Privileged and miserably insecure Andy Bernard is The Office‘s cautionary tale about the limits of what wealth can (or rather can’t) do for you. Many Office fans found Andy’s arc disappointing, but his choices eventually proved how many who grow up in toxic, status-obsessed environments often don’t transcend their learned behaviors.

TRANSCRIPT

Andy: “Andy Bernard does not lose contests. He wins them. Or he quits them because they are unfair.”

Privileged and miserably insecure Andy Bernard is The Office’s cautionary tale about the limits of what wealth can—or rather CAN’T—do for you. Amazingly, over the seasons, he developed from an irritating, outburst-prone bro-y brat into a nice guy we could root for, even if his nonstop singing and excess of privilege remained a little annoying. Then, it all changed; in the space of a season, Andy’s character quickly spiraled back to his starting position of spoiled, selfish, and totally unrelatable.

Many Office fans found Andy’s arc disappointing, but look a little closer, and you’ll see that it makes perfect sense for Andy’s character to regress in Season 9. He’s the embodiment of the phrase ‘money can’t buy you happiness’—wealthy and privileged but always empty, as evidenced in his impulsive decisions, anger outbursts and relationships that never last because he hasn’t learned how to value the qualities that are actually important in other people. While we (and perhaps Andy himself) were encouraged to hope that he really could be a deeper or better person, his choices eventually proved he wasn’t—just as so many people who grow up in toxic, status- and wealth-obsessed environments don’t transcend their learned behaviors.

Here’s our take on what money couldn’t buy Andy Bernard.

Walter Sr: “How long are you gonna go on needing my approval?”

Darryl: “I think if I had parents like that, I’d be trying to convince everyone all the time how great I was, too.”

Andy’s Very Unhappy Childhood

Andy grew up enjoying the considerable wealth and privilege of someone in the upper echelons of the WASP elite. His family owned a boat, he has a trust fund, and in a deleted scene we hear that his family was even wealthy enough to donate a building to get him into Cornell.

Andy: “A lot of people were like, ‘Oh, you just got into Cornell ‘cause your dad donated a building.’ I got into Cornell ‘cause I’m smart enough to have a dad who donates buildings to things.”

It’s revealed that Andy’s family money comes from slave transportation, a fact that Andy is shielded from until adulthood. He’s clearly been so ensconced in his privilege that he’s never stopped to question its source.

This unquestioning aspect of his nature extends to other aspects of his life. In particular, Andy’s firsthand accounts of his childhood are disturbing, but he presents them as though they’re normal. Actually, his parents evidence aspects of narcissism and in turn, Andy meets several criteria of a narcissist’s child, as outlined by Forbes.
Andy: “I was named Walter Jr. after my father until I was about six or so. My brother was born, and my parents felt he better exemplified the Walter Jr. name, so they gave it to him.”

• “[He] never feels good or valuable enough.” One distinctive trait of narcissistic parents is the way they play favorites, pitting their children against one another.

Andy’s parents making him feel Walter Jr. is superior to him continues into the kids’ adulthood.

Andy: “​​They gave me this old family ring to use on her… Mom took the main diamond out, she thought that had more of a my little brother kind of vibe to it.”

As a result, Andy is:
Andy: “I just thought if I could throw this great garden party and show you how respected I am that you’d be proud of me.”

• “deeply insecure, and overly-worried about what others think of him”, especially his family.

He craves connection with other people and becomes almost aggressively people-pleasing, trying to force bonds that on some level he believes just won’t happen naturally. Calling Jim ‘Tuna’ for example, after the sandwich he eats on his first day in the Stamford office, is Andy’s attempt to ingratiate himself with the new, cool guy, as is the screensaver he adopts to impress Angela on day one in Scranton. Andy’s intense people-pleasing also leads to him withholding truths—like not telling Erin about his previous relationship with Angela even though they work in the same office, and this just leads to humiliation for both of them.
Andy: “I have made non refundable deposits at four totally different wedding locales.”

• “[Andy] can be afraid to speak up confidently or challenge others” Andy regularly gets himself into situations where he knows he’s unhappy, and he allows other people to steamroll him. This is evident in the nature of his relationship with Angela—he goes to incredible lengths to try to please her, while receiving no affection in return.

Angela: “Dangerous, tacky, sharks, haunted. No.”

He pursues Angela, partly because he wants to legitimize his position in the office by dating a colleague, but also because she embodies a lot of the attributes he’s been conditioned to want in a partner, like being withholding and disapproving. Despite Angela seeming to recoil from physical contact with Andy (while cheating on him with Dwight) Andy pushes forward in his one-sided relationship with her—even getting engaged without noticing (as everyone else seems to) that she clearly doesn’t like him. Meanwhile, he’s so afraid of rejection he avoids telling Erin he likes her, instead going to elaborate and expensive lengths to indirectly express his feelings without making himself vulnerable.
Another characteristic Andy shares with other narcissists’ children is that:
Andy: “Scranton branch is closing? In your face!”

• Even though on the surface, he’s always putting being liked and avoiding conflict first, Andy suffers from regular angry outbursts. It’s likely that because his family is so toxic, he’s never learned to regulate his emotions. Instead, after constantly trying to smooth situations and appease others, his genuine emotions bubble to the surface in the shape of unbridled fury. This characteristic is a window into the sheer entitlement that resides in Andy.

• He’s really competitive. As a kid, Andy had to fight hard for affection and recognition, so as an adult, he’s always seeking ways to one-up his colleagues, even when there’s no room for a winner.

Jim: “Well, I work here now.”

Andy: “Mmmm.. suck-ah!”
Also characteristically for a child of narcissists:
Andy: “Sorry I annoyed you with my friendship.”

• “He sometimes feels used by work, and can’t understand why his career feels difficult.”

• “Andy forms relationships, both at work and in his personal life, that are deeply challenging and unsatisfying”.

Because he wasn’t given the opportunity to develop strong bonds as a child, Andy thinks that relationships should be materially beneficial in some way. He is constantly pouring energy into relationships with people he thinks can advance him, but because he doesn’t know how to read people, these interactions can be really awkward.

Andy: “Wings. Shots. Drunk. Waitresses, hot. Football… Then a quick nap at my place and we’ll hit the tiz-own.”

Michael: “No. I don’t want to do any of that.”

He hasn’t learned how to form genuine attachments; rather, he has a formula that he sticks to when trying to bond, and his resulting relationships are surface deep.

Andy: “Name repetition, personality mirroring, and positive reinforcement through nods and smiles.”

He loves the idea of being part of something, which is why he’s even happy to be given vaguely offensive nicknames.

Before we know how complicated Andy’s childhood has been, these factors all add up to make him seem unlikeable when he first joins the show. He’s actually vulnerable, but he masks it with aggression, and he uses his wealth and social status to cover up his anxieties. He turns his Ivy League education and preppy upbringing into a shorthand to claim superiority over others—appearing like a walking cliché of the entitled Ivy League bro.

However, the beginning of his redemption trajectory starts with the anger management classes he is mandated to take by corporate. And eventually his time in the office becomes a form of therapy, gradually transforming this sole lasting Stamford transfer into a relatable human being.

The Office as Andy’s Therapy

Michael Scott regularly talks about the office as a family, but actually, this idea is put into practice for Andy more than anyone else. As much as he brags about his university experience, because he thinks it gives him value,

Andy: “I was a freaking rock star in college. When I joined Here Comes Treble, that’s when I became somebody.”

it’s eventually shown that even Andy’s a capella ‘friends’ from Cornell are more antagonistic competitors to him than pals. And if we break down his descriptions of his time there, a lonely picture emerges.

Andy: “Kids would gossip about me… They would say things like ‘Oh, this guy’s going to fail this class.’”

Being at Dunder Mifflin Scranton is the first time that a group of people have welcomed Andy and cared for him relatively unconditionally. They’re not interested in his achievements or snob credentials, but they do accept that the bragging is part of him, and treat him like a brother who’s just sometimes a bit annoying.

Andy ends up rewarded with friendships and the trust of others. He strikes up an unlikely relationship with Darryl, and they form a band with Kevin. Pam starts looking out for him, too.

Pam: “It was fun, though, because I got to spend the day with Andy Bernard. He’s really cool.”

And as these people begin to see the good side of Andy, he symbiotically seems to become a better person. One example of this is when the whistle blows on Sabre, which is a huge departure from his upbringing.

Andy: “The Bernards, for generations, have silenced whistleblowers. It’s how we made all our money.”

As a result of these improvements in his behaviour, he gets better things, too. The combination of gradual improvement and more genuine relationships turned him into a character we could relate to. He wasn’t perfect, but he was getting better, and what’s more, we could almost feel that he really wanted to be nice.

But, for a person who has experienced the levels of emotional neglect and manipulation that Andy has, smooth sailing into better relationships with others and oneself is unrealistic…

Andy’s Decline (and Why It Makes Sense)

Even though he does improve throughout Seasons 3-8, we’re given suggestions that Andy is at risk of returning to his original character. He remains obsessed with Cornell, he continues to live in the past, and he’s still desperate for his dad’s approval.

Darryl: “You did good. Real good.”

Andy: “Thanks, Dad—Darryl.”

He has a diminished sense of self; he’s not really sure who he is, which is why he puts so much value in identity markers.

Andy: “If I am not Boner Champ, I don’t know who I am.”

And as a result of his difficult childhood, Andy self-sabotages. He seeks relationships with the wrong people. When he does start dating stable, genuine Jessica, he sabotages that. And while we may at that point be rooting for him because we’ve invested in his feelings for Erin, he likewise ends up trashing his relationship with Erin, too. Even though Andy has waited so long and worked so hard for Erin, he can’t understand her, partly because they come from such different backgrounds (Erin growing up not only poor, but in the foster care system).

He’s been shaped by his parents’ values, and those are difficult to shake: he prioritises status and wealth over genuine connection and hard work. When he finds out his parents are bankrupt, briefly “better Andy” takes control, making responsible choices to take care of his family.

But then—upon seeing his dad’s boat again, which he needs to sell—makes the impulsive decision to abandon his job and his girlfriend just to sail to the Caribbean and relive the glory days of being someone who owns a boat. The boat trip is the point at which Andy’s arc goes into sharp decline. It’s as if as soon as he steps away from Dunder Mifflin, where he is cared for, and back into the realm of his toxic family, symbolized by the boat, he quickly unlearns the years of improvement he’s made, regressing into the patterns of his economically rich but emotionally impoverished childhood. He remains preoccupied with things that don’t really matter, continuing to invest more into the past than his present with a girl who loves him.

Erin: “The more I hear about all this a capella drama, the more I think it’s kind of pathetic. But, when you’re with someone, you put up with the stuff that makes you lose respect for them, and that is love.”

These words of Erin’s are so revealing because they underline how Andy’s learned behavior leads to someone who doesn’t invite our respect—because he doesn’t respect what’s truly valuable in others, like patient, caring, kind, down-to-earth and fun Erin.

We also see evidence that, although Andy has benefited from the friendships he’s formed in the office, he hasn’t put in any work on top of that to address his privilege.

Andy: “I’m not gonna apologize for my family’s wealth. That wealth could one day benefit society… if capital gains are ever taxed at the same rate as earned income.”

His failure to reflect honestly on the wider implications of his wealth and place in the world makes it easy for him to regress; as with a lot of Andy’s enterprises, his self improvement was surface deep, and ultimately self-serving.

Conclusion

Because he craves immediate success without much investment, Andy leaves the office to seek fame and fortune as an actor or singer. He chooses the reality TV-talent show route, which is symbolic of this quick fix formula.

Andy’s unrealistic expectation of sudden stardom and inability to logically plan for the future are symptomatic of his privilege, too. He’s always had money, and that’s fooled him into thinking getting results is always as simple as making the choice to write a check.

Erin: “You could just—”

Andy: “Make a donation.”

Erin: “Well, I was gonna say be a mentor.”

Andy: “Yes. I am gonna make a donation.”

It’s not required him to learn to understand how he’s truly perceived (which is… as someone who’s not actually that good at acting or singing.)

Dwight: “I have known you for years, I have seen you perform—dear god, don’t quit your day job.”

His entitlement and delusion lead to a moment of such grandiose humiliation that it’s a viral sensation.

But then, Andy gets a “happy ending” of sorts—at least from his point of view. In the show’s final episode, Andy’s back at Cornell, working as an admissions officer—a job he ironically played around with back when Dwight wanted to apply to Cornell. In other words, it’s as if Andy is living in a metaphor for his regression—now literally getting to evaluate other Ivy League hopefuls and decide if they get to share in his status and privilege.

Yet despite all his posturing that he wished he could go back to Cornell, now that he’s back there, he’s longing for his time at Dunder Mifflin.

Andy: “I got my dream job at Cornell and I’m still just thinking about my old pals. Only now they’re the ones I made here.”

On one level his words are just a general warning about the pitfalls of a nostalgic outlook. But we can also read this as proving he’s finally realized what he needed to, all along, but just a little too late—that fortune and elite pedigrees can’t buy you happiness, and nothing compares to living in the moment with people you actually like.

Andy: “I wish there was a way to know you’re in the good old days before you’ve actually left them.”