Hey Nox,
We started one night purely by accident, I was out and running late, and couldn't get home by 7. DH just did her normal bedtime routine, and gave her her sippy cup with milk in it, and it worked! She was in bed asleep when I got home at 7:15! We just kept doing it. It didn't matter at all that I was there on subsequent nights, and now it doesn't matter whether its me or DH that gives her her "ilk", although I try to get DH to always do it so he feels more important She settles so well for DH now, much more easily than for me... She had always had a sippy cup that we used for water and small amounts of cows milk, so she was used to the cup aspect of it. She only drinks about 40ml of milk from the cup at a time, sometimes less.

Maybe you need to go out one night, and just see what happens if DS is left alone with your DH, and see how he copes? I was actually at the hairdressers when it worked for us.. Give that a try maybe?!

good luck..