The Two Jews on Christmas session refers to a recording session that occured on 2001-12-25 at Antenna Studios in New York, NY which resulted in the recording of seventeen songs: twelve of which eventually released on the LP Songs, which was self-released in early 2002, as well as five additional songs that are currently unaccounted for.

The back of the Songs CD cover notes: "Songs, recorded on December 25, 2001. Times Square was cold, quiet, abandoned. Joe Mendelson and I were going to archive a list of songs. We recorded seventeen – here are twelve of them. When you are listening to this little disk, try to think that you are in on a secret…”

Regina also made reference to the recording session on her personal website. On 2002-12-22, Regina posted, " i am wishing you all a wonderful new year, and a happy christmas... i am going to my 2nd annual "two jews on christmas session" with Joe Mendelson... see you choo-choo, reginka"

In interviews, Regina has referred to the Two Jews on Christmas session as a demo recording session that happened to turn into an album release. While twelve of the seventeen songs are known due to their eventual release on Songs, the remaining five can only be speculated. It is possible that some of the songs currently associated with the Two Jews on Christmas (Again) sessions, are actually part of this first session. While these demos did find their way to the Internet, it can only be speculated which demos were recorded during which sessions.