In this chapter—"Are You Experienced? Life and Love in a Hookup Culture"— Orenstein breaks down the term "hookup." This refers to a casual encounter that may involve no more than kissing but that can consist of intercourse. Hookups are left intentionally vague, the details left up to those involved. Orenstein points out hookups are not a brand-new phenomenon. However, now teenagers live in hookup culture, where emotional and long-term connections are secondary to casual, physical encounters. In fact, most teenagers now see physical intimacy as a necessary precursor for emotional intimacy.

Orenstein deconstructs the notion that teenage boys are especially wired for hookups, particularly in relation to the constant messaging boys receive about emotional vulnerability and its supposed contradiction of masculinity. She cites a survey that "found our boys were as emotionally invested in their relationships as girls; perhaps having had less practice or support in sustaining intimacy, though, they were less confident in navigating them" (97). Many of the boys Orenstein spoke to said that they were not particularly fulfilled by their hookups, but that they knew no other way to engage with girls.

This chapter highlights the tension between power and vulnerability.