In the fall of 2008 I had dinner with two Jewish friends for the last time. Already then we saw each other rarely, but they had done me the favor of traveling up to the far east of the Upper East Side to an Israeli place where I could eat kosher meat, at the time a fresh commitment.The conversation is hazy to me. It turned at some point to the impending election (one of the two was wearing the “Barack the Vote” T-shirt popular at the time) and Israel must have come up.What did I say? Something about Obama’s weak record? A mention of Rashid Khalidi or Jeremiah Wright? I’m sure I was too passionate, probably even pedantic.I learned later that I had exasperated them. About that I can’t complain: The person sitting at the table criticizing the Democratic candidate was the same one who earlier in the year had been walking around with an Obama-for-president sticker stuck to his T-shirt.It was bad enough for my two friends to be told over dinner that their concern for Israel should force them to reexamine their political commitments. Worse for it to come from a friend who had become unrecognizable from the leftist they once knew.For me, as for many of his early supporters, Obama’s appeal had been based on his depiction of himself as a politician who was above politics. But his response to the Wright controversy, and later, when he broke his promise and accepted public funds for his general election campaign, made it clear to me that the Democratic candidate had more powerful motivations than changing the way things work in Washington. Once I saw him as a politician like any other, I couldn’t justify throwing my support behind a candidate who had no significant record on foreign policy and Israel.They say you should never speak about politics or religion at a dinner party. Ditto for lecturing about those—or any other topics—to friends you’d like to keep. But unlike others, for whom politics had always animated their friendships, I was someone who made my close friends when politics was something I cared very little about. Perhaps that’s why losing them came as such a shock.***If there is a beginning to my political transformation, it started in the Ecuadorian rainforest, where I went to live for a couple of years as a Peace Corps volunteer after I graduated from college in 2000. When I wandered out of the remote town where I lived as one of a handful of non-Ecuadorians, the Westerners I spent my time with were other Peace Corps volunteers or Europeans, eager for a picture with the natives, beating around a corner of the Third World.I found myself often disagreeing with them: the Brit in a dark street in Baños, a small town in the mountains popular with tourists, who insulted George Bush when I asked him for a light and he heard my accent. The lone Dutch tourist who made it all the way to Puyo, the largest of the Ecuadorian rainforest’s small cities, and invited himself into a hostel room I was sharing with an American friend to lecture us on the impending world war driven by American thirst for oil. The embarrassed whispers among my Peace Corps friends when they saw fellow American tourists in Cuenca.The strongest disagreements, though, turned out to be over Israel. I had been sent to Hebrew school and a Jewish summer camp and performed the rudiments of a bar mitzvah ceremony when I was 13. I moved passively through these experiences, picking up little, and thus understanding little about the Jewish state.But there must have been some sort of latent emotional attachment, because it was with shame that I discovered I had nothing to say when I heard wild things said about Israel that I knew could not be true: a casual invocation over chess of Israeli “slaughter” of Palestinians, a justification on a walk to buy beer of suicide terror as the desperate act of a people with no other choice, a dismissal of Zionist claims by noting (falsely, I regret to add) that there are more Jews in New York than in Israel. Everywhere I found an unthinking identification with the Palestinians and condemnation of the very idea of a Jewish state as chauvinistic, oppressive, and anachronistic.These accusations stayed with me when I made my first trip to Israel in 2003, the year after my departure from Ecuador. They gradually become elements of an ongoing argument I had in my head with interlocutors without names. They said, “Jews need to just stop moving there because it’s pissing people off,” and I explained in response the necessary and just relationship of a nation-state to its diaspora.New York, I also learned, could be similar in its condemnations and negative impressions of Israel. A colleague at a public school where I was teaching told me that the small northern Israeli city of Sfat was a “sad” place to visit. Another teacher made plans to bring an International Solidarity Movement representative to speak to the tenth grade. Meantime, I was getting addicted to Israeli news websites, struggling through Josephus, and leaving copies of Alan Dershowitz’s The Case for Israel in my colleagues’ mailboxes.Among friends, the conversation was less aggressive than it had been in Ecuador, but it was similarly troubling. New York, these friends maintained, might not have more Jews than all of Israel, but it did have more than Tel Aviv, which they somehow thought was a point of substance against Israel’s legitimacy. More often, Israel was a topic of boredom and, for some of my Jewish friends, embarrassment. This wasn’t because they knew much about it, but because they knew it as a place that didn’t receive gentle coverage in their favorite publications.To all this I spoke up, never imagining it would raise any questions of loyalty among my friends. For those whom I discovered were my true friends it didn’t, even if we often disagreed. Those whose friendship turned out to never have been as strong as I imagined began trading around stories of my “Zionist freakouts” and made plain, in one way or another, that my company was something they could live without.Lost friends are the common experience of all adults. But I suspect that the ones you lose in your twenties must hurt the most; they are the friends you made as a teenager, telling yourself that you’d be friends forever.I have no survey to prove this, but I suspect that much of what is thought of as young American Jewry’s distancing from Israel must be more about avoiding hard conversations with close friends than anything else. Israel’s cause has probably never been less popular than it is today in the cities where most young Jews live. Saying something kind about it carries with it a potential social cost most young adults would simply prefer not to risk—despite their personal feelings. Silence, and waiting for a more amenable topic, is an easier option.If given another chance, I would handle that night in the fall of 2008 differently. I wouldn’t stay silent, but I would have changed my tone. Stubbornly voicing my opinion guaranteed that my views would fall on deaf ears. If I had had a real conversation with my two friends, who knows, perhaps they would have changed their minds. That’s what I’ll be thinking about—and I hope doing differently—this election season.***Like this article? Sign up for our Daily Digest to get Tablet Magazine’s new content in your inbox each morning.Matthew Ackerman is the media relations manager for The David Project, a nonprofit that positively shapes campus opinion on Israel. Follow him on Twitter @MatthewAckerman.