Never heard of this before I found it as part of a 4 film set on a Dollar Tree DVD.
It has a nice cast, but beware it's probably 95% Short and O'Toole, the others are just bit players. Reiser and Joanna Kerns play each of their best friends, with 80's underrated Goddess Corrine Bohrer as a neighbor. Lee Arenberg from the Pirates films plays a thief.
But basically it's the third date of these two leads, where both are hiding things that need to get sorted out. She smokes and has a kid, he just got fired and is broke.
I will say once all the drama hits, it does lose a little some of the fun it had…