I've been happily single in the city for a while now, so when my recently engaged younger sister asked, "Are you going to have a boyfriend by my wedding?" I was a little shocked. Surely at 25 I had a few good years of unfettered fun left before settling down? While my high school classmates have babies and buy houses, I'm happy with my go-it-alone cosmopolitan existence.
Still, the wedding. I took my sister's point that my unmarried state didn't mean I had to show up dateless. Perhaps I could "put myself out there" more. But what does that mean, exactly? It may sound like an excuse, but my dating downturn isn't all my fault. I've waded through sea after sea of pleated khakis, and all it has done is left me wondering where all the plain-front fish are. What I needed was a little advice.
Enter Dave Singleton, whose book "Behind Every Great Woman Is a Fabulous Gay Man" is the latest helpful read for any SPF ISO SPM. Now, whether from my grandma or Dr. Drew, third party interference in matters of the heart is not for me. After all, keeping track of the advice can drive a woman crazy. In my years of dating, I'd broken the Rules, fouled out of the Game, and OD'd on Savage Love.
But since the book jacket touts Singleton as better than Ann Landers, Carrie Bradshaw and Dr. Phil combined, I had high hopes he'd leave me better off than reading "He's Just Not That Into You."
But who is this Singleton (yes, it's an ironic name for a relationship adviser) and what makes him such an expert? As the author of "The Mandates: 25 Real Rules for Successful Gay Dating" and as a columnist for Match.com, the 44-year-old Washingtonian has long been advising gay men on their love lives. And after playing Will to countless Graces over the last 20 years, Singleton says he decided to write the book as a valentine to all his single girlfriends. Only a gay boyfriend, he argues, can provide the tough love without an agenda -- something I agreed was rare, even from your closest girlfriends.
After reading his book, I caught up with Singleton for cocktails -- and advice -- at Local 16. To help him pinpoint my repetitive fatal dating flaw, I recounted all my like, lust, love and loss stories -- from my first boyfriend who kept me out too late and drove my parents crazy to the good-on-paper guy in college, a Harvard class president. Too bad his idea of courtship was gazing into my eyes across Baked Lays at Subway.
Subsequent stints included men too old, too serious, too intense -- always too something. Singleton listened carefully and in less than 30 minutes dubbed me part "Miss Defensive" and part "Miss Overly Critical." Whoa. Am I completely transparent or is he really that good? I definitely have a tendency to come off as independent to a fault, but was I really overly critical of my suitors?
Singleton pointed out that I can keep my high standards, but shouldn't be so quick to shoot down every man who can't meet them. He advised me to open my mind, view dating more as a numbers game and perhaps discover I enjoy some of the guys who initially didn't "measure up." After deciding the cutest guy in the place was behind the bar, I left feeling a bit more conscious of my dating self.
So how has Singleton's advice played out in my dating world? I've given that critical eye a vacation (though it still raises an eyebrow on occasion), and I am working on that overly independent thing. His common sense recommendations may not be groundbreaking, but we've been so bombarded with guides to hunting, fishing and hooking men that suggesting an even-keeled approach to relationships is a fresh idea. If you already have a gay boyfriend, you probably won't need Singleton by your side. If, however, you've found yourself crazed, burnt out or discouraged by the dating universe and have no males to help you navigate the choppy water, his bright yellow book can serve you well.
As for my sister's wedding, I've got some time so I don't have to throw myself on the mercy of the online gods yet (Dave is a big advocate of online dating). I'm not quite there. I need meeting people to be more organic -- even if it is three martinis into happy hour. Still, I'll keep the book in plain sight as a reminder that it's all a numbers game. I guess I'm still critical, but at least now I'll have a fabulous gay angel on my shoulder reminding me to give the guy in pleats a chance. Maybe.