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Can your first sexual experience happen without ever physically touching another person? In Digital Firsts, we explores how technology is reshaping sex, intimacy, relationships and even what we mean by a “first time.” MaryJane is joined by Dr. Markie Twist and Dr. Neil McArthur, the scholars who introduced the concept of digisexuality, to unpack the increasingly blurred lines between human sexuality and technology. From sexting, online pornography and video intimacy to virtual reality, AI companions and human-like sex robots, we ask: When does a digital sexual experience become significant enough to count as a first? Can intimacy with an AI feel emotionally real? Can a relationship with an AI companion constitute cheating? And could technology become not just a tool for sexual connection, but an important part of someone’s sexual identity? The conversation also explores digital consent and vulnerability, relationship boundaries, stigma surrounding digital relationships, and what emotionally responsive AI could mean for future generations growing up with technology as a companion rather than simply a tool. As intimacy becomes increasingly digital, perhaps the bigger question isn’t whether these experiences are “real”, but who gets to decide what counts as intimacy in the first place?