My Sorry Life(2021)

TV producer Kei and her recently retired comedian boyfriend Yoshi are working to conceive their first child as they consider marriage approaching mid-thirties—a process complicated by the fact that Kei has continued taking contraceptives. Annoyed by Yoshi relaxing into domestic life and slacking off at his part-time job, Kei has finally worked around her male colleagues’ obstruction to spearhead an innovative web series guest hosted by rotating everyday people. She invites Shiori, a young trans man working for her office’s delivery service and moonlighting as a bartender at an LGBTQ-inclusive space, to kick off the program. However, as Kei pushes forward, she reaches a breaking point.

Official site