Sex [or the lack thereof] and the City*

November

I was single, depressed, and ready to go hedonistically ballistic. Four years of monogamistic trial and error had come crashing to an end, and I wanted wild parties, loose babes, and intoxicated copulation. Unfortunately, the Playboy Mansion doesn't sell day passes, so I'd require an alternative locale. Immediately ruling out Seattle—I defy you to find a swim-up bar in this dreary town—I booked a week at the Hedonism II resort in Jamaica (see "It ain't no Temptation Island," below).

Though all in all the experience was a letdown, I did enjoy several weeks of Jamaican fun, sun, and spliff-enhanced fornication. But nothing lasts forever—without a trust fund.

December

I returned to Seattle wanting something less expensive, more consistent, and even (gasp) meaningful. My goal: to find a real date by Valentine's Day. Seven weeks, three days, and 18 hours to score a suitable engagement.

The objective was not to secure just any V-Day rendezvous whatsoever. Anyone can scrounge up a gal pal, companion, or sleazy bat to hang out with for an evening. (If you ask out every single person you meet for weeks, eventually you'll wind up with SOMEONE who'll agree to a free meal plus flowers.) But sitting with average Anne at a mediocre fixed-priced meal among red roses, helium balloons, and chocolate cherubs while gazing at dozens of lovely couples truly in love sounded worse than being alone.

No, at the ancient age of 36, I wanted something more.

Dates 1-7: SpeedDating

My first attempt at finding Mrs. Valentine came at a Jewish singles event known as SpeedDating. Participants meet seven dates, switching partners every 7 minutes at the sound of a bell—not exactly traditional matchmaking but not chopped liver either. At the end, each candidate fills in a "yes" or "no" card for every "date," indicating whether they'd like to see the person again. If a match is made, male mensches are provided with princesses' phone numbers (to be put on SpeedDial) and expected to call within four or five days.

Except for one woman who seemed to be on a time delay, the evening was actually enjoyable (even Attila the Hun would probably be good company for seven minutes). In the end, I had three names on my dance card, two of which "matched" (apparently kindergarten teachers are too good for unemployed, pot-smoking, kid-phobic playwrights). I followed up with Laura, a pretty, lithe brunette with a button nose(job) and peppy personality from San Fran. We laughed a bit on the phone, making small talk and not mentioning how many other matches we'd scored in the SpeedEvent—no one wants to look like too much of a polygamist on the first date.

We met at Serafina, a dark, romantic bistro and the location of dozens of my previous first dates. I'm comfortable there, the staff knows me, and if the dalliance works out, and my wife/mate/lover ever asks, "Honey, do you remember where we first met?" I'll be able to respond instantly that the fabulous encounter took place at Serafina, of course.

Meeting at 7pm, the idea was to have a quick cocktail and canap鬠and, on the advice of my sister, be out in 90 minutes tops—regardless of how well it was going.

Things did not go according to plan. Laura, who had not eaten lunch, downed a martini and was loopy within minutes. Slow service and fast metabolism meant the calamari would not be sufficient, and before I knew what hit me, dinner was on its way. Talk, talk, talk: College life, special moments, favorite books, and employment histories soared from our mouths till our throats were raw. We'd gone from 7 minutes to two HOURS and 7 minutes, too far of a stretch, leaving us both exhausted with little left to say, hoping we could get the barkeep's attention and blow this Popsicle stand before having to yawn in each other's faces and sending things into true Humiliationville. The last 20 minutes consisted of smiling weakly and staring at empty water glasses. Bottom line: Listen to your siblings.

Class Reunion

I decided to go deep in the well and fish out old yearbooks, foraging for past prom dates now divorced, out of rehab, or back in town after many moons away. As luck would have it, an old flame had just moved back from Philadelphia to take an Internet job (bad idea) after leaving her fianc頡t the altar (good idea). I'd last seen her four years prior during her engagement. In town for a mutual friend's wedding, we'd groveled in her rent-a-car like teens at a drive-in. Over the years, we'd dated sporadically, freaked out, and gone our separate ways.

Two dates into our latest bout, we were again groveling in cars, carpets, and carports. Our childhood crush was apparently alive and well 25 years later. Things looked good, if nothing else, to have a frequent sex buddy. I'd always been under the impression Alex had several relationships going at once and liked her more because of it. But before we could get into the details of a newer, more mature relationship, Alex headed to Hawaii for a week, and I was free to roam until her return.