Back in the Game

The last time I was single, the Yankees were on top of baseball and on their way to their fourth World Series win in five years. Bush needed Florida’s recount to win his first term, Angelina Jolie won a Best Supporting Actress Oscar and researchers completed mapping the human genome. The millennium was still brand, spanking new, as was my relationship with a fantastic woman.

Five-plus years later, the Evil Empire from the Bronx has yet to win another World Series. I’m not completely consoled because my Atlanta Braves haven’t won one, either, but sports disappointment is nothing. That fantastic woman and I have split up. After nine months on my own, I figured I was as ready as I could be and needed to move on. Thing is, I left dating at 26; I’m now 32. Grumpy, old man? Hardly. But I’m not clubbing with my wingman Jack Daniels till dawn on a Tuesday, either. I thought I’d ease myself into the dating world by exploring options not as available or attractive my last time ’round.

"At the same time, less than 48 hours after joining, a supposed woman from Alabama asked me for $750 and wanted to stay at my place, claiming love at first sight. It was scary, not flattering."

I’d always heard it gets harder to meet people as you get older. Online dating seemed to offer a solution to that problem, so I signed up for, one of the largest Web-based dating services available. For 30 bucks a month I was able to post my own profile and view those of about 500 women who fit my search criteria, which, save for a few things, were pretty open: i.e., ages 24 to 40; any ethnicity; within the state of Hawai’i; height from four-foot-10 to five-foot-10; with or without children. While researching other Web options (see, I also learned of more group-specific services, and I joined one of these,, at just under $19 monthly.

Things didn’t go so well at first. I naively assumed that these women would already know I was a good guy, and boldly e-mailed more than a few, asking them if they’d like to go out, and & got silence in return. It was frustrating to learn Web protocol often involves long periods of e-mail and phone conversations before a face-to-face ever happens. At the same time, less than 48 hours after joining, a supposed woman from Alabama asked me for $750 and wanted to stay at my place, claiming love at first sight. It was scary, not flattering. (I responded with condolences, but used the tool to bar her from further contacting me). The Web thing really wasn’t for me; I met a handful of pen pals, but did not go on a date.

Exhausted and without real prospects in the World Wide scene, I tried one of the local alternatives, Party of Six. A singles organization downtown owned by Dee Dee DeSoto, professional matchmaker, Party of Six sets members up in six-person group dates (you, your date and two other matched couples with similar interests), two-person dates or large group activities, but only after a personal interview with DeSoto and 11 pages of questions about you and your ideal mate. Some questions–"How would you spend a beautiful day?"–seemed benign. Other questions were touchier, but equally or more necessary, such as, "How has your sexuality changed over the years?" This service was much more extensive and expensive, but I had a feeling it would be worth it.

As a trial member wanting two-person dates, I got three custom matches from DeSoto, all good for me, in her opinion, but still ranked according to overall compatibility. I first went with "Kate," my No. 2, to dinner at Café Sistina and drinks at Bar 35. Right away I appreciated just how much DeSoto had worked, as the conversation and laughter came easily and I ended up having a good time. Same for the dinner another night with No. 3, "Sabrina," at Mekong. But, DeSoto kept telling me, "Wait until you meet Cora."

My top-ranked match, Corazón (her real name) and I talked just once by phone and agreed to meet at E&O Trading Co. for dinner. Smart, funny, sexy–in that order–is how I described my ideal woman, and from the indelible first moment I realized Cora had the last quality the same way Bill Gates has disposable income. The restaurant’s bright, colorful Southeast Asian decorations blurred to soft white, and it wasn’t long before Cora had me captivated for good, easily showing the first two qualities in spades, too. Four seamless hours of casual, but intimate, conversation later, we had agreed on a surf session, and a Friday night of drinks–as the start of things we’d like to do together in the near future.

The one thing that sticks out most in my mind after this month of dating adventure? DeSoto had told me Cora had lips like Angelina Jolie. She was right about that, too.