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J-1 visa overstayed for 5 months while also holding B-2 visa. Possible to return to US under new B-2 visa?

PLEASE READ THE TEXT as I feel that it is a complicated issue for me!!

CONTEXT: I went through an intern course lasting 1 year from July 2017 to July 2018 with the J-1 visa but unfortunately, I was terminated halfway through the course by my host company due to disciplinary actions (I was late once during my probation and the next two same infractions happened during the last month I worked). However, my sponsors changed my SEVIS to an authorized early withdrawal, saying that my course is shortened instead and my 30 day grace period started when they notified me of this. Unfortunately, due to me being a stubborn and immature guy back then, I decided to stay as I also held a B-2 visa, thinking that I could have continued staying as a tourist instead. I called an immigration lawyer for consulting and basically told me that I'm not allowed to find any other work and just stay put or get married to a US citizen (which I had no plans of doing so). So for the 5 months I overstayed, I just stayed at my (former) coworkers shared house and help with housework in exchange for helping them pay the rent and utilities as my name was under them (Again, I should have just switched the name to one of my coworkers instead). I only realized on the flight back to Hong Kong that I can only hold one status even if I had two visas, but I wasn't thinking of returning back anytime soon.

Fast forward to 2021, my brother is going to New York for university and I was planning on going with him just to see the campus for myself, while also visiting New York as a leisure vacation. I'm worried because even though my travel history showed that my I-94 had D/S, it might complicate things when applying for a new B-2 visa (I recently turned over my Philippine Passport in order to get a Hong Kong passport; effectively losing my previous B-2 visa, and becoming a permanent resident in Hong Kong). I really regret my decision to overstay and it's biting me in the ass which I really deserved, but I'm looking for any advice with regards to visa applications and once I arrive in the US. I have zero intentions of overstaying and I'm currently creating a thorough itinerary for my future stay, if ever I go through with it.

I appreciate any advice/help from you guys!!

submitted by /u/AdmiralLemonTea
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