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As she tries to decode the laws of attraction and commitment, Chelsea turns to an old flame, a Vegas wedding guru, and the founder of Ashley Madison.

Chelsea confronts her own issues with technology in a trip to Silicon Valley to pitch an app, code with kids and dissect tech's effect on our brains.

Chelsea probes America's racial tensions by visiting a former plantation, meeting Al Sharpton, and facing critics who condemn her use of stereotypes.

To explore the power of drugs, Chelsea smokes up with Willie Nelson, hears addicts' horror stories and travels to Peru to try a potent hallucinogen.