Dealbreaker: He Has Low Self-Esteem

This article is pretty interesting. We follow a feminist author who engages in a months-long text-relationship with a man with low self-esteem (lack of employment enables him not to "feel like a man"). The author explains her mixed feelings- the feminist in her wanted to liberate him from his own problematic gender expectations while she allowed him to manipulate her emotional investment. To rub salt into the wound, he ends up meeting another woman! I'd like to know more about this other woman and why she "won" (although, this guy doesn't seem like much of a prize). Was she far less successful than he was? Was she just unsuccessful enough to make him "feel like a man"? Did she enable his "identity crisis" more than the author? The reason why this interests me so much is because if a successful woman makes this guy feel emasculated, what in particular does not emasculate him? That in itself, I'm sure, is entirely problematic and in need of some serious unpacking.