Hello there. This indie drama was probably made around 2015-2018 and I originally watched it on Netflix. It follows a male bachelor in New York city who is a womanizer, and every chapter in the movie shows a title screen with a woman’s name, before proceeding to show the man dating and having sex with that particular woman. It is sort of a dark indie drama showing the loneliness of the bachelor life but also the lightness and freedom that the man experiences.
In the first scene, he is in a coffee shop breaking up with a woman who clearly has fallen for him. She is confused and doesn’t understand, but as the movie progresses we see the man only cares about being single and chasing new women.
There is also a funny scene in which he goes to a black woman’s apartment for a date and he brings he whiskey. And she complains like “why in the hell would you think I like whiskey.”
Unfortunately I can’t remember any of the actors names since it is indie. If i recall, the title may have had the word “night” in it, or “after dark”. But I’m not 100% certain.
A huge thanks in advance for all your help, I looked for this movie multiple times over the years and have had ZERO luck finding it.