I never thought to ship anyone from this show before, well, besides Marge and Homer, mostly I just watch it for the humor. But, yeah, I could see this ship working.
I was thinking about this again. I wonder if Lisa would be jealous if Milhouse took an interest in a girl who was similar to her. It's like the old saying, "you don't know what you've got 'til it's gone".
And it doesn't have to be immediate. How many seasons between the time Nelson "changed" for Lisa when they were dating to the current Nelson? Probably more than a couple.