In the context of the story - which can be read in full online - the narrator, Jonathan, is describing the history of his relationship with his wife Saoirse. He describes her attractiveness (in some lascivious detail) and then mentions that he too was good-looking:
We got married when Saoirse was twenty-one and I was twenty-three. That seems impossibly young now but this was the late eighties. And we made a picture — I was a gorgeous kid myself. A Matt Dillon type, people used to say, which dates me.
He reminds the reader that they are now an older couple: born in the 1960s, married in the 1980s. The phrase "made a picture" means that they looked good together, good enough to be in a painting - a claim supported by her previously described beauty and his claim "I was a gorgeous kid myself". He compares himself at that age to the actor Matt Dillon, who, according to Wikipedia:
established himself as a teen idol by starring in the films My Bodyguard (1980), Little Darlings (1980), Tex (1982), Rumble Fish (1983), The Outsiders (1983) and The Flamingo Kid (1984).
At that time, Dillon was under twenty years old, and presumably very good-looking. But these films are from the early 1980s, which again reminds the reader that our narrator is no longer young and handsome. The phrase "which dates me" means that he's revealing his age.
But your dates can work out, and we were historically lucky in the property market.
He takes the "dates" idiom and runs with it, as this word has multiple meanings. In the previous sentence he was using it in the sense of "putting a date to", and given the context it might also put readers in mind of the sense of "romantic appointments", but now he's making it sound more like the sense of "points in history", which leads him on to the next part of his story: their "historic" luck in finding a home.
TL;DR: "made a picture" means they were pretty enough for a picture; "dates can work out" is a little piece of wordplay to link one part of his story to the next.