CNN
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As the Supreme Court gathered for more than two hours on Monday to discuss whether a graphic designer can refuse to do business with same-sex couples, the justices somehow strayed into dueling hypotheticals concerning Black and White Santas and dating websites.

Hypotheticals are nothing new at the high court as the justices probe how cases before the court could impact different challenges down the road. But Monday’s hypothetical was unusually awkward, with a reference to children wearing a Ku Klux Klan outfit to visit Santa Claus.

It all began when Justice Ketanji Jackson expressed some alarm about the extent of arguments put forward by the graphic designer, Lorie Smith, who wants to expand her business to celebrate marriages, but does not want to work with same-sex couples out of religious objections to same-sex marriage.

“Can I ask you a hypothetical that just sort of helps me flesh” this out, Jackson asked a lawyer for the designer.

Jackson wanted to know about a photography business in a hypothetical shopping mall during the holiday season that offers a product called “Scenes with Santa.” She said the photographer wants to express his own view of nostalgia about Christmases past by reproducing 1940s and 1950s Santa scenes in sepia tone.

“Their policy is that only White children can be photographed with Santa,” Jackson said and noted that according to her hypothetical, the photographer is willing to refer families of color to the Santa at “the other end of the mall” who will take anybody, and they will photograph families of color.

Jackson asked Kristen Waggoner, Smith’s lawyer, “why isn’t your argument that they should be able to do that?”

Waggoner finally said that there are “difficult lines to draw” and said that the Santa hypothetical might be an “edge case.”

That drew incredulity on the part of liberal Justice Elena Kagan.

“It may be an ‘edge case’ meaning it could fall on either side, you’re not sure?” she asked.

Jackson returned to her query later and expanded it. She said her hypothetical photographer is doing something akin to the movie “It’s a Wonderful Life” and wants it to be “authentic” so that only White children could be customers.

Waggoner suggested that in the case at hand the “message wins,” but never really explained what she meant.

Artist explains why she thinks she shouldn’t have to work with same-sex couples

When a lawyer for Colorado stood up to defend the state’s anti-discrimination law, Justice Samuel Alito chimed in.

He wanted to know if a Black Santa at the other end of the mall doesn’t want to have his picture taken with a child who’s dressed up in a Ku Klux Klan outfit whether the Black Santa has to do it?

Colorado Solicitor General Eric Olson replied that there is no law that protects a right to wear a KKK outfit.

That spurred Kagan to jump in, noting that objection would be based on the outfit, not whether it was worn by a Black or a White child.

Alito then uttered an extremely awkward aside that could have been an attempted joke gone astray. “You do see a lot of Black children in Ku Klux Klan outfits, right? All the time.”

At another point in arguments Alito was posing a set of hypotheticals and again engaged Kagan – his seat mate – as he searched for how the case at hand could impact other cases.

He was referring to a “friend-of-the-court” brief filed by lawyer Josh Blackman on behalf of the Jewish Coalition for Religious Liberty in support of Smith. The aim of the brief is to discuss problematic situations for Jewish artisans who object to speaking out about certain topics. A series of hypotheticals was included to show instances in which a Jewish artist would be compelled to betray his conscience.

“An unmarried Jewish person asks a Jewish photographer to take a photograph for his JDate dating profile,” Alito began, referring to a hypothetical in the brief.

He paused. “It’s a dating service, I gather, for Jewish people,” Alito said.

Kagan, who is Jewish, chimed in to laughter, “It is.”

Alito decided to plow awkwardly forward with another hypothetical from Blackman’s brief .

“All right. Maybe Justice Kagan will also be familiar with the next website I’m going to mention,” he said. “A Jewish person asks a Jewish photographer to take a photograph for his Ashleymadison.com dating profile.”

The audience laughed as Ashleymadison.com appears to refer to an online dating service and social networking services marketed to people who are married or already in relationships.

It was another awkward moment with Alito adding: “I’m not suggesting that – she knows a lot of things. I’m not suggesting – okay … Does he have to do it?”