Ben and Jinx don't really go on 'dates' so I can't think of a singular instance, but they do go out often and do things that are basically dates, so i'll answer for that.

Jinx likes taking Ben to random ass places. Forests, abandon buildings, old subway passages, lakes, fields in the middle of bumfuck no where, that sorta thing. But they did that too as friends so I don't know if that counts LOL. More traditionally, if Jinx was feeling fancy he'd take Ben somewhere on the north side and find a kinda sketchy diner and eat with him there. Then take him to the alley and yk, do what Jinx does best.

For Ben, it'd be something more romantic. Dressing nice and eating somewhere then sitting together at a park and just talking about nothing, very tender. Or staying at home in bed and drinking while a movie plays on Jinx's laptop. He's a sap at heart hehe.