I think the problem is that you are misunderstanding how your program moves through your file. $_ only changes when the outer while loop completes.

Consider this code:

while ( <DATA> ) {
    chomp;
    until( /[^\d]/ ) { print "$_"; }
}
__DATA__
1
A
B
C
[download]

This code will never terminate, it will just print '1' forever. The outer while block never completes and it never sees past the first line returned by the special DATA filehandle.

Try setting a flag to indicate what you should be looking for in your while loop. Use either an if-else chain or a dispatch table to handle each case.

I recently fixed this, I actually doubted perl taking in all of those lines. The code now looks like this

while(<>){    
    if (/^[0-9]+, |Sent:/){
        push (@logs, $_);
    }# elsif (/Sent:/) {
    #    push (@dates, $_);
    #}
}

print $logs[0];
print $logs[1];
#print @dates;
[download]

The Comments are there because I tried making it one statement, so as it goes through the file it now keeps the logs and dates together. The until statement was my problem, I guess learning from mistakes is always the best. Thanks for the help!