[He does wonder about her admission. After all, it is pretty clear she had spent some time getting dressed up a bit. But he'll go with the flow for the moment.]

Do I ever not look good? [Smug look goes here.] But yeah, let's get going before it gets worse.

[And he'll automatically move to her side, though he does move to where he's shielding her from the worst of the crowd and the road. As he glances at her, he finally notices the umbrella in her hands. Yes, he had been too busy looking at her to notice it.]

The weather did say it might rain, didn't it? I completely forgot about it, so it's a good thing you brought an umbrella. Though hopefully we won't need it.