Sen. Rand Paul’s recent insistence that gay marriage “offends myself and a lot of people” serves as yet another reminder of the daunting challenge he will face on his way to 1600 Pennsylvania Ave.

Let’s examine the entangling alliances he must forge. All eyes are on Iowa, where around 57 percent of caucus-goers are self-described born-again or evangelical Christians. And guess what? “The base of the GOP is still overwhelmingly pro-marriage,” explains Steve Deace, a prominent Iowa Christian conservative radio host.

Ron Paul fell short of winning the state in 2012 with 21 percent of the vote, and it’s worth noting the last two winners were Mike Huckabee and Rick Santorum, respectively. Paul’s caucus calculus seems simple: Hold his dad’s vote—and add some additional Evangelical votes.

The problem lies with the more socially liberal libertarians and millennials that Paul hopes to court nationally. Keeping these disparate groups happy is sort of like trying to put a Rubik’s Cube together. In wooing one bloc, Paul risks alienating another.

His positions aren’t as inconsistent as they might appear. Unlike many libertarians, Paul has always been a fiscal and a social conservative. He differentiates himself from current GOP orthodoxy by stressing issues like ending military adventurism and domestic spying. But even here, Paul is finding it hard to keep everyone happy (see, for example, his joining with 46 other Republican hawks in signing an open letter to the “leaders of the Islamic Republic of Iran”—a move some libertarians are questioning).

The more Paul is forced to speak out on positions, the more opportunities he has to turn off supporters. For example, David Boaz, executive vice president of the Cato Institute, and author of The Libertarian Mind, likes Paul’s view of marriage as a contract, but suspects Paul’s newfound rhetoric about gay marriage comes with a cost.

“Unfortunately,” Boaz said, “it’s tone-deaf language that cuts against his goal of improving the image of the Republican Party with people who don’t trust Republicans.”

“I have no doubt that the senator is being honest when he says finds gay marriage ‘personally offensive,’” said Nick Gillespie, editor in chief of the libertarian Reason.com, in an email. “[T]he important thing is that Rand Paul is not letting his personal beliefs dictate national policy,” he said, pointing to examples where Paul has said government shouldn’t be involved in marriage.

“Many libertarians, especially from the Ron Paul wing, give him a pass on this because he did say essentially that marriage should be a private contract,” Boaz said. “Younger libertarians in particular,” he continued, “roll their eyes and declare ‘Well, he’s a conservative, what do you expect?’”

The conclusion seems to be that Ron Paul fans will stick with Rand no matter what, and although he may face stiff competition from the likes of Ted Cruz, Mike Huckabee, Rick Santorum, and Ben Carson, the younger Paul might even be able to peel off some additional Christian conservative voters.

If he does that, he can win some GOP primaries. The problem, it seems, is with the always dubious notion that Paul could rebrand the Republican Party in the long run, making it more appealing to disaffected millennials and tech-savvy libertarian denizens of the Pacific Northwest. This was always the hopeful promise of a Paul candidacy—the trade-off Republicans might accept in return for backing Paul.

But when push comes to shove, it’s hard to imagine too many mind-numbed whippersnappers flocking to a candidate who says the kind of things Rand Paul will have to say to win in Iowa. Paul would have to be willing to lose the primaries in order to win the general election. It was always a catch-22.