Two entries on an ESTA in the same year?

My boyfriend and I have been together for just over two years. He’s Chilean and we met during his first time in the USA in July 2019. He departed at the end of July 2019.

I went to Chile in January of 2020 and returned to the USA at the end of the month. I went back to Chile in December of 2020.

When I left Chile at the beginning of February 2021, I brought my boyfriend with me and he stayed through the end of March 2021.

All of his time spent in the USA (July 2019 and February-March 2021) was on an ESTA.

I had planned to return to Chile in August, but their borders aren’t open to non-resident foreigners and I can’t acquire salvoconducto at the embassy since it isn’t an urgent need/emergency. Since I spent the holidays with his family last year, he wants to spend the holidays with my family this year…but he’s worried that he’ll be denied entry (most likely in Texas) since he was already here in 2021.

He’s a full time student with plenty of documentation indicating that he plans to return to Chile, but since we want to apply for the K1 eventually we don’t want to risk him being denied entry.

Do you think there is anything to worry about? His entry would be about 9 months after he last left the USA. He last stayed for about 6 weeks.

submitted by /u/coqowl
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