In 2364, Data was infected with the Psi-2000 virus by Tasha Yar, the chief of security. Data was sent to get her from her quarters and became infected, after which he became intimate with her while they were both under the influence of the virus. Later on, in a tragic accident, Tasha was killed by Armus, who was an incarnation of pure evil. Data still keeps a hologram of Tasha, which is one of his most prized possessions. Later on, Data dated a crewmember named Jenna D'Sora.
Data read all material available on the subject of dating and marriage.
He created a special subroutine in his programming, especially for Jenna. Once, when Jenna asked Data what he was thinking about when he kissed her, he responded that he was reconfiguring the warp field parameters, analyzing the works of Charles Dickens, calculating the maximum amount of pressure he should apply to her lips, considering a new food supplement for his cat, Spot, and more. Jenna broke up with Data sometime later because she felt that he would not be able to be responsive to her needs since he was incapable of experiencing emotions. He was even tempted by her offer to make him fully human, but only for 0.68 seconds.