You can’t always get the girl. The run-its-course concept of “he’s just not that into you” became a full-blown cultural meme after a 2003 Sex and the City episode inspired the bestselling self-help book and an all-star Hollywood movie. But men are typically more goal-oriented: When she’s just not that into you, fellas sometimes handle it a little differently. The challenge alone of wooing a woman can start to overshadow what put that challenge into play to begin with: the attraction.

Take the case of “Chastity,” a college girl I met on the 6 train to the Bronx one summer afternoon way back when. An aspiring singer-actress, she worked retail at an Emilio Cavallini boutique downtown, with dreams of rocking the same spot that double-threats like Grammy-/Oscar-winner Jennifer Hudson eventually held down. An almond-complexioned cutie with faintly Asian eyes and braids shades of Poetic Justice-era Janet Jackson, Chastity was the first artist I ever dated. Half of the turn-on came from watching her strategically manifest her dreams.

Hip-hop journalism barely existed outside of Word Up! magazine at the time; I had no idea I’d end up interviewing celebs for a living. Chastity was inspiring. A Fame-school graduate from LaGuardia High School of Music & Art and Performing Arts—classmates with Marlon Wayans, Omar Epps, and others—Chastity already knew exactly what she wanted and ran it down by any means necessary. She appeared in rap videos like Young MC’s “Bust a Move,” and later formed a female R&B trio called Ariél. They flopped hard (“Do the Boodiewop” anyone?), but no matter. I wanted to see just how chaste Chastity really was, and the longer the chase lasted, the grander the fantasy grew in my head.

Because the thing is, we never had sex.

I treated Chastity to the winter season of Alvin Ailey Dance Theater; I’d brought her to Black and Blue on Broadway; I took her to dinner at however many restaurants; I introduced her to singer Rachelle Ferrell, her idol; plus we’d seen Janet Jackson live in concert, twice. Somehow Chastity had me whipped and I’d never even seen her in her panties. My homeys were ashamed.

Eventually I got a regular girlfriend, naturally. I’d asked Chastity for a relationship early on, but she didn’t want a long-distance thing (I lived off-campus in Atlanta at the time), so she refused. I cheated on my college sweetheart with Chastity whenever I came up to New York City—I was young, dumb, and full of coming into my own as a young adult—but we never consummated the courtship. When she studied abroad at the École Normale de Musique, she invited me over to Paris for a visit, and that’s the farthest we ever got. I gave her an intense hot-oil massage and downtown lip service that lasted the entire 19 minutes of the Miles Davis blues, “Star People.” Still no dice.

Somewhere along the line, sleeping with Chastity stopped being about Chastity at all. From my immature point of view, I’d already invested beaucoup seduction time, and hung in there patiently above and beyond the call of duty. Our chemistry together was sitcom worthy, but I’d lost sight of whether or not Chastity was someone I really wanted to be with beyond the sex I felt was long overdue. I had hardheadedly rejected accepting her friend zone, though looking back, that’s obviously where she stuck me after the first few months of the relationship. She’d already said no to the bf-gf thing, and if I still wanted to bless her with all the benefits of being my girlfriend, far be it from her to ever stop the cycle.

And then I read Iyanla Vanzant’s In the Meantime. (Not to take a turn for the corny, but this was the ’90s after all.) The book gave me the idea that maybe I was feeding Chastity’s ego with this never-ending pursuit, that maybe I was more addicted to the cat-and-mouse game of it all than sincerely wanting to be with her, sexually or otherwise. Was she using me? Testing the theory, one day I decided to just stop calling her. Months elapsed. When Chastity finally reached out, she left a voicemail message about catching up…and could I do a favor for a girlfriend of hers? I called the girlfriend (a mutual acquaintance) and granted the favor. Chastity never called again.

And yet at 24 I used our whole unrequited love tryst as the basis for my first novel, Irrésistible. The manuscript—which I described as a Woody Allen tale with a Def Jam soundtrack—got me a lot of attention from urban magazine editors when I first started jockeying for lengthy feature stories. And I met my wife Christine through Chastity on that first trip to Paris. If we’d slept together, Chastity would probably be just a footnote in my lovelife. What’s clear is that she was ultimately meant to play a far different role.

Miles Marshall Lewis is a writer, editor and bohemian b-boy in New York City. Check him out on Facebook, follow him on Twitter:@furthermucker and visit his personal site

How much work are you willing to put in for a new relationship? How do we avoid chasing the wrong things in a new relationship? Sound off!