As Mitt Romney struggles to convince conservative Republicans that he is no "Massachusetts moderate," his opponents have had plenty to dredge up from the 1994 Senate campaign when he positioned himself to the left of liberal icon Edward Kennedy. No issue has proved thornier than gay rights.

Romney's evolution on the matter is well documented. When running for the Senate, he told the New England GLBT newspaper Bay Windows that he believed "the gay community needs more support from the Republican party and I would be a voice in the Republican party to foster anti-discrimination efforts." During a Pride weekend parade in 2002 when he was running for governor, his campaign famously distributed pink flyers saying "all citizens deserve equal rights, regardless of their sexual preference." And during his years in Massachusetts, whether addressing civil unions or gays in the military, Romney offered plenty of fodder for then-GOP presidential candidate John McCain's 2008 opposition research book.

But just how open was he at the time? Very open, according to interviews conducted with two former members of the Massachusetts chapter of the Log Cabin Republicans.

They told The Huffington Post about a previously unreported moment in which Romney revealed what they described as an unusually high degree of comfort with gays. The moment took place at the Claddagh restaurant in Boston's South End neighborhood on Sept. 7, 1994, as Romney sought the group's endorsement. About 80 prominent gay Republicans gathered to hear Romney discuss taxes, balanced budgets and other staple GOP talking points. The crowd peppered him with questions.

The men, who spoke on condition of anonymity because they are no longer involved with the group or politics, said Romney was asked what he would do if one of his five sons told him he was gay.

"Without missing a beat, he said, 'How do you know that hasn't happened?'" recalled a lawyer who said he was in the room. "He went on and made it clear it hadn't. But it was an interesting thing to say."

"It was not a 'stiff politician' reaction, not a stock response," the lawyer added. "To me, it demonstrated a sort of comfort level you don't see in a lot of politicians."

A second source, a businessman, confirmed the remark. He said there was "no hemming or hawing" by Romney. Instead, he said Romney gave an "un-candidate, unscripted" response that was unusual for most politicians who were asked similar questions by gay constituents.

"You get responses from people like ' uh, uh, uh.' Very uncomfortable," the businessman added. "There are people in life who you get the sense that they are uncomfortable when they know you're gay. He's not one of them. He's pragmatic.... He judges people by what they can do."

A request for comment to the Romney campaign was not returned.

Given how Romney's current campaign has been roiled by gaffes suggesting a certain tone deafness, the Claddagh event nearly two decades ago offers a different, less publicized, side of Romney.

"He did project a very high comfort level being around gay people, talking to them," said the lawyer, who said he met with Romney many times during his Senate and gubernatorial races. "There are others, including some who have been very supportive legislatively, who showed a visceral level of discomfort."

The Log Cabin chapter would later endorse Romney, although he ultimately failed to unseat Kennedy, who had strong backing from the wider, Democratic-leaning gay community.

Gay Republicans stood by Romney during his run for governor in 2002, but soured on him two years later when Massachusetts' highest court became the first in the nation to sanction gay marriage. The candidate who once wrote in a 1994 letter to Log Cabin Republicans that "we must make equality for gays and lesbians a mainstream concern" announced that as governor he would support a constitutional ban on same-sex marriage.

Log Cabin Republicans who had enthusiastically endorsed Romney were devastated, as were many other members of the gay community. Many chalked it up to national ambitions far from the blue precincts of Massachusetts and, as Romney's more recent statements have shown, he seems to have had no problem moving right to appeal to more conservative voters.

For the two gay Republicans who were once so enamored of Romney, the 2012 election finds them looking elsewhere. Both supported former Utah Gov. Jon Huntsman -- until he dropped out and endorsed Mitt Romney this week.