I made a few changes:
1) it now works on my win98 system (no mail server at localhost)
2) To and From now include the people's names
3) fixed a typo

#!/usr/bin/perl
# just put this bad boy on your desktop and 
# double click as needed. :)

use strict;
use Mail::Sendmail;

# you
my $self = 'Monk';
my $email = 'me@workplace.com';

# her
my $chicks_name = 'Chick';
my $her_email   = 'chick@mail.com';

my @cheese = (
"hey $chicks_name\n\n I hope everythings going well today.\n I just wa
+nted to drop you a line.\n\nLove always,\n\t$self",
"Baby,\n I just wanted you to know how much I love you. You're great!\
+n\nLove,\n\t$self",
"I've been thinking about you all day. I can't wait to come home to yo
+u.\n talk to ya later,\n\t$self",
);

my @subjects = (
"hey babe...",
"a short message from your lover...",
"just wanted to say hi...",
"oh I love you...",
);

my %mail = ( 
To      => "$chicks_name<$her_email>",
From    => "$self<$email>",
smtp    => 'mail.your.isp',
Subject => $subjects[rand($#subjects)],
Message => $cheese[rand($#cheese)]
);

# $Mail::Sendmail::error gives details as to what went wrong
sendmail(%mail) or die $Mail::Sendmail::error;
[download]