Phil Fragasso

Prologue - "When Jacob Met Nina"

 Every writer who’s ever confronted a blank sheet of paper, or the pulsing impatience of a digital cursor, dreams of discovering the literary Holy Grail. Capote found it in a blood-drenched home in a remote corner of western Kansas. Salinger found it in the voice of a disaffected teenager tottering on the edge of sanity. And Steinbeck, the show-off that he was, found it in pretty much every subject and character he chose to write about.

After twelve years of writing obituary notices and a teen advice column for a suburban Boston bi-weekly and collecting a Sunday-newspaper’s worth of rejection slips for three great American novels, I too have experienced a literary epiphany. I’ve come face-to-face with my own Moby Dick, and my life will never be the same.

And what’s really interesting is that none of this would have occurred if I hadn’t made out with a nun.

Now, in the interests of full disclosure, she wasn’t actually a nun. She was more like a novitiate or a nun in training or, as I liked to tease, a “nit.” And, if you twisted my arm so tight that my sphincter muscles felt loose in comparison, I’d admit that we did a lot more than make out. And if I were not the gentleman that my dear Nana Lillie taught me to be, I might even allude to the fact that it was right up there on my all-time top-five pieces of ass. But I’m jumping ahead or, perhaps, too far back.

The important thing is that I once boinked a nit and the great spirit in the sky felt obliged to smile down on me.


The irony is that I owe it all to a severe case of the hots for my sister-in-law, Tess. I was twenty when Tess married my brother, Mark. They’d met in college and married a year after graduation. Mark was an over-achieving simpleton with a goofball toothy smile and sports-imbued DNA that coaxed teachers and professors into granting him the benefit of doubt and awarding him extra credit just for showing up. Mark was able to turn a B-minus grade point average and a middling career as a Division 3 first baseman into a high-paying schmoozing sales job with a second-tier pharmaceutical company. He’s now an even more highly paid regional sales manager for a first-tier pharma company; and if I sound bitter and resentful and astounded at his success, it’s because I am. So enough about Mark. It’s Tess I really want to talk about.

In truth, I’ve always had a thing for my sister-in-law, even when she first started dating Mark and I was just a teenager trying desperately not to stare at her hips, thighs, breasts, and unmistakably heart-shaped butt. I realized from the very first moment I laid eyes on her that her legs were far too long, tanned, and toned to be touched by the stubby, paste-colored fingers of my brother. Her lips and tongue were too soft, plump and pink to be wasted on Mark’s slit of a pie hole, let alone the nether parts of his anatomy. When they were planning their wedding, I suggested that Joe Jackson’s “Is She Really Going Out With Him” would be an appropriate song for their first dance. Tess smiled and, at that precise moment, I believe she came to the realization that it would never work out for them but that the process was too far along to be stopped. So, less than three years later, I was neither surprised nor unhappy when Tess walked out on him.

“What took you so damn long?” was my telephone greeting when I called Tess to express my insincere sympathy about their separation.

I swear that I heard the beginning of a chuckle before Tess broke into a woeful sobbing.

“Tess, I’m sorry,” I stammered. “I was just trying to make a joke. Trying to lighten the moment.”

Her sobs were momentarily interrupted by a low-pitched grunt that I took as an acceptance of my apology.

“I mean I know this has to be very painful,” I said. “You guys seemed so happy together,” I lied.

“It’s been coming on for a long time,” said Tess as her sobbing turned into sniffling. “Then I found out the bastard had been cheating on me for over a year, so I told him to go fuck himself up the ass with a cactus and I left.”

I had always loved Tess’ colorful use of the English language. It was one of the many traits we shared and, hopefully, one of the factors that would draw us together for a lifetime of happiness and wildly imaginative, albeit steadfastly monogamous, sex.

Mark’s cheating, however, was a new wrinkle. I knew he was an asshole but cheating on Tess would place him alongside the likes of Tiger Woods and Jesse James as members of the Asshole Hall of Fame. Tess Botticelli, Elin Woods, and Sandra Bullock were women to be worshipped and adored. Screwing around on them was insanity incarnate. I knew Mark was stupid but I didn’t think he was mentally deranged.

“Holy shit,” I said. “I had no idea.”

“No one did,” said Tess. “He’s the all-American boy when there’s other people around, but he’s really a self-centered arrogant prick and I hope he rots in hell with his dick tied in a knot.”

I expressed my wholehearted agreement in at least a dozen ways and then asked if it would be okay if I stopped by some time.

“How about tonight?” said Tess. “I’m ready to move on with my life and it would be nice if you were part of that.”

“Perfect,” I said and then hung up before she had a chance to change her mind. She wanted me to be there when she moved on with her life. She wanted me to be part of it. Move over big brother, there’s a new Botticelli in town.

Of course, that’s not the way it turned out. What Tess meant was that she wanted pretty much everyone she’d ever known to join her in moving on. When I arrived at her house (and based on the divorce settlement, it was now one-hundred percent her house), the crowd was overflowing onto the front lawn, backyard and driveway. Music was blaring, everyone was drinking, and the sweet scent of weed wafted overhead. It took me a good fifteen minutes to track down Tess and, in return, I got a dry peck on the cheek and a “thanks for coming” as she drifted through the drunken throng (try saying that five times fast).

My dream of eternal bliss alongside Tess’ heaving breasts having been summarily shattered, I quickly assessed the situation. I was at a party with a two-to-one ratio of women to men, plenty of beer and wine, and nowhere else to go. I downed a Blue Moon white ale, grabbed another cold one, and began my search for either the perfect woman or any other woman who would have me.

I spotted her sitting alone on the edge of Tess’ pool, her legs flapping in the water and her shoulders swaying to the beat of some Madonna-wannabe, one-hit-wonder pop star. She was wearing a two-button white polo shirt and Nantucket red shorts. Her hair was shoulder length, brown with auburn highlights, and somewhere between frizzy and naturally wavy. Compared to the hard-partying hard bodies showing off their wares, she seemed quiet and plain. I figured she’d be easy to impress.

Novelist & nonfiction author