Hedging my bets by dating a Libertarian hedge-fund manager

Broken at Love Contributor
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Last summer I dated a Libertarian, and I credit Serena Williams and Obama’s health-care plan with our break-up.

I’d met “Jim” on an online dating site. He was a 40-year-old hedge-fund manager, never married, and not bad looking. I brought my “A” game to our first date, wearing my go-to Match.com-meeting uniform (sleeveless black top, skirt, heels) and trotting out some of my best comedic material. It turns out I needn’t have bothered with anything more clever than knock-knock jokes; though he was kind, bright and perfectly pleasant, he wasn’t particularly interesting, and not at all funny.

But like a good dating soldier, I continued to bring the self-deprecating shtick, pulling (more than) my weight in the conversation, and Jim was apparently entertained by the banter. At one point he said to me, robotically, without even a hint of a smile, “You have a great sense of humor, Broken at Love girl.” There’s nothing like learning someone finds you funny by having him say as much in a complete monotone. He could have just, you know, laughed or something.

As we sipped our Shiraz, I didn’t particularly feel any sparks, but I wasn’t repelled. (I know, I know — “I wasn’t repelled” isn’t exactly the sweetest thing anyone’s ever said about a potential paramour.) So when he asked me for another date, I told myself, “Hey, this guy is harmless, and he thinks you’re amusing, and doesn’t seem fazed by the fact that the humidity has wreaked havoc with your hair.” Plus, he had offered to take me to a restaurant where they served the best lobster salad in the city. Never able to resist shellfish, mayonnaise, or any combination thereof, I agreed to see him for date No. 2.

The next day, armed with Jim’s full name and business card, I set about doing my due diligence: a comprehensive cyberstalk. What I discovered was more alarming than if he’d had a secret family or an active YouPorn account: It turns out Jim had made a sizable contribution to Ron Paul’s 2008 presidential campaign. Hmmm.

We hadn’t discussed politics on our first date, but I recalled that in his online dating profile, Jim had eschewed any of the options on the “very liberal” to “very conservative” spectrum and had instead chosen “some other viewpoint” to describe his political persuasion. (“Libertarian” is not one of the choices in the drop-down menu, nor is “sympathetic to Unabomber,” “Nostalgic for Reagan,” “Guilty Ivy Leaguer” or, the Liz Lemon special, “I try to do whatever Oprah tells me to do.”)

Concerned, I IMed a guy friend immediately with the news that my date was apparently an a-Paul-ogist. “But maybe he’s good in the sack,” my buddy offered helpfully. “How good could he be?” I wrote back, miserable. “He’s a Libertarian. I’d have to do all the work.”

Despite the revelation, I decided to move forward with the man my friends had dubbed Lobster Salad (a nickname my therapist, in a slightly disconcerting turn, also started using). My political views have always been liberal, but as a single New Yorker in her mid-30s, I wasn’t about to let a little thing like the rejection of government or any other authoritarian power keep me from meeting the potential father of my children. (See “Desperate, Getting.”)

On our next date, over the as-yummy-as-advertised lobster salad, Lobster Salad confirmed that he was indeed a Libertarian. But despite our vastly different political views, and despite the fact that the online advice column I’d found when I googled “dating a Libertarian” advised anyone in my situation to “run for the hills,” I decided to keep seeing Lobster Salad. I rationalized that his were not blind beliefs, but ones arrived at through extensive critical thought (or at least the consumption of a couple of Ayn Rand books).

Plus, Lobster Salad came from a working-class family from Queens, New York, and had worked to pay his own way through college — a “self-made asshole,” in other words. Somehow, this background made his political views more palatable to me. If he had been born into a life of privilege, I probably would have been less tolerant of his Libertarianism. But his backstory made him a sympathetic character. And I wasn’t getting any younger.

The relationship progressed. What I felt, I realize now, was not true affection for the Lobster Salad Libertarian so much as relief that I had found, after a significant dry spell, a boyfriend. I didn’t especially enjoy his company, but I was sure enjoying the visits to the summer house in the country and the dinners at expensive restaurants. I was so determined to plot an exit strategy from dreaded spinsterhood that I managed to ignore a fact that the friends who met him realized immediately: Personality-wise, the guy was a dud.

There were outward indications that even I could not ignore. For one, this was a wealthy, eligible, straight man who was actively looking to get married and have kids. The fact that, at 40, he had yet to be snatched up by any of New York’s desperate denizens did not bode well. It occurred to me that his blandness could be to blame. The guy had less charisma than the houseplant currently sitting on my windowsill, and it died several months ago.

Then there was The Curious Gifting Incident. One day on the phone, Lobster Salad let slip that he would have a present for me at our next date, but he refused to indulge me in my guessing game. Left alone with my imagination, I wondered if he’d gotten me flowers or chocolates, or if he was perhaps preparing a decadent dessert for the lady chocophile in his life. Then I got carried away: Was it theater tickets? A diamond tennis bracelet, perhaps? (He was a hedge-fund manager, after all.)

When the night of the date finally arrived, Lobster Salad ceremoniously presented me with … fruit-flavored gum. Apparently he had noticed my affinity for orange Trident, and decided, on a “romantic whim,” to pick me up a brand-new pack. Be still my beating heart.

Another ominous sign: our divergent ideas about vacations. When we started talking about planning a long-weekend getaway, I suggested the Caribbean, conjuring white sandy beaches, margaritas by the pool and decadent afternoon naps. He countered with Vermont. That could be romantic, too, I thought. We could take hikes, admire the foliage, and then snuggle up in front of a cozy fire, sipping apple cider.

Nope, that’s not what Lobster Salad had in mind. Instead, he wanted to find a place where he could learn telemetry — the art, he instructed me, sternly, of getting hawks and other birds of prey to land on one’s arm. Not surprisingly, the concept did not thrill me. Though I’ve been having steamy vacation fantasies since adolescence, none of the variations involves talon-on-skin contact.

We never made it to our fall getaway. The beginning of the end came when Edward Kennedy died. I’m a Massachusetts native who considered Kennedy a hero —a beloved figure who, despite the fact that he came from a background of supreme privilege, made advancing the rights of the have-nots his life’s work. I was glued to the coverage of Senator Kennedy’s funeral, which I found simultaneously wrenching and inspiring. Lobster Salad, perhaps predictably, told me he “hates the Kennedys” and brought up Chappaquiddick, asking me how I could mourn a murderer.

A week and a half after the funeral, President Obama made his health-care address to Congress. Moved by the speech, I foolishly abandoned my “agree to disagree” policy with the Libertarian and e-mailed him the portions of the transcript which I found most compelling. Didn’t he agree, I asked, that it was unconscionable, in a nation as wealthy as the United States, that so many citizens couldn’t afford access to health care? Big mistake.

In the icy e-mail exchange that ensued, Lobster Salad argued that a lot of people are “uninsured by choice — it just makes sense to them” or are too irresponsible or dumb to fill out the paperwork required to get coverage. He also, in referencing the dangers of demagoguery, compared Obama to Hitler.

I was tempted to break up with Lobster Salad on the spot, but a wise and reasonable friend intervened, suggesting that I wait until after the tennis tournament I was covering, when I would be calmer and less sleep-deprived, instead of making a rash decision that I might come to regret. With boyfriends at a premium in this city, a disagreement over health insurance premiums isn’t enough of a reason to toss one aside. The husband of another friend forbade me to ever break up with Lobster Salad, given that he was a hedge-fund manager with more money than the God he worshiped (in contradiction to his Libertarianism). “If you don’t want to date him, I will,” joked my friend’s husband.

Three days later, the final straw came in the imposing form of Serena Williams. I was at the U.S. Open covering the women’s semifinals on September 12, the night that Serena went ballistic on the court, unleashing a profane verbal tirade and, with menacing posture, threatening to shove a tennis ball down a lineswoman’s throat. It was a shocking scene unlike any other I’d witnessed in more than a decade of covering sports. I went back to Lobster Salad’s apartment after filing my story and breathlessly described what had transpired. He was sleepy and unimpressed by my account; purportedly a tennis fan, he said he had been unable to find the match on television earlier that night, and had gone to bed.

The next morning, we were awoken by the telephone. Lobster Salad’s mother was calling to discuss the Serena tirade, which 12 hours after the fact had become a national news story. I listened in disbelief as LS, using precisely the same words I’d used the night before, described the scene as if he’d been courtside. I’m not sure what bothered me the most — the fact that he didn’t tell his mother that I had been at the match; his shameless appropriation of my words as his own; or the fact that he was pontificating, with a tone of absolute authority, about an event in which he’d shown no interest the night before.

When he got off the phone, I asked him why he hadn’t mentioned me to his mother. Did she even know I existed? “She knows about you,” he told me, but I wasn’t convinced. And when I tried to engage him in a conversation about the women’s final, which I was looking forward to covering that night, he showed little interest in my assignment. Instead, he told me that he’d devised a new laundry-sorting system that had him “really excited.” He had abruptly shifted the conversation away from tennis whites and onto his own whites. I was done.

Two days later, Lobster Salad took the lead in our break-up conversation. He wanted to date someone “with an eye towards marriage,” he said over the phone, and I wasn’t someone he could see himself ending up with. My reaction should have been “ouch,” but instead I felt intense relief. I told him we weren’t a good long-term match because we didn’t have much in common.

“I don’t think that’s true,” he countered in his unintentionally deadpan tone. “We have a lot in common. You have a great sense of humor, and I like to laugh at all your jokes. And I have a great sense of humor, too.” I was silent for a few moments, appreciating the irony of a robot congratulating himself on his sense of humor. Then I burst out laughing. It was the first tears-free break-up of my life.

It’s too trite and Doogie Howser-esque of me to try to elucidate a lesson learned from each of my disastrous dating episodes. Most of the catastrophic chapters in the serial tragicomedy known as my love life have been painful, but not particularly instructive. I did learn something from dating Lobster Salad, though, and it’s not that people with sharply contradictory political views can’t live happily ever after. (If both partners are respectful of each other’s beliefs, why shouldn’t we all have a shot at what Mary Matalin and James Carville have?) Instead, I learned that it’s better to be alone than to force oneself to “make it work,” Tim Gunn-style, after you’ve realized you find someone’s company stultifying.

I’m glad I gave Lobster Salad a chance; I wouldn’t want to reject a potentially suitable partner after one date and then always wonder if I’d missed out on a perfectly nice guy. But I should never have hung in there as long as I did. I shouldn’t have wasted his time when he could have been meeting a laundry-loving lady who adores him. I wish I hadn’t been so slow to choose my own company over male company.

So new plan: Going forward, given the choice between a lifetime of singledom and a lifetime of tedium and telemetry, I won’t hesitate so much to choose singledom. Even if I have to buy my own lobster salad.