1) This happened during a time where Riley was on an extended time mission. This means he was gone for months without word and presumed dead. Michael has a weakness for mourning girls, which was what Dinah was. So Michael offered to get her mind off of it.
2) Michael took Dinah to the Guggenheim. Dinah couldn't help but giggle at the goofy name but at least the pictures were pretty.
3) Dinah vetoed the idea of the fancy restaurant. They went for some New York style pizza. It was delicious.
4) Michael tried to get Dinah to relax, to get her mind off of Riley disappearing. It didn't work. The last hour of the date was him holding her on top of a Kord building as she cried.
5) There was no real chance of this happening again, not with Dinah as messed up as she was. So, in lieu of a "second date" their second time together was to make a small gold figurine of Riley, for Dinah to hold until Riley came back.
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