I don't understand why she needs to stop dating him if she decides to be kickstart her career...
How Mai handled it in Aobuta was really great, they're not idols so what's even the problem there.
Just putting it into perspective
Yes, she has lost 11 times, but in more than 1000 years...
One was a demon that created the first magic specifically made to kill, the other one an elf (considering how rare they are probably another millenary elf maybe even before becoming Flamme disciple), and...
This spin is way too abrupt, first a timeskip out of nowhere, 2 chapters later she's going to make it big and now they're going to break up or something.
Way too fast, growth is not a rush
So when someone is close to death they become more able to see.
That's why ageing Grandmother is able to see them and hear them better now, as she's closer to her death. Might explain why this guy was also able to see them, he seems to be in poverty or something judging by his looks on the...