His universe earth-666 was erased by the antimonitor in crisis part 3 which means this is the third time he’s died and if you don’t believe me then look it up.
@Supernaturalpokemon Time moves much slower in Earth-666. An Interview Tom Ellis did confirmed its set in the 5 years BEFORE the show starts. Meaning he hasn't met Chloe yet. Meaning it's also BEFORE 2016 in-canon.