As far as I know, you can't in the first year due to him leaving Tuesday and being unavailable all of Wednesday. However, I never tried to woo Lloyd so there may be some secret trick to asking him but I wouldn't hold my breath.
Yeah, it's been discussed before (I am also a Lloyd fan...). The only theory that was come up with at the time was that if you were somehow able to get a storm on Tuesday (possibly Monday as well) so Lloyd would stay home from work, then maybe you could ask him. But nobody that I know of has been able to get bad weather on that day yet to try it out.