There is a reason mothers everywhere get apoplectic when their children stick their hands out the car window. Barack Obama, who is determined to “extend a hand” to nasty regimes snubbed by the previous administration, has already received two hard lessons in this maternal wisdom.

The first came in the form of a May 25 nuclear weapons test by North Korea which dashed any early hopes for a rational dialogue with the communist dictatorship in Pyongyang.

Now, less than a month later, an election in Iran has sown violence and chaos, with Mahmoud Ahmadinejad, the aggressive and anti-Semitic incumbent, claiming victory, while more moderate Iranians who yearn for better relations with the West and economic reforms at home have taken to the streets to protest what they view as a stolen election.

The dilemma this creates for the United States isn’t hard to see. Attempting to establish a conversation with Iran’s government is central to the so-called “smart power” strategy Obama’s foreign policy team has espoused. Yet the president’s confirmation that dialogue with Iran will remain a goal of his administration — regardless of which way a review of the vote count goes — has left America’s hand dangling before a regime that may have just stolen an election.

It may be that the world will never truly know the real outcome of the Iranian vote. Electoral legitimacy for Ahmadinejad may now be impossible even if the election is confirmed by the Guardian Council, a panel of senior mullahs who have been ordered by the country’s supreme religious leader, Ayatollah Ali Khamenei, to review the results. A decision is expected early next week, and opposition leaders already have said they suspect the review is just a delaying tactic designed to allow the backlash to abate.

But this only heightens the dilemma faced by Obama. Already, voices on the American right who resent the subtle pressure Washington has applied on Israel over its continued settlement construction in the West Bank are rounding on Obama over the Iranian vote: “Someday a future president may have to apologize to Iranians for Mr. Obama's nonfeasance,” Wall Street Journal op-ed columnist Brett Stevens wrote Tuesday.

Yet much of the Obama team’s thinking with regard to the wider problems of the Middle East — the “Greater Middle East,” if Afghanistan, Pakistan and Iran are included — depends on successfully convincing whichever leader assumes the helm in Tehran that going nuclear will destabilize the entire region and put Iran on a collision course with forces it cannot defeat.

Sanctions and international tisk-tisking, after all, have done little to deter Iran from its pursuit of nuclear weapons technology, Obama’s aides argue. And the fact that American troops virtually surround Iran (in Iraq and Afghanistan) has done little to temper Iran's behavior. If anything, it arguably gives Tehran even more incentive to pursue a nuclear shield.

So some kind of “grand bargain” must be attempted. Even if it is not likely to work, this line of thinking goes, attempting some kind of outreach is a prerequisite to either of the other two policy options: living with a nuclear Iran, or attempting to prevent a nuclear Iran by military force.

Obama’s senior Iran advisers — most notably Dennis Ross, who has just left a State Department post to spearhead Iran policy from within the White House — believes there are things Iran wants that could form the basis of such a bargain. These include international legitimacy, trade and investment with the West, a voice in the future of Afghanistan and Iraq, and a seat appropriate to its rising regional power at the world’s global forums.

That “bargain” was going to be hard to drive with the inflammatory Ahmadinejad even before last weekend’s election. Now, add a question mark about his election, and the betrayal moderate Iranians might feel if America continues to reach out to him, and the challenge becomes almost impossible.

Click here for an overview of GlobalPost's coverage of Iran's election.

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