I didn’t buy my first car until I was 19 years-old, a 1986 BMW 325i with chipped paint, a bad clutch, bald tires and O.C.’s Word…Life permanently stuck in the tape-deck. Prior to that, I was a ride-bummer, public transportation supporter and a mom’s car-borrower. Beyond fancy footwork, and a whole lot of would-be gas money that went to crate filling, this era taught me a lot. One leading value still remains with me today.

Earlier this week, I was reminiscing how I used to time my walks to high school every morning to try to land certain rides en route. There was one particular female with some incredible – wheels, that I always favored high and above the others. The attraction was birthed in the physical, but I will never forget the morning she scooped me up one particular blustery northeast day, and invited me into her immaculately maintained SUV with the fog lights running, volume on 10 and that smell of Clinique Happy in the air. I felt like Birdie in Above The Rim, getting driven by the baddest B to Rucker, only I was headed to remedial math, and it was in the outskirts – of Pittsburgh. Nonetheless, I climbed in to find this outstanding young lady playing one of my favorite mixtapes, Brainfreeze, a compilation of rare grooves on 45, spun on four turntables by DJ Shadow and Cut Chemist in the late ‘90s. I was smitten. A pretty girl, with dusty fingers and a library of audiophile knowledge predating the iPod, and your boy was ready to pawn his Technics and record collection for a ring and say “I Choose You.”

As fate would have it, it never worked. Moves were made, words were said, actions were taken, but the exchanges were a one-off like a MF Doom record contract. No proverbial great music was made – I had to let her pass.

As a man who makes his living in the Hip Hop industry, I’m often expected, if not told – that my best match is Bonita Applebum herself. I used to agree, sizing up every beautiful woman in the front row of every Hip Hop show, who inevitably either ends up getting rosy in the green room with the performer, or quite respectably cares more about a quality concert than legions of sweating b-boys trying to grope with the hand they’re not passing demos and flyers with. My first date, first question was music-based, and I judged a woman not on her character, but on her play-list.

In looking for the perfect b-girl, I’ve made plenty of mistakes. There was a parking garage session to Cam’ron’s first album in a Mercury belonging to a woman whose name escapes me. There was a college student standing next to me who knew every word to Common’s “The 6th Sense,” who shortly thereafter, I bailed on. There was that young lady who adored me for having a Stankonia advance three months early, but seemed to hate me when “Gasoline Dreams” wasn’t playing. I can go upward and onward, but my grandfather always said to keep politics, sex and money under wraps. By no means a womanizer, I’ve simply pulled the plug with all of these Hip Hop honies at various points, because music and sneakers only gets you so far.

These days, I’m left curious about inner-Hip Hop dating. Almost 20 years ago, KRS-One and Ms. Melody were the Hip Hop couple, along with Herbie Azor and Salt, matched by Treach and Pepa or G. Rap and Ma Barker. I feel that since Wyclef and Lauryn went wrong, Hip Hop has just flat out known better. From ‘Pac and Madonna, Dr. Dre and Michel’le, Ad Rock and Ione Sky to Jay-Z and Beyonce and Common and Erykah, we just know better. Date outside of the genre, if not medium. It keeps things more interesting, better compatible.

I’m of a similar belief than these rap celebrities and short-lived power-couples. While I will admit that’s it’s been difficult throughout the years, as I’ve found my best matches in White Stripes, Tower of Power and Rihanna fans. I’m left to believe that there’s a missing link in harmony within Hip Hop for the sexes.

Hip Hop has a togetherness within its culture. I heard accounts of this after Rock The Bells, and I certainly have felt it myself at open mics, on the Broad Street Line here in Philly and at conversations at record stores flipping through plates. I love that fraternity (and sorority) of Hip Hop. Still, it’s something that I’ve written off seeking for my private life.

I have written off the notion of finding my soul-mate who loves De La Soul Is Dead as much as I do, or who encourages me to hang my framed Gang Starr Hard To Earn poster anywhere besides my office. I am left looking into other genres for my love, in hopes that Paula Abdul was right, and opposites are the best attraction. Hip Hop though, plays a difficult card for that. As b-boys, heads, call us what you will, we’re expected to be a certain kind of way, in search of a certain kind of thing, and while it’s not all wrong, it’s not all right, and it’s certainly not all good. Continued on page 2 »