Cisheteronormative assumptions about women as able-bodied caregivers responsible for men’s sexual pleasure compound the stigma associated with chronic pain because of an assumed inability to fulfil gender roles in intimate relationships. There is a need to move beyond this deficit model of gender, chronic pain and intimacy. People of all gender identities live with chronic pain, forming fulfilling intimate relationships regardless of their condition(s). Starting from a strengths-based assumption that individuals living with chronic pain develop their own understanding of and pathways to intimacy, I conducted written interviews with thirteen people living with a range of pain and pain-related conditions to theorise gendered differences in understandings and experiences of intimacy in the context of dating. Findings show that intimacy is associated with vulnerability and authenticity. These connotations vary between men, women and gender diverse participants, aligning with gendered socialisation about intimacy and relationships. Men tend to prioritise physical intimacy. Women and gender diverse participants emphasise their obligation to perform the labour necessary for forming and maintaining connections. However, regardless of gender, experiencing intimacy requires implementing flexible approaches to dating because doing so makes closeness accessible.