Tonight's TNG was "Data's Day." There's a scene where Data asks the holodeck to conjure up a dance partner, and I don't think it's a coincidence that she looks like Denise Crosby's Tasha Yar.
Given what Data says in about his relationship with her in "Measure of a Man" it seems to have gone deeper than his one night with her in "The Naked Now." I do believe he got closer to her right up until she died.
One thing I really think should have happened in Season 1 of Picard was not that Picard was waiting for Data when he dies, but Tasha.