Haha, it is indeed less clear in the manhwa, if you want more detail, you can read the novel.
I won't go to deep about it but basically he's got his memories back from where it all started (which is the woman). The woman is basically asking if he wants to go to this other world (parallel world maybe? I'm not sure).
In his memories, he signed up a contract instead of getting an invitation, the contract is basically like a slave contract, but if you get an invitation, you get special privilege the higher the grade (bronze, silver, and gold). Learning from his memories, this time he didn't want to sign a contract. So the woman was surprised because he shouldn't know about the invitation or that world, that's why she ask if someone already approached him.
I think that's all I can explain, hope that helps
I only started on this like ch6 now and
this great n all but I'm kinda confused it went from him yelling about his money gone, had the memories back to him- and suddently weird woman and talk about some invitation contract and gambeling- Σ(  ̄□ ̄||)
plz explain thank you!