Interesting link.
My analogy was different from your case b/c the lone pair...wait, I mean LONE PAIR...was on a negatively charged carbon rather than a neutral nitrogen.
This does make a difference. For pyrrole, most of its resonance structures have a negative charge on carbon, positive charge on nitrogen. According to your link, the dipole vector points away from nitrogen.
For pyrrolidine, there are no resonance structures. The only effect on dipole is the inductive effect (electronegativity of the nitrogen). As such, the dipole vector points toward the nitrogen.
If the vectors are pointing in opposite directions, though, I don't see any simple way of predicting the relative sizes of the dipole moments. I had imagined the vectors pointing in the same direction...toward the nitrogen due to electronegativity, but with a smaller dipole moment for the delocalized system.
Btw, I find give/take snacks lame. Just ask for clarification or tell me if you find me unhelpful and I will stop trying.