Why (Some) Nice Guys Finish Last

If you’ve ever seen a “chick flick,” “rom com,” or whatever term you deem for a romantic comedy aggressively targeted at women, you’ll often find, in addition to the ludicrous career choices for women (shoe designer, fashion designer, baker, editor at a magazine, handbag designer, you get my drift…), a designated “nice guy” who gets friend-zoned by everyone, including our heroine du jour. Until, of course, a series of misunderstandings and maneuverings land him in bed with the heroine until she ends up with the standoffish but muscular Mr. Right, or (gasp) our Nice Guy ends up being the hero. Wow! Did anyone see that coming???

Okay, so unless that previous paragraph was not enough evidence for you, I admit that I mostly hate chick movies. I have my select few that I adore (apart from my Jane Austen period films, which I don’t count, because they far outstrip most chick flicks). I could pull apart the many tropes that I detest, but I’d like to include one that transcends the chick flick and actually has been seen in other entertainment genres, as well as real life. Ladies and gentleman, I’d like to talk today about the Nice Guy.

We’ve all encountered him at one point. He’s a seemingly decent fellow, stable, dependable, etc, who just can’t seem to “get” the girl of his dreams. Now, by “get,” I don’t mean understand (because if we really understood the objects of our fantasies, they would stop being the objects of our fantasies, amirite?), but rather obtain, win over, other adjectives that imply a he-man conquering of the she-lady. He bemoans to his friends, male and female, “Why doesn’t anybody like me? I’m a nice guy!” And sometimes, he is able to have a relationship, sometimes with the object of his desire. And some women oooh and awww over what.a.nice.guy he is, and wonder why nobody dates him. But yet, their lack of interest in dating him should set off signals about the Nice Guy.

I know a lot more single women than I do single men. It’s a strange phenomenon, really. But for whatever reason, I know lots of great, attractive, professionally successful women who are single and unattached. Not so many guys, however; it seems that when a nice, eligible man is “on the market” so to speak, he finds a partner relatively quickly. My personal theory somewhat dovetails with the pilot episode of Sex and the City, in which the women wonder why there are tons of great single women and not tons of great single men. Miranda Hobbes’ theory is that the [insert undesirable adjective] guys are just as ungrateful and demanding as the hot jerks.

MirandaWhile that is a bit cynical for my taste, she makes an interesting point. The world is not simply made up of hot eligible bachelors and ugly jerks. Rather, those qualities are interchangeable, and we are not promised a fairytale ending. What I also find interesting about this observation is that there’s a subset of guy who’s not necessarily falling over himself to date a beautiful woman—he puts that impression out there, but may be just as selfish and ungrateful as the man who can by society’s standards more legitimately think highly of himself. And that brings me to the Nice Guy phenemonen.

You see, while a Nice Guy puts himself out there as the alternative to the Hot Jerk, he’s not really a nice guy for the sake of it. No, it’s a carefully constructed act, one that makes him seem desirable and attractive, particularly to catch the eye of a woman he’s lusting after. In other cases, he suffers from incredible moral superiority until the stank of his holier-than-thou act drives him away from sane and reasonable people with normal flaws and quirks. In this way, the Nice Guy differs from his counterpart, the Gentleman, a man who is friends with women, and who may just want to date someone, but is actually a great friend.

For example, let’s look at everyone’s favorite Friend, Chandler Bing. Yes, Rachel was the prettiest, yes, Joey and Phoebe were funny, yes, Monica was neurotic, yes, we all HATED ROSS, but Chandler is a cool guy who ultimately stole all our hearts. Why is that?

First of all, when Friends began, we all saw Chandler as a loveable, nerdy loser who could never say the right thing to a woman he wanted to sleep with (unless, of course, that person happened to be Janice).


Thankfully, Chandler demonstrated a quick wit and an acute self-awareness that transformed from awkward to endearing as the years passed. If he was desperate, he didn’t hide behind a façade of what a great guy he was—rather, his painful honesty made him a relatable figure to those of us who watched.


And then, when Chandler hooked up with Monica, one of his best friends, he worried that dating would ruin their friendship. Thankfully, their ability to laugh at themselves—and each other—plus a sense of who they were kept them from the “We were on a break!” roller coaster of Ross and Rachel.

Not all Nice Guys are Chandlers, unfortunately. There are varying degrees of Nice Guy, but the three I’m going to talk about today irk me for very specific reasons. Obviously, this is very biased, so feel free to add your own changes or suggestions in the comments.

Bachelor #1 for me would have to be…Aidan Shaw of Sex and the City. Yes, I chose Aidan. I can’t stand that guy. Years before I started watching the show, I heard tons of female acquaintances oohing and ahhing over Aidan, and what a great boyfriend he was. I will admit, Aidan has redeeming qualities, several more than many of the other guys Carrie Bradshaw dated. Aidan often seems like a fairytale, when compared to the alternative.


Although, in the words of Pitch Perfect’s Fat Amy:


I spent a lot of time during Sex and the City wanting to punch either Mr. Big or Carrie Bradshaw in the face, depending on whose level of selfishness was greater. And that alternated constantly.

Ahem. Back to Aidan. When compared to the iceberg that is Mr. Big, Aidan seems like The Perfect Boyfriend. He is a furniture designer with a dog and quirky long hair and jewelry. He genuinely wants to be with Carrie. But here’s the problem: it’s a certain kind of Carrie that she puts forth and he lets himself believe is the real Carrie. To develop this analysis a bit further, I need to split Aidan into his Season 3 and Season 4 incarnations, because there are some interesting shifts that may prove my point about his being a Nice Guy in the end.

Season 3’s Aidan is portrayed as an Aw-Shucks kind of guy with the hair and wardrobe to match.


Charmed by Carrie’s deceit at being a designer so she can buy his expensive chair, he asks her out—but only if she’s a non-smoker (to his credit, he is upfront about his dealbreakers). Carrie panics and lies that she doesn’t really smoke. And Aidan chooses to believe this. Dude. A woman who is pulling out a cigarette during a casual conversation is not a casual smoker. Politely make your excuses and leave. But no. Aidan does later catch Carrie sneaking a smoke on their date and gravely notes that they have a problem. At the end of the episode, we see Carrie sticking on a nicotine patch, musing that she hopes he’s worth it.

To add to that, he likes the country and he has a dog, while Carrie is a fashionista who likes herself. A lot. She also ends up having an affair with Mr. Big, so there’s that. Her nervous, jumpy behavior should give Aidan the hint that All Is Not Well. Of course, when he finds out that not only has Carrie been smoking but cheating on him, he ends the relationship for very valid reasons.

Enter Season 4 Aidan. He knows how he feels—angry and hurt. Yet, he hooks up with Carrie and agrees to try their relationship again. Let’s also note that Season 4’s Aidan has been upgraded to better clothes, better hair, and a lither physique:


But there’s a particular episode when he and Carrie have moved in together in which he treats her terribly. He slaps on a nicotine patch and makes all sorts of crazy gestures when he hears a voicemail Mr. Big has left. Now, mind you, Aidan has every right to be upset that Carrie was unfaithful. But if he’s still upset, he needs to not be dating her. He can’t be living the past if he’s willing to try out the future again. Carrie is not at all blameless in this story arc, but I don’t want to go there at this point. The point is: Aidan should never have signed off on a relationship he still had doubts about. End of story. And that’s why I was never Team Aidan. Knowing better and still choosing poorly does not make you Mr. Right.

Let’s move on to Exhibit 2, shall we? Meet Ross Geller. Yes, I realize he’s kind of an easy target. Nevertheless, the showrunners poised him to be the hero in Friends without fully realizing that in the end, it would be the prettiness of Jennifer Aniston (because she wasn’t really able to exercise her comic talents until Horrible Bosses, lesbihonest) and the wit and charm of Matthew Perry that would make the show an enduring hit.

But seriously, folks, Ross Geller is kind of a boob.


The first season finds him wondering why his wife left him (answer: she’s a lesbian and he did not read the numerous signs). And then, his high school infatuation, Rachel Greene, walks back into his life, having run out on her own wedding. And for the entire first season and a half of Friends, we get to witness the delightful tango of Nice Guy pursue Object of Desire. Ross does things for Rachel, but Rachel doesn’t realize it’s a ploy for her to respond to Ross’s overtures with gratitude sex. Unlike Chandler, who listened and sympathized with Monica’s problems with no other expectation of return than the bounds of friendship would ask, Ross schemed to excite Rachel’s gratitude as a means of awakening her desire for him. Eventually, it actually worked.

And then Ross has to Schrute the whole thing up. To be fair, though Rachel is not blameless, either. During a really huge fight, in which their relationship kind of seemed to be ended, Ross had revenge sex with the girl who worked at Kinko’s (or some other post office/copy shop of sorts). When Rachel wanted to patch things up, he guiltily and uneasily agreed. Of course, Rachel found out about the copy girl, and accused Ross of cheating on her. And this  is where his iconic reply comes in:


Yes, instead of admitting that he might have been a pre-emptive schmuck and misunderstood their fight, Ross defends himself and throws his own mistake back in Rachel’s face. Way to go, guy.

Of course, Ross spends the rest of the series trying to get back together with Rachel, and there’s all sorts of back-and-forth shenangians that wore us all out by the time the show ended. I never forgave Ross for being a manipulative jerk in the guise of a nice guy. Also, never forget the spray-tan incident.



It’s time to move on to Guy #3, the one who inspired this post in the first place. Leonard Hofstadter, I’m looking at you. I can’t stand you, dude.


Don’t look at me like that. You know what you’ve done. Leonard, in my eyes, is the perfect trope of Nice Guy. He does all sorts of boyfriend-y and friend-y things for new neighbor Penny, including getting her TV back from her old apartment and facing down her ex-boyfriend, being nice and listening to her many, many guy problems, inviting her over to eat dinner with the guys and switching out one of their routine dinners-out to the Cheesecake Factory, her place of employment.

But are Leonard’s motives innocent? I argue no. Because there are subtle moments when Leonard acts out his resentment that Penny is not eager to go out with him, especially when he can’t seem to work up the nerve to ask her out. He behaves passive-aggressively, especially when Penny obliviously accepts his gestures as markers of friendship—which on the surface they seem to be!

Leonard: if she’s not responding to your boyfriend gestures by becoming your girlfriend, then she’s just not that into you. By now, Leonard and Penny have gotten together and broken up and gotten back together again. But I just can’t seem to get past Leonard’s whiney, mopey, douchey behaviors.

On a separate note: Ladies. Do not feed the bad behaviors! If a guy is constantly offering to do amazing things for you, pause. Ask yourself, “Is he just a great friend, or is he trying to get out of the Friend Zone?” Beware. It can be a fine line. If you think there might be strings attached, do not take up those offers. Don’t take advantage of a Nice Guy just because he offers himself up. You will find yourself in an endless loop of obligations and resentment and regret and drama. And no one wants that.

Guys: don’t think that acting as a friend to enchant a woman is going to instantly win you relationships. Be a friend first. If you are at all a decent fellow for no other reason than being a friend, chances are some lady’s going to notice and reciprocate. Remember: we all liked Chandler better than Ross, because Chandler liked his friends and Ross liked himself.



Filed under Celebrity, Culture, Friendship, Outlook, Television

2 responses to “Why (Some) Nice Guys Finish Last

  1. Anon

    On a related note, the concept of the dreaded “Friend Zone” makes me gnash my teeth in rage. The concept is that a man is nice to a woman with the hope of having sex with her and she only wants to be friends with him. But when men act bummed about being “in the friend zone” what they are implying is that they were owed something for being nice. As if they deserve sex just for being a decent human being. As if friendship is something lower in value than a lousy lay. As if friendship is hardly worth anything, for that matter.
    Honestly, the wide availability of alcohol in this country guarantees that a person will always be able to find someone to have meaningless sex with them. But good friends? Are SO RARE. And guys who act nice only to get something in return are not Nice Guys, but Manipulative Jerks.

  2. Anon

    Also, I totally agree about Leonard Hofstadter. Even when he and Penny are portrayed as being “friends,” it’s clear that he actually wants to sleep with her. In fact, they establish that in the pilot. And it never changes.

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