It's not necessarily that it reflects poorly -- he knows plenty of people who have very few connections to speak of. He imagines that, unless something drastic in his life changes, he'll be one of those people at twenty nine, as well. However, most of the people he knows with no connections have something hidden in their pasts that they don't care to discuss. It doesn't necessarily speak ill of Ned's character, but perhaps of his experiences. He'd like to know about those experiences, but he knows better than to charge ahead with deeply personal questions without testing the waters, so to speak, as he's doing now.

Ned reads as though he's an open book, the kind of person who will answer questions honestly and guilelessly, but these are the easy questions, and nobody's truly an open book, not when it comes to certain matters. He's interested in seeing how much he can glean from Ned before that open book slams shut, so to speak.

He laughs at Ned's comment, watching as he begins cutting the strawberries. "Don't worry, I'm not the matchmaking type. You ever want to meet someone, though? The way I see it, you'd make a pretty good impression with the pies."