Last weekend, after 14 straight days of listening to nothing but “My Beautiful Dark Twisted Fantasy” in my truck (I’ve listened to “Hell of a Life” so many times that my girl’s now convinced I’m going to leave her for Lauren N. Woods), I reached into my armrest and blindly pulled out a cd; not caring what the hell I picked as long as it was something different.

I landed on 88-Keys’s “The Death of Adam” , a concept album telling the story of a young man (“Adam”) and his dating difficulties. From courtship to catching an std, each track wittily, humorously, and sometimes bitterly revolves around a different relationship related issue. (Also, if I were 88-Keys, I’d re-release the album next month. But, instead of calling it “The Death of Adam”, I’d re-title it “Wait, my album is 5 times better than B.O.B.’s. Where’s my f*cking Adidas commercial?“)

Track two, “Nice Guys Finish Last”, is particularly insightful, as Keys raps about courtship and chivalry while an uncredited voice sings “Be nice to her” in the background.

“…go the extra mile dog, open the door for her

that’s more points all on your scoreboard

and you can give her hard wood like a floor board…”

It’s no accident that Keys follows “Nice Guys Finish Last” with “The Friends Zone”, a song spelling out exactly what many men feel is the end result of being too nice and too accommodating to a woman. Whether 88-Keys is 100 percent accurate in this assertion is inconsequential; what matters is the fact that many men (and women) truly do feel that nice guys finish last, and these songs resonate because of this common belief.

From our books and our blogs to our cds and our conversations, the idea that nice guys are near the bottom of the sexual totem pole is deeply embedded in our culture. But, although I do think that too nice guys probably do have more dating difficulties than, um, “not too nice” guys, I wonder how much of this feeling is just perception and self-fulfilling prophecy. To expound, what exactly do nice guys do (or not do) that gives them (and us) the idea that they’re destined for desert d*ck? And, do the nice guys who have dating difficulties have them because they’re “nice”, or are they subtly self-sabotaging themselves and using niceness as a scapegoat?

***Note: This post isn’t addressing “nice” guys in general, but nice guys who always seem to struggle with romance***

1. They tend to fight outside of their weight class

While I wouldn’t just come out and tell someone they’re pursuing women so far out of their league that the only realistic endpoint options are “friend’s zone” and “restraining order”, a problem I’ve seen with many self-proclaimed nice guys is that they pursue women so far out of their league that the only realistic endpoint options are “friends zone” and “restraining order”.

Thing is, while “out of his league” is usually cited when referring to aesthetically belligerent men attempting to holler at Beharies, in this context, “out of his league” describes what happens when a relatively inexperienced and sexually naive man puts all his eggs in a “she’s a bit too grown for you, dog” basket. They’re just not ready for the type of woman they’re interested in.

Basically, they’re flyweights (unsuccessfully) trying to get in the ring with heavyweights, not realizing that not being allowed to fight is actually for his own safety.

2. They tend to overestimate what everyone else is doing, and they blame what they’re not doing on their “niceness”

This isn’t just a nice guy issue, by the way. Even in yesterday’s entry, there were a few comments from women who assumed that pretty much every 25 to 30 year old man had at least 25 to 30 sexual partners; not realizing that only a small percentage of men reach those types of numbers.

Nice guys tend to take this to an extreme, though, occasionally adopting a self-defeating mindset based on the assumption that everyone is experiencing all these orgasmic experiences except for them; a blue-balls breeding state of mind that usually leads to bitterness and pay porn site subscriptions.

3. They waste too much time with people clearly not interested in them

Getting caught in the friend’s zone and staying there is (somewhat) acceptable when you’re still in high school or college. You’re young, (relatively) inexperienced, and you sometimes can’t help but get caught up if circumstance dictates that you’ll see many of the same people over and over again.

But, once you’ve graduated—or, if you’re a black male, “once you’ve dropped-out“—there’s no excuse to spend an entire weekend rubbing the shoulders and combing the scalp of some janky chick you’ve developed an unreciprocated infatuation for; watching her walk around her apartment in her pajamas while you blue-ball yourself with the distant hope that, one day, she might let you sniff her panties.

4.They don’t establish themselves as sexual beings

While it’s probably not the best idea to just pull out your wang and place it on the bar stool as soon as you meet someone, a subtle difference separating most “nice guys who struggle with dating” and “guy who have sex with women” is the fact that the guys who have sex with women don’t hide the fact that they’re interested in having sex with women. It’s not necessarily an overt acknowledgment either, as much as it’s just them letting a woman immediately know that they’re not really that interested in just being “cool”.

5. They tend to fall in love with ideas instead of actual people

Full disclosure: A decade or so ago, I was completely infatuated with a “friend” of mine, so infatuated that I actually did each of the four things I just listed. (Yes, even the weekend shoulder rubbing. I was still in college, though, so you can’t hold this against me)

Thing is, a couple pointed conversations and timely events made me realize that I was more into the idea of her possibly being into me than I was into her. I didn’t want her, I just wanted someone like her to want me; a state of mind leaving me stuck on a mental and emotional investment for someone I really wasn’t even all that attracted to. Basically, I wanted–needed— her to validate me. And, as you can imagine, she wasn’t particularly interested in doing that.

After talking to a couple “nice guy” friends of mine, it seems like they tend to get caught up in the same predicament; so focused on potential and possible progress that they lose sight of actual people and personalities.

6. They have a faulty definition of “finishing”

Put it this way: If you call yourself a nice guy, and you’re sore that you’re not able to perpetually procure random panties, maybe you’re not as nice as you claim to be.

—The Champ