Although it's been quite a while since we initially read the section on Buddy Willard's hypocrisy being revealed to Esther for the first time, I am still stewing on exactly what signals were sent to Esther during this encounter. My initial reaction was that Buddy had almost slut shamed Esther early in the novel when he tells her she must "go out with a lot of boys" (Plath 59). This type of reaction to Esther's first kiss with Buddy seems like a situation familiar to a lot of young women today. Buddy, however, is not quite as rude but I think that this line does make Esther feel a little bad for how many guys she has gone out with, although according to her this is a reflection of her unpopularity with men rather than her sexual promiscuousness.
The discussion in class about how she felt betrayed by Buddy's exposure as a non-virgin made me think differently. Although Buddy did make her feel like the more experienced one of the two, she does not seem as bothered that he said earlier that she had gone out with a lot of boys, it was that he implied he hadn't gone out with a lot of girls. This raises the question of why exactly Esther would feel bad about the fact that Buddy in fact was more sexually experienced than she was. Simply enough, I think what frustrates her most is the fact that men are allowed to act innocent even though they are not, whereas if a woman was caught acting "innocent" in spite of being a non-virgin, she would be shamed. Additionally, Esther's frustration extends beyond just her interaction with Buddy. The lack of care by her schoolmates at a man's hypocrisy just goes to show her that there are institutions that she cannot topple herself, and the lack of emotion make her feel utterly alone.
On further reading, it is obvious that Buddy is really not a bad person, but one terribly swayed by society's gender expectations and norms (e.g. the scene where he tells Esther she will change her mind about children and marriage). However, I think it is interesting to note his tendencies to portray Esther as somewhat dirty, even if this is not the main reason she is upset with his hypocrisy (in addition to his questioning of who she will marry in the final chapter).
It is confusing, in some ways, that Esther denounces Buddy personally as a "hypocrite" (since he does admit his "affair" right away when asked, and seems pretty open in the way he talks about it with Esther). I think you're right that it's less his personal hypocrisy that bothers her (although the incongruity between his "golden boy" image and his seedy "affair" does chafe) but rather her discovery of a society-wide hypocrisy when it comes to issues of sexuality and gender. It's maybe not Buddy's "fault," but she sees how he takes advantage of the sexual double standard without a second thought, while she's suddenly all too aware that the same freedom is not permitted to her. It's one more way that she comes to view marriage and all the social conventions around it as detrimental to women, a profound limitation on their basic freedoms, in this case even before marriage itself.
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