How familiar is the following scenario? You meet a wonderful woman, start to woo her… and then realize she’s hung up on an inarguable loser—one of those guys with a silly name (or nickname) who plays a guitar (not always well), seems to be too fucking cool for his own good and isn’t nearly as together, successful or caring as you are.

Is now the time to mention Jake had no car, no job and no place to live? Back then, this hardly seemed to matter. As I saw it, when you were as cool as Jake was, people clamored to drive you around or offer you a couch.

I know all about it because I was once so hung up on such a guy that for a long while, I ignored a bunch of other, far more appropriate men. This guy’s name was Jake, which is to say that his name wasn’t really Jake because I just don’t have it in me to use the real name of someone I’m calling out as a loser. I have a heart, people.

Jake, as it turned out, did not. What he did have, however, was an ability to charm me silly with his rough, take-no-prisoners swagger, a swagger I found difficult to explain when I was involved with him but later learned in therapy to describe with one simple word: narcissism.

People put such a pejorative label on narcissists, but the fact is they can often be incredibly charming. And back then I didn’t even think Jake was a narcissist. I was 22 and so I thought that Jake—with his longish, not-gelled hair, permanent cigarette attached to his lip and deep voice charred and scarred by all those smokes—was dreamy.

I’d never dated anyone like Jake before. I was a private school kid who’d really only dated other private school kids, albeit the more rebellious ones. Jake hadn’t bothered with school all that much and, though his mom had raised him, it really seemed more like LA had been his parent. He knew all the clubs, back alleys, tattoo parlors and people one should know—including a slew of celebrities, all of whom seemed to be trying to mimic the coolness that Jake just naturally projected.

Is now the time to mention that Jake had no car, no job and no place to live? Back then, this hardly seemed to matter. As I saw it, when you were as cool as Jake was, people clamored to drive you around or offer you a couch. I, for one, loved driving him to his acting auditions on those rare occasions when he had them and lived for the days and nights he spent at my place.

At first, she hangs on his every word…

But after a few months, Jake suddenly, without explanation or warning, disappeared from my life entirely. I was devastated, and since I was drunk a lot of the time back then, I’d do things like show up at 1 a.m. at the club where he was sometimes a promoter, asking the bouncer where he was and crying drunkenly on this often confused and uncomfortable bouncer’s shoulder about the way Jake had broken my heart. I even have a fuzzy and unfortunate memory of sharing, with permanent marker, my love for Jake on the club’s door. (Note to anyone out there pining away for someone: Don’t do this. Ever.)

Eventually, of course, I got over Jake and, years later, when I ran into him at a party, he casually explained to me why he’d had to make such a sudden and rash exit from my life: “You really needed to shave, baby,” he’d said, cigarette dangling from his lower lip. “Down there.”

Yep. That was the maturity level and depth of the guy who’d crushed me. It barely seemed worth asking why he hadn’t just told me the hair down there bothered him at the time. Pulling off a disappearing act sure seems like a hell of a lot more trouble than a conversation about waxing. But what do I know? I’m not one of these guys.

Which brings us to the real question: What was it about Jake—a man with no job, education, aspirations, common decency or respect for women—that drove me so crazy?

Eventually, she comes to her senses…

I loved that he didn’t seem to give a shit about what anyone thought of him. I loved that he behaved exactly the same wherever he was, whether we were at a stuffy cocktail party or raucous after-party. I loved that he seemed to have the courage I only wished I had to say, “Screw you” to the world’s expectations and not try to succeed and belong the way society tells us we need to. In other words, a lot of the things that made him, technically, a loser appeared nearly heroic to me. That—and the fact that I thought he was super hot—was all it took to turn me into a permanent marker-clutching mess.

Thing is, I’m hardly the only woman to get hung up on this kind of guy. Amy Dresner, a writer in LA with long legs and a biting sense of humor, says, “I once fell for a guy who was so broke that I paid for cigarettes, gas, food—everything. And since he asked me to watch his place when he went away and his water got turned off, I had to pay his water bill, too.”

What had her continuing to open her wallet? “He was super charismatic, smart, hilarious, stylish, had a big dick and treated me like shit,” she responds matter-of-factly. “I think it appeals to my genuine, deep-seeded insecurity. I feel like if I can just get this guy to like me, I’ll have triumphed and can feel good about myself. The emotionally unavailable guys keep me on my toes. They keep me hoping, excited, challenged.”

And the worst part according to Dresner, is that financially supporting these guys always backfires. “At some point they start to feel emasculated and resentful, since men get so much of their self-esteem from having and making money.”

It was Nate who forced Alex to realize why these men drew her in. “I saw then that when a man is broken, it makes me feel really useful to try to fix him…”

Alex Wilkins, a law clerk from London, noticed the same thing. When she first met her unemployed charmer, he seemed to be the opposite of emasculated: well educated and funny, Nate told her he was a successful comedian who was on the verge of becoming a household name. It was only when they’d been seeing each other for a few weeks that Alex realized Nate never worked at all and just made up all the gigs he told her he was doing. “One evening I met up with him at a bar after what he’d told me was a really big comedy job at a nearby venue,” she recalls. “Later, when he went to the loo, a casual conversation I had with the barman revealed that he’d actually been at this bar all night long, just drinking.”

Nate wasn’t the first semi-tragic guy Alex had dated. There was also a guy who “used to hang around the footballers at Queens Park Rangers and wear the QPR shirt in the hope that people would mistake him for a player” and the boyfriend who needed her to speak to his boss about a pay raise because he was too scared to ask for one himself.

But it was Nate who forced Alex to realize why these men drew her in. “I saw then that when a man is broken, it makes me feel really useful to try to fix him,” she admits. “I start to feel very important and special—like I alone hold the key to solving his problems. But I think I also felt, on some level, that if I fixed them, they’d never leave me.” Turns out that this wasn’t so much a Faustian bargain as it was a fruitless one. “Not once did any of these men thank me—or even ask me how I was doing or what was going on with me,” she says now.

And he’s left alone with his cigarette. (Unless, of course, he’s Ryan Gosling.)

Looking back, Jake was never much for asking me how I was doing or what was going on with me, either. And it was pretty much the same story when I ran into him recently, too. The years hadn’t been kind: he was in rehab for the umpteenth time and still had the cigarette attached to his lower lip, but it wasn’t as sexy at 40 as it had seemed at 22. And I guess that’s the ultimate takeaway about the loser guys who seem able to win a lot of women’s hearts. They’re sort of like the high school football players that everyone thinks will rule the world but instead end up dropping out of college to not amounting to a whole helluva lot. Never growing up gets pretty old for those of us interested in continuing to grow.

And speaking of growing (or not), a few years ago I had my bikini area lasered. I’m happy to say this decision had nothing to do with Jake.