Jake actually does end up responding well to Dirk's advances through pesterlogs, once he realizes that he's definitely talking to the real person and it's not all some baffling jape at his expense.

But as soon as they meet in person he backs off completely, and Dirk has no idea why.

It turns out that when he's around Dirk in the flesh all he can see is his resemblance to the robot that beat the crap out of him regularly. And it turns out that's just not something he can get past (or, if he can, not until several years have passed and Dirk's grown out of the resemblance some).