Advice For My Teenage Brother: Do Nice Guys Finish Last?


Advice For My Teenage Brother is a column where I give advice to my teenage brother who is 17 years my junior. Unbound by any parental obligations to shape his mind a particular way or financially account for any of his mistakes, I can flex my brotherly instinct and tell him things things I had to learn the hard way. Perhaps the teens in your life could use the advice too.

“Nice guys finish last.”

We hear it so often, it’s become more proclamation than opinion. So much so that many of us just take as fact whenever Drake or Hopsin mentions it on a track, or when we mutter it to ourselves when we see some guy we don’t like with some girl we do. Culturally, it seems we think it’s less farfetched when a man makes a flying suit of armor in a cave than when some nice guy actually finishes a movie hugged up with the object of his affection. The former is superhero action. The latter is Hollywood fairytale nonsense. Probably because the nice guy must first beat up kids who have been doing karate way longer than him or take on gangsters with a magical Loki mask. The notion that nice guys finish last is so ingrained that a nice guy hero generally needs magic or insane luck to win at all. So we all understand what it means and how it works in our cutlure, but is it true? Do nice guys finish last?


Getting the Girl, Earning a Vagina?

First, we have to address the gross nature of this entire conversation. Feminism can be difficult for anyone to grasp, but it is particularly hard for a 16-year-old boy surrounded by other 16-year-old boys with 24 hour access to Reddit.

So let’s break down a few things:

We reside in a “rape culture” in which our society’s attitudes (and by extension our own) trivialize rape, deny its causes, regularly engage in things like sexual objectification, victim blaming, and the normalizing of problematic behavior. While “rape culture” is often about the attitudes toward women, the freakin President had to come out against the trivializing of prison rape recently. Does any of this seem heavy? Great! It means your soul is still intact.

There is a great deal of problematic, skeevy shorthand used when discussing dating and relationships, and language does affect our thoughts and reinforce our beliefs. For instance, can someone “deserve” sex or affection? Should someone be able to “get the girl” by saying or doing the “right things?” Can someone really “win” a person, or has the 14th Amendment put a stop to such things in the US?

Even a cursory glance at popular culture showcases how easy it is to turn women into objects with no agency of their own. They can be portrayed as vaginas to be fought over, polished, and placed on a mantle. It’s also very easy to trivialize men (and women) by lumping them into arbitrary categories such as “nice,” “good,” and “bad?” Therefore, if we want to know whether nice guys finish last, we need to understand what a “nice guy” is in a first place.

What is “Nice” Really?

Being “nice” is one step above invisible and one step below inconsequential. “Nice” is a sort of uncomfortable shirt that at least doesn’t make you look fat. “Nice” is what we call people we don’t hate, but hope we don’t have to spend time with. “Nice” is the language of politicians and PR reps. “Nice” keeps you employed but never gets you a promotion. “Nice” is the first thing neighbors say about a mass shooter because pre-condemning him or being too nice would make them irresponsible or affiliated. “Nice” keeps people at arm’s length.

When women say a guy is “nice,” they mean he has not exhibited enough positive characteristics to be considered as lover. After all, who wants to sleep with a mass shooter? I’m not saying that “nice” is an insult, just that it is not an impression. So whenever you see “nice” guys roaming the halls, screeching about the injustice they face at the hands of these women who get everything handed to them and refuse to see the sweet, kind hearted, and generous man right in front of their eyes, feel free to roll your eyes. But then help that man learn to express himself before he goes nuts someday from psycho sexual build up.

In the context of dating, The Nice Guy is all about attempting to get everything he wants without actually having to ask for it. The Nice Guy is often afraid of rejection to the point of catatonia or has adopted the belief that gaining a sort of “friendship” status in a woman’s life will lead to a stronger relationship with her. However, he takes no risks in that direction and never voices his feelings.

As a result, Nice Guys often find themselves in subservient roles to women in their lives. He’s “the friend who drops everything,” “the shoulder to cry on,” “the only one she can be herself around,” or “one of the few guys her boyfriend lets her hang out with.” Ouch.

Being nice in this context is not the same as being affable or kind, or generous, or attentive, or even a good friend. Being nice is lying in wait and simulating those attributes in the hopes that a woman will randomly decided to have sex with this person. It’d have to be random, because this sort of nice guy would never give her the option to choose whether she wants to or not.

The Origin of Finishing Last

Legend has it that “Nice guys finish last” is actually attributed to Brooklyn Dodgers manager Leo “the Lip” Durocher in 1946. It actually went down like this:

“Nice guys! Look over there. Do you know a nicer guy than Mel Ott? Or any of the other Giants? Why, they’re the nicest guys in the world! And where are they? In seventh place! Nice guys! I’m not a nice guy – and I’m in first place.” After pacing up and down the visitors’ dugout, the Dodger manager waved a hand toward the Giants’ dugout and repeated, “The nice guys are all over there, in seventh place.”


Leo the Lip. Surprisingly not a racist name for a Black ball player.


Later, it was shortened to the catchier “Nice guys finish last” and became the title of Leo the Lip’s autobiography. Like all great sports quotes, it easily translates from sports to advice on cocksmanship. Considering that whole “rape culture” thing allows society to see women as property or beasts to challenge and slay, it’s easy to apply sports quotes to how one should wield his male genitalia. The following are a few examples (For extra credit, add “in bed” to any of them):

“If you can’t outplay them, outwork them.”– Ben Hogan

“You’re never a loser until you quit trying.”– Mike Ditka

“The difference between the impossible and the possible lies in a person’s determination. – Tommy Lasorda

“If you aren’t going all the way, why go at all?” – Joe Namath

“If you train hard, you’ll not only be hard, you’ll be hard to beat.”– Herschel Walker

And my personal favorite:

“Everybody has a plan until they get punched in the face” – Batman Mike Tyson

“Nice guys finish last” is actually about winning pennants, but these days “finishing last” is all about… what exactly? Losing at women? Losing at life? I mean, one could make the argument that finishing at all is far better than not competing. Oh that’s right… Wayne Gretzky did that already when he said, “You miss 100% of the shots you don’t take (in bed).”

I propose that “finishing last” is about not living up to your potential, which is bad because TV tells me it’s bad all the time. This is an unfortunate outlook because failing repeatedly is actually the only way to learn how to be proficient at anything. I’m sorry Drake, but not all of us are blessed to be great at things the first time we try them like SOME people.

Nice Guy + Finishing Last = ???

So “being nice” is all about being noticed without being inoffensive, useful without being invaluable, and kind without honor. For our purposes, let’s say “finishing last” means “not winning hard enough to get laid or be loved by anyone because all the quality vaginas will be taken by all the winners and the winners are ostensibly not nice.” God that’s bleak. It’s also bullshit.

What the The Nice Guy fails to understand is that he suffers from a lack of honesty about his own feelings. Rather than expressing himself openly and succinctly, he engages in a sort of relationship gamification. If he can complete enough quests or acts of kindness, then the female character’s love meter will eventually get high enough where she will reciprocate his feelings. It’s bad enough that that’s how actual games treat relationships, but they’re only making interactive versions of what we see in movies – more Hollywood fairy tale nonsense. Win the big game or she’ll never love you. Beat her boyfriend in the big race or she’ll never love you. Save her from the Death Star or she’ll never love you.

This notion of nice guys finishing last is easy to frame romantically,  but I believe it goes beyond just sex and romance. The Nice Guy takes the same approach with his parents, his teachers, his bosses, his coaches, and his friends. He gets used to putting the needs of others so far above his own that he spends most of his life empty and spiritually starving. It’s often not until illness and depression consumes him that he makes any lasting changes to his life. A “Nice Guy” is really a euphemism for “insecure person,” and a world full of narcissists has a desire to devour such a person regardless of gender, status, ability, or cocksmanship.

Do Nice Guys Finish Last?

Little Brother, I have spent much my life as a consummate Nice Guy. I followed women around, remained available for them and did stupid favors when I could have just asked them out and moved on. I became a “friend” instead of a friend and passed on amazing opportunities with amazing people because I was too afraid of being wrong and getting embarrassed. I spent a lifetime with putting other people first, then being salty about it when the let me.

Rather than seeing this insecurity for what it is, we often point at our desire to be kind, affable, etc as the reason we aren’t taken seriously. In reality, Nice Guys don’t take ourselves seriously enough in the first place. We think that the solution is to be more like the assholes and bullies we dislike/envy, missing the obvious fact the only thing they have over people like us is their and willingness to ask for what they want without reservation.

So the real question isn’t whether or not “nice guys finish last,” but whether “insecure people can get what they want without asking for it.” Naturally, the answer is “sometimes,” but if insecure people can learn how to be authentic, and speak up on their own behalf, and handle rejection appropriately, they’ll get what they want a lot more often.



Michael Bridgett

Writer, vocalist, lyricist and raconteur. In other words, the guy everyone really loved at the party. I traffic in things geek, existential, fun and funny. I believe that it is the compassionate sharing of ideas that will lead us to a new age. An age in which all benefit no matter who we are, where we are, or what we want. We must allow ourselves to grow beyond tribal concerns as the fate of everything is at stake. What we do here gets us one bit closer every day.

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