader :file

  def initialize(path_to_file)
    @file = TTFunk::File.open(path_to_file)
  end

  def width_of( string )
    string.split('').map{|char| character_width( char )}.inject{|sum, x| sum + x}
  end

  def character_width( character )
    width_in_units = ( horizontal_metrics.for( glyph_id( character )).advance_width )
    width_in_units.to_f / units_per_em
  end

  def units_per_em
    @u_per_em ||= file.header.units_per_em
  end

  def horizontal_metrics
    @hm = file.horizontal_metrics
  end

  def glyph_id(character)
    character_code = character.unpack("U*").first
    file.cmap.unicode.first[character_code]
  end
end

Here it is in action:

>> din = Font.new("#{File.dirname(__FILE__)}/../../fonts/DIN/DINPro-Light.ttf")
>> din.width_of("Hypertension")
=> 5.832
# which is correct! Hypertension in that font takes up about 5.832 em! It's over by maybe ... 0.015.

You could attempt to create a standarized "width proportion table" to calculate an aproximation, basically you need to store the width of each character and then traverse the string adding up the widths.

I found this table here:

Left, Width, Advance values for ArialBD16 'c' through 'm'
Letter  Left    Width   Advance
c        1       7       9
d        1       8       10
e        1       8       9
f        0       6       5
g        0       9       10
h        1       8       10
i        1       2       4
j       -1       4       4
k        1       8       9
l        1       2       4
m        1       12      14

If you want to get serious, I'd start by looking at webkit, gecko, and OO.org, but I guess the algorithms for kerning and size calculation are not trivial.