as i understand a router connects different networks (one network per interface). if the asa was on a different network due to the mask being wrong and it was the inside lan interface he would not be able to ping it at all even if the DG was pointing to the router.
I could be wrong tho and learn different as a advance further into networking.
i'm pretty sure it could be possible given the right scenario.
suppose the PC is 1.2/30, the router is 1.1/24, and the ASA is 1.10/24
the router and ASA can obviously talk to each other no problem.
the PC and the router can also talk to each other no problem.
when the PC would talk to the ASA, it wouldn't know how to get there since it's not a directly connected subnet (from the PC's perspective). so, it would send the packet to the router, which would then forward it to the ASA.
to respond, the ASA thinks the PC is in it's directly connected subnet, and will simply ARP for 1.2. the PC (i'm assuming at this point) would respond, but would send its response again thru the router. Once the ASA has the MAC of the PC, it will simply send the response directly to the PC.
it's definitely asymmetric, but it could work that way.
however, he's already said the subnets are configured as /24, so this isn't the problem. (damn, thought i was on to something)