Yep, it's a fantastic friendship, and lots of fun to watch the interactions. We learn a lot about AIs from their conversations.
It's also great how Dale, Marigold, and Momo (and Faye, for that matter) have come to accept that May is very observant and insightful despite her foul mouth, and generally trust her advice and observations.
Somewhat the same for Pintsize -- in his rare serious moments, everyone seems to accept he actually knows what the hell he's talking about. As Claire said "He may be a horrible little robot, but he's not an asshole!".
One thing I love about the QC universe is that the AIs are genuinely bizarre in their own ways, with their own twisted senses of humor, and parts of their own personalities they don't understand themselves. A sentient being that really understood itself and did everything logically would be really, really boring, and wouldn't really fit in to human society very well at all. It might not even be truly sentient without some unpredictable "animal" component.