True Left

"is there any notable romantic American counterculture works that you would recommend?"

My all-time (pun intended) favourite is Quantum Leap Season 2 Episode 22 "M.I.A." (+ additional context in Season 3 Episodes 1 & 2 "The Leap Home" and reprisal in Season 6 Episode 22 "Mirror Image"):

Beth Calavicci (Susan Diol) - Al's first wife and the only woman he ever truly loved. When Sam meets Beth during a Season 2 leap, she believes that she is widowed as her husband, who was serving in military action in the Vietnam war, had been reported missing in action and presumed dead. Al pressures Sam into stopping her forming a relationship with another man, insisting that "her husband" was still alive. Sam figures out Beth's identity and refuses to fulfill Al's request, deeming it to be selfish. In his next two leaps, Sam tries to save his own brother in the Vietnam war. This accidentally thwarts a rescue attempt that would have rescued Al, causing him to become a war prisoner. When Al is freed and returns home, he learns that Beth thought he was dead and had remarried, so he chooses to leave her alone. Sam is given a chance to put this right, and then assures Beth that her husband Al is alive and is trying to get back to her.

It is even more powerful if you watched the earlier episodes, because Al is initially introduced to us as an extreme womanizer (but otherwise heroic), so we come to understand that it is the above event which made him cynical. A key point which is missing from the above description is that Al could have told Sam about the potential side consequence before Sam took action during the Vietnam leap, but didn't. It is Sam's memory of this that made him determined to sacrifice himself to repay Al in the finale.