To a large degree, the couple is stuck. While the American information technology consultant and Venezuelan pet groomer wed at a romantic Connecticut ceremony last year, the federal government won't recognize the marriage between the two men -- and as a result, won't approve their application for a green card.
But the couple, and others facing a similar predicament, are still trying. The men don't expect to actually obtain a green card any time soon and have already been shot down once but hope filing an application might convince an immigration judge to at least refrain from deporting Benshimol while the fiery legal debate over the country's same-sex marriage laws simmers.
"There have been so many ups and downs on this roller coaster. I really don't know what to expect," said Gentry, 53. "It can't hurt (to refile). All they can do is deny it again."
For years, immigration attorneys warned gay couples not to bother seeking a green card for their foreign spouses since there was no chance they'd get one. Now, in select cases, they're starting to rethink that advice.
In the wake of the federal government's announcement that it will no longer defend a law that defines marriage as between a man and a woman and a court ruling raising questions about the law, some immigrant advocates have suggested that gay couples fighting deportation apply for a green card in a final effort to stay in the country.
Most couples, advocates say, should refrain from doing so to avoid drawing attention to their predicament if the foreign spouse is here illegally, and to avoid forking over cash for a benefit they won't get anytime soon if here on a legal visa.
But the small group of couples already facing deportation has little to lose by applying, and might see some gain.
In March, an immigration judge in New York halted deportation proceedings involving a lesbian couple until December. Last month, an immigration judge in New Jersey did the same for a Venezuelan salsa dancer married to an American graduate student after Attorney General Eric Holder asked an immigration appeals court to review another case involving a same-sex couple.
In a memo posted to its web site in March, the American Immigration Lawyers Association suggested that couples facing deportation consider filing for a green card in the hopes that it might win sympathy from an immigration judge willing to put the case on hold or bolster the immigrant spouse's case for an asylum petition.
"We are advising more people to do it -- at least in the context of if the foreign partner, the foreign spouse is in deportation proceedings," said Victoria Neilson, legal director of Immigration Equality, an immigrant rights group focused on the gay and lesbian community. "At this point there is more of a feeling that the tide is turning on marriage in this country and it could be something that could be helpful."
U.S. immigration authorities are denying green cards for same-sex couples because the 1996 Defense of Marriage Act specifies that marriage is between a man and a woman, said Chris Bentley, spokesman for Citizenship and Immigration Services. As of March, the agency had 10 or 20 such petitions pending, he said.
There are roughly 26,000 bi-national same-sex couples in the United States where one partner is a U.S. citizen. There's no estimate on how many have legally married, said Gary Gates, a UCLA professor and co-author of the Gay and Lesbian Atlas.
It's impossible to know how many couples filed green card petitions before last year, immigration authorities said.
Lavi Soloway, an immigration attorney in Los Angeles, said he started encouraging some clients to apply last year after a federal judge in Massachusetts ruled the 1996 Act is unconstitutional because it interferes with a state's right to define marriage.
Soloway saw further encouragement this year when Holder said the executive branch would no longer defend the Act as constitutional and the immigration agency temporarily held off making a decision on same sex couples' cases.
"The forum in which we're testing the issue is immigration court," said Soloway, who represents a dozen couples including Gentry and Benshimol. "It is the best possible place for this discussion to be taking place because it involves parties that have broad discretion to address just the kinds of concerns we're talking about."
Immigration and Customs Enforcement -- which is responsible for carrying out deportations -- said the agency will continue to enforce the law unless it is repealed by Congress or shot down by the courts.
The issue has enflamed passions on both sides of the debate over gay marriage.
It has also raised questions for those seeking stricter limits on immigration. Mark Krikorian, executive director of the Center for Immigration Studies, said judges can exercise discretion on individual cases but shouldn't use that power to enact sweeping policy changes.
"They are in effect legislating and it's not their job. It's Congress' job," Krikorian said.
Benshimol came to the country 12 years ago and overstayed his tourist visa --an immigration violation that straight couples can remedy once married. Now, he says he can't safely return to Venezuela as an openly gay man and also can't stand the thought of being separated from his husband, or of forcing Gentry to leave behind his adult son and daughter who live in California.
Even so, Gentry and Benshimol say they are hopeful, simply because they have no other choice.
"You just never know. The analytical side of my head says, you know, DOMA exists and it's the law and they're going to deny it," Gentry said. "But then the hopeful side of your brain says, you know, there's a chance."