DC 1 - have left him twice overnight, once with MIL for our 10th anniversary when he was 18 months and once with my dad when I was in labour with DC2 when he was 2
DC2 is 2 and haven't left him.
I would love a night away with DH but we don't have anyone to have them. My ILs live abroad and my parents couldn't handle both kids very easily ( and also haven't offered). We have friends who probably would if we asked but they don't know the kids well enough for us to feel comfortable