A 45-year-old gay man living in a small city in the Midwest recently shared his experience with a casual sexual encounter that left him feeling uncomfortable and confused. During the encounter, he repeatedly had to clarify that he was not interested in anal sex, a boundary he had already communicated in his dating profile and during their conversation. He also mentioned that he did not ejaculate during the encounter, a situation he said happens about half the time with new partners and a quarter of the time when he masturbates. The man described that after the encounter, the other person became disinterested and quickly asked him to leave, then ignored him while he dressed. He noted that this was not the first time he had faced similar issues, but it was the first time he experienced such a strong negative reaction from someone else. Rich Juzwiak and Jessica Stoya, contributors to the How to Do It column, discussed the situation and suggested that the other person’s reaction might be due to personal issues unrelated to the encounter. They emphasized that the person’s behavior could stem from their own emotional or psychological state rather than the man’s actions. The contributors also mentioned that the man’s lack of ejaculation could be a medical condition, such as retrograde ejaculation, which can be caused by various health issues. They advised him to consult a doctor to explore this concern further. In response to the man’s question about better communication of boundaries, they suggested that if someone repeatedly misunderstands or ignores his limits, it may be best to leave the situation. They encouraged him to remain clear and direct about his preferences, as this is the most effective way to communicate his boundaries.