Great Minds with Dan Harmon (2016)

S2E12 Too Many Girls, Not Enough Aiden

Aiden finds himself caught in a tight spot with Madison, Kyla, Ashley, and Spencer, each tugging at him over their friendship and romantic dilemmas. It becomes clear that to please one of them, he risks shattering someone else's feelings, leaving him torn and struggling to navigate the tangled web of their expectations.