Hello, my name is ***** ***** I will be the immigration attorney helping you today.
His debt should have no bearing on whether he is allowed into the US or not. Whether Japan will allow him to leave is something different and I cannot speak to that because I am not an expert in Japanese law. But I can tell you that someone with debt can still come on an ESTA to the US.
Yes, he should be able to come to the US then go back after being married.
I know immigration issues like these sometimes seem complicated and confusing. If at any time you would like to have a more detailed consultation by phone or if you need help with preparation or review of applications, I can send you an offer to exchange contact information so I may help you with these legal services for a reasonable fee. You don't have to decide if you would like that now, but just letting you know it's an affordable option for you to keep in mind for whenever you'd like.
Good luck to you and I hope this answer has helped you!
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