A Kosher Dating Odyssey: One Former Texas Baptist's Quest for a Naughty & Nice Jewish Girl (13 page)

Through it all, I can vouch for the song saying that, “romance without finance” won’t work out. For the first two-plus years of my single life, I struggled with post-divorce credit card debt into the five figures. I chipped away at the total (tracking the agonizingly slow progress on Quicken, of course), but I still didn’t have the cash for a swinging social life. All it took was one big repair on my creaky, clanky 1986 Saab sedan to throw my financial progress into reverse. I found the resources to fly down to Brazil, but otherwise I felt constrained.

My financial profile changed dramatically when I paid off the credit cards. I could finally take a deep breath, crank up my 401(k) contributions and think about how I could manage a real pursuit opportunity. The records show a sharp increase in spending as I often followed one date with another a day or two later. On one February 1, I ate at McArthur’s American Grill with Joan. On Feb. 6 I ate at the Evergreen Shanghai Restaurant in New York with one woman; the next day I ate at the same place with a Princeton friend I’d pined for two decades earlier (until we got together for Chinese food in Greenwich Village and she started chatting about her boyfriend).

I bought the mighty Weil for $39.02 (I saved the receipt), using a corporate gift card. My doleful prediction came true; I never gave it to Mala, and the longer it sat in my closet, the less inclined I was to present it to anybody. It just didn’t seem right. So it just stays on the shelf next to the floss and light bulbs. If anybody wants a pristine, unopened (really!) vibrator, gently wrapped in unrequited dreams, just let me know and we’ll arrange a handoff.

How do I define ROEI, return on emotional investment? The crudest, most obvious measurement would be cost per sexual encounter. However, that doesn’t capture the range of value a relationship can deliver. I like to think a relationship, even if it stays at the level of friendship, provides something worthwhile. If sex is the only payoff, then that’s a recipe for a wretched ROEI. So we could start with a denominator being the total dollar amount spent. The nominator would combine the positive and negative aspects of the relationship. That would be the cube of the number of Passover seders, Fourth of July BBQs, Thanksgivings and birthdays observed together, plus (number of cuddly encounters times the value of pi) minus number of angry discussions of the status of the relationship times number of breakups.

Inasmuch as I flunked calculus at Princeton, I’m the wrong guy to devise a mathematically precise quantitative analysis for ROEI. The concept works best as a descriptor of a relationship. In some I made a huge emotional investment and got almost nothing back; let’s call that my Madoff madness, throwing emotional capital into an opportunity long after I should have taken my losses and pulled the plug. Then others rewarded my good judgment and pay dividends regularly.

The intellectual delights of ROEI finally faded away. I just stopped caring—for the best reason. For the last four years I’ve been in a relationship that works well and I don’t even try to figure the ROEI. That’s one of the nicest parts of a stable relationship—the numbers stop mattering when the living works out.

In addition to ROEI, my years in the dating jungle led me to develop another useful framework. Somewhere in my ill-spent years as an economics major at Princeton, I learned the concept of investment diversification, or modern portfolio theory. That means, in essence, don’t put all your eggs into one basket. By spreading your investments among different options, you lower the relative volatility of your portfolio (the “beta”) and have a more stable rate of return. You can either aim to focus on maximizing return or minimizing risk. So go ahead and have a fling on a dot-com start-up or sub-prime mortgage fund, but don’t skimp on the index funds and Dow Jones industrials.

In my madder days of dating, I thought of my activities as an exercise in portfolio theory.

I’ll admit that the goal of a dating strategy runs exactly opposite of real portfolio theory. Dating strategy for most people aims to find the
beshert,
the one man or woman to whom you commit and cherish. Financial portfolio theory means you forsake the one for the many, holding and adjusting a basket of diversified investments that, so the theory goes, will not all go up and down at the same time. Some rise, some fall, but the result is you never get totally hosed. In real life, I do that with investments in stock and bond index funds.

In the online dating world, I didn’t know what would work. I didn’t want to remarry right away; it took years to even hold hands with a woman. While some people bring a laser-like focus to online dating—locals only, marriage-minded, must want children, can’t have young children, and must keep kosher are among the valid limitations—I didn’t set hard limits. I had a pretty clear idea of the kind of woman who appealed to me and I would look for them all over. No location was too far or too close. I was in touch with one woman who actually lived in my apartment building in Connecticut—we swapped emails and waved to each other in the basement laundry room but never mustered enough enthusiasm for even a cup of coffee. Yet, I flew 5,000 miles to Brazil to spend a week with a woman. In between these extremes, I had contacts with women all over the world—Israel, Canada, Latin America, California, Florida, Texas. So I diversified my dating portfolio to enhance returns rather than limit risks. I took some risks, and, looking back, heck, I should have taken a few more. If one prospect bitterly disappointed me, I had others in the pipeline. That might be a formula for emotional chaos, but diversification kept any one flame-out from leaving me feeling totally crushed (in theory, anyway).

I was so diverse I didn’t know if I was coming or going. Had I possessed unlimited funds and leisure, I could have devoted all my time to world dating travel, hitting synagogues globally in the process. Moldovans in Silicon Valley, Romanians in Texas, Texans in New York, New Yorkers in Israel, Israelis in Westchester County, Mexicans in Canada, and all the Girls from Ipanema—our circles intersected and sometimes we actually met. When not wracked with despair, I had fun.

Looking back, I made some good friends through the portfolio approach. Relationships developed, although many were hampered by distance.

And that gets to the crux, perhaps, of why I expended so much energy scouring the world. Distance—keep them at arm’s length, always have a reason for not meeting. While some couples make long-distance romance work, they ultimately need to close the distance for the relationship to thrive. Otherwise, a frustration factor kicks in. If children and custody schedules enter the mix of issues, the balancing act becomes even more difficult. My rule of thumb might be that two hours’ travel sets the outer limit for a workable relationship. Beyond that, the process gets far iffier.

When I finally found a relationship that became stable, close and enjoyable, the woman lived forty-five minutes away. She was born in the United States. English is her first language. We both graduated from Ivy League schools in the same year. After all my wanderings, I found success close to home, rather than close to the Equator. The beta in my dating portfolio vanished as an issue—now, if only my real-world 401(k) performed so well!

Online dating fit well with my personality. It meshed with my sharp sense of self-knowledge and self-promotion. I knew how to describe myself in terms that appealed to certain kinds of women. That’s what every guy hopes to do, but I knew how to hit the Jewish, Southern and literary angles that were catnip to certain women. That knack for sincere self-expression was the secret weapon that helped me at least get my foot in the dating door. Whether the door subsequently was slammed in my face is another issue.

Online dating also was a great fit with another quirky side of me: my relentless desire to document my life. This collecting and categorizing no doubt stemmed from a childhood desire to make sense of the world, to record my impressions and ease the growing isolation I felt growing up. I never knew my grandparents, for example, and I was determined to create my own history for later generations to read. From the age of twelve, I reported on my own life in a journal.

Besides the journal, I kept files of my literary works. In 1973 I started a literary folder called “Projects, et. al.” to hold poems I had written like “Junkie’s Lament,” “A Watergate Trilogy,” and “Faded Ponies on a Merry-Go-Round.” Short stories included “Our Trip to the Mortuary,” about an imagined grade-school field trip, and its delightful sequel, “Our Trip to Reynosa,” about a sleazy town on the south side of the Texas-Mexico border.

The folder held melancholy teenage poems like “Just Friends” and this note from November 1972. Probably stuck in my locker at Mission High School, it sounds remarkably like emails I would linger over thirty-five years later:

My life and interests evolved. After I left Texas for Princeton and then New York, I had regular (as in, required!) mail correspondence with my mother. I saved every letter she ever sent me, and made carbon copies of letters I wrote to her on IBM Selectric typewriters in the pre-desktop publishing era.

When I arrived in New York, I followed “Projects et al.” with a manila folder dubbed “The Love File”—a record of my search for romance. The idea struck me in June of 1980, during the weeks after I graduated from Princeton and moved to Brooklyn. I read an article in
New York
magazine, “A First Avenue Romance,” about the adventures of twenty-somethings Barry and Debbie in the New York singles scene. The article whispered about the potential of my new urban life after affection-deprived college years. I thought, “I’ve got to hang on to this for future reference.”

For eight years, the Love File swelled with articles, letters and pictures related to my quest for connection. Meandering through its pages, I feel like an emotional archeologist. Every scrap of material hints at my hopes and anxieties. The files include articles that rocked nervous singles of the mid-’80s, such as the notorious
Newsweek
“Marriage Crunch” cover article from June 1986 warning that college-educated women “still single at the age of thirty-five have only a five percent chance of ever getting married.”