I'd got out with him and talk about it....if they happened within the last couple of years i think id have 1 date only. If they were a long time ago...i might try him out.
As more questions to clarify....if they're recent, I'd won't go further.
TBH, I don't think I could be okay with more than one DUI, regardless of the time between them. I think once is a huge mistake and you should learn from it.