Definition
English idiom – “can’t win with (someone)”
This idiom is used to express frustration at being unable to please someone no matter what effort is made.
“When I offer to help, he gets annoyed. When I don’t, he complains. I really can’t win with him.”
Clip 1
Friends – Season 2 Episode 5 (1995)
In Friends Season 2, Episode 5 Ross says, “It’s like we can’t win with you guys” during an argument about money. Earlier in the episode, Rachel, Phoebe, and Joey complain about not being able to afford expensive activities, including a dinner and concert tickets. In response, Ross, Monica, and Chandler decide to pay for the tickets themselves, thinking this would solve the problem. However, instead of feeling relieved, the others are offended and feel patronised for being treated differently. Ross’s line reflects his frustration that their attempt to accommodate the group still leads to criticism and is why he uses this idiom.
Clip 2
This is 40 – (2012)
In this scene from This is 40, Pete (Paul Rudd) says, “I can’t win with you” to his wife, Debbie (Leslie Mann), during a heated argument. The context is that Debbie feels Pete is emotionally distant and not fully present in their relationship. Pete, frustrated by this accusation, responds by expressing his frustration that no matter what he does, it’s never enough for Debbie. He feels criticised and misunderstood, which leads him to make this remark about not being able to “win” in the situation. The scene captures the tension and communication breakdown in their marriage.
Clip 3
Fight Club – (1999)
In Fight Club, Marla says, “I just can’t win with you, can I?” to the Narrator (played by Edward Norton) because of his strange and confusing behavior. He has two personalities: his mild-mannered, insecure self and his chaotic alter ego, Tyler Durden. Marla is frustrated because she can’t connect with him or understand which version of him she is dealing with. No matter how she tries to engage with him, she feels like she’s constantly failing to get through, which leads her to express her exasperation using this phrase. The duality of his character makes communication and their relationship difficult.
Clip 4
Paul (2011)
Graeme (Simon Pegg) is accidentally shot but is healed by Paul, the alien. A man nearby falsely claims that God revived Graeme, and the people around them believe this story instead of the truth. Ruth (Kristen Wiig), frustrated by how easily people believes this, says to Graeme, “You can’t win with these people.” The phrase reflects her exasperation at the situation, where people will choose to believe God saved Graeme instead of Paul.