You can find the movie streaming on platforms like Lifetime Movie Club or available for rent/purchase on Apple TV and Fandango at Home . 3 Holiday Tails (TV Movie 2011) - IMDb

Lisa’s neighbors, a recently retired couple, act as the story's architects. Realizing that David and Lisa are still "meant to be," they use their golden retriever, Jake, and Lisa's three puppies to orchestrate "accidental" meetings between the exes.

The film avoids heavy drama or tragedy, focusing instead on realistic internal conflicts like trust issues and the fear of moving out of one's "comfort zone".