How to keep description label together with first element of multiple nested environments?

Question

I have this setup:

\documentclass{article}

\begin{document}

\begin{description}
  \item [Heading]~
  \begin{quote}
    \begin{enumerate}
      \item First
      \item Second
    \end{enumerate}
  \end{quote}
\end{description}

\end{document}

I know of the samepage package but that seems not to help since I cannot easily split up the enumerate's first item to put it together in a samepage.

Also, I do not like the needspace approach since, if I understood it correctly, I would need to know how long my First enumerate item is. But I don't want to set that manually.

Is there a way to tell LaTeX just to keep the Heading and First item together?

Edit

Here is some illustration.

This should not happen:

Heading
---- new page ----
    1. First
    2. Second

If there is enough space below the heading, then this would be fine:

Heading
    1. First
---- new page ----
    2. Second

Otherwise

---- new page ----
Heading
    1. First
    2. Second

Also, I guess it makes sense that part of the first item might be on the first page and part on the second, if first item goes over several lines.

Heading
    1. First First First First First First 
       First First First First First First
---- new page ----
       First First First First First First 
       First First First First First First
    2. Second