I've driven the 07 Fit in Auto and the 09 in Auto and Manual. The 09 is a spectacular vehicle. They fixed all the issues had with the previous generation including the A-Pillar blind spot. They lengthened, and widened it by a few inches, which mean a world of difference if you're a backseat passenger. Quality all around, and much more attractive then the xd in my opinion. You can pass on to your boyfriend if he hasn't tested out the manual, that it's a solid shift, no sloppiness, with a good feel to the clutch (as opposed to, say a Dodge Neon for example- blech)
The seats are made of much better material and more comfortable to sit in- the active head restraints are a plus as well. I can't say I'm an enormous fan of the head unit radio design- it could be a pricy bezel ir one wanted to replace it with an aftermarket one in years to come. That's honestly my only gripe.
I would have bought a Fit hands down if I didn't want a minivan more. (I went for an Odyssey- I'm 21 and really weird lol)