A Gift Wrapped Christmas (2015) on Netflix

Plot summary

Gwen Burke spends her working days at Giftwrapped, matching clients with gifts chosen for the person who will receive them. With her colleague Anna on maternity leave, she inherits the agency's most valuable account: Charlie Baker, an executive at Vistasun Equities. Charlie buys without thought and keeps to plain dark suits, and he leaves his eight-year-old son, Owen, largely alone while he works. Gwen meets the boy on a delivery and decides to loosen Charlie up for the holidays. Her own plans shift when the sister she lives with, pregnant, needs the room for her growing family. Charlie's business associate Victoria Dane expects to marry him. Gwen sets out to give Charlie and Owen a Christmas together.