The difficulty with this layout, is that the dates are printed using a different grid from those of the comments, i.e., it makes a tabular environment an unsuitable way to typeset such a layout. In a way, the comments are typeset as "sideways-footnotes"!

To make it convenient for the author to enter the lines, we provide a user command as:
\adddate{date..}{Please ....}
We create a list to hold all the data. We then iterate through the list and typeset using two minipages. Adding a bit more salt and pepper and some LaTeX kernel black magic commands we get the minimal below:
\documentclass{article}
\makeatletter
\def\listone{}
\def\adddate#1#2{
\ifx\@empty\listone
\g@addto@macro{\listone}{#1}
\else \g@addto@macro{\listone}{,#1}
\fi
\expandafter\def\csname#1\endcsname{\footnotesize #2}
}
\parindent0pt
\begin{document}
% add some data
\adddate{date1}{1 Please use only dates obtained from the Center for Dates.}
\adddate{date2}{2 Please use original dates.}
\adddate{date3}{3 Please use original dates.}
% print the data
% define a macro for this for convenience
% if you want
\begin{minipage}[t]{2.5cm}
\@for\next:=\listone\do{%
\next \par
}
\end{minipage}
\begin{minipage}[t]{3cm}
\@for\next:=\listone\do{%
\@nameuse\next \par
}
\end{minipage}
\end{document}
You can add an additional macro to hold the code for the loops, if you are going to use such code extensively.