Harry’s been a friend. You know he’s been a good friend of mine. But lately something’s changed, it’ ain’t hard to define. Harry’s got himself a girl and I wanna make her mine. It’s time for the latest installment in my series using only Spider-Man comics to examine the variety of romantic archetypes we find in literature (illustrating the variety of romantic experiences we find in life)! Here we see Peter in a good place. His best friend Harry Osborn is alive! Harry’s returned from an extended stay in Europe where he got sober. He’s in a new relationship with Lily Hollister, a girl he really likes. He’s starting his own business out from under the cruel shadow of his infamous father. He and Lily are trying to fix Peter up with her best friend, Carlie. There’s so much to celebrate!!! Oh, and Peter also kinda has a thing for Lily. He thinks she’s cute. In fact, he thinks she’s a “knockout.” In fact, he kinda struggles with not thinking about her. But it happens, right? While the significant other of a best friend should set our Bad Idea Sense tingling, sometimes we can’t help but be drawn to them anyway. Oh Peter, tread carefully here…
(And yes, I know my title references the Cars’ “She’s My Best Friend’s Girl” while the opening line is a modification of Rick Springfield’s “Jessie’s Girl” but I liked one for the title and one for the setup so I’m gonna need you to get all the way off my back about it because that’s how I wanted to do it. It’s two pop song references in one opening! You should be thanking me instead of judging me.)
At the heart of this age-old love triangle is the question – Why do we want what we can’t have?
However, before we explore this, we need to be clear about something at the start. People break-up. Sometimes people break-up with someone because they’ve met someone else. Breaking up isn’t, in and of itself, a bad thing. We break-up with someone because we’ve changed. All of life is about change! Biologically speaking, if we stop changing we die. The same is true in an emotional and spiritual sense as well. Sometimes we’re lucky enough to meet someone with whom we can change together, in compatible ways, for our entire lives. That’s beautiful! But when that doesn’t happen, the healthy thing to do is to break-up. Despite the messages culture indoctrinates us with, that’s beautiful, too. We should celebrate ourselves and those we love for having the self-awareness, the courage, and the self-love necessary to end a relationship when it’s no longer meeting their needs and making them happy.
But that healthy transition – breaking up when our needs are no longer met and finding someone who makes us happy and meets those needs – isn’t what this post is about. And it certainly isn’t what happens between Peter and Lily! No, this piece considers why we are sometimes drawn so magnetically to someone with whom we have no developed relationship, no natural chemistry, no obvious connection of any kind…you know, save their dating our best friend.

The aforementioned best friends enjoying an afternoon in Central Park. / Photo Credit – Marvel Comics
To make sure we’re all really soaking up the depth of the line Peter’s flirting with here, let’s frame Peter’s friendship with Harry. Harry’s father, Norman Osborn, is the Green Goblin. Yes, that Green Goblin. Harry’s father is Spider-Man’s greatest foe, the man who threw Gwen Stacy from the top of the Brooklyn Bridge, poisoned Mary Jane while she was pregnant resulting in her miscarrying their daughter, faked Aunt May’s death, and coerced Flash Thompson into heavily drinking after leaving an AA meeting only to then let him drive, resulting in a crash that left Flash with brain damage. Norman Osborn is a monster. Norman was a distant, emotionally abusive father to Harry, as well.
Despite his family history, Harry and Peter became best friends. Harry went to high school with Gwen and she and Harry both met Peter in college at Empire State University. Peter had no friends in high school (save the brilliant Betty Brant) but in college he finally began to develop a social circle outside supervillains. Harry was a core piece of Peter’s growing collection of natural supports. He dated Mary Jane for a time while Peter dated Gwen and the four of them enjoyed the few halcyon days their youths held together. Peter was there for Harry through his battle with addiction and as he tried to deal with his father’s cold disapproval. Harry looked to and cared for Peter and Aunt May as family, too. Harry would eventually marry Liz Allen, Peter’s old friend from high school, and they’d have two children together.
All wasn’t blissful as they grew up, though. Nothing stays peaceful in Peter’s world for long. Harry would learn of his father’s double identity when he found him dead in his Green Goblin costume. Blaming Spider-Man for his father’s death, Harry would assume the mantle of the Green Goblin himself and begin his own crusade against the wall-crawler. When he learns Spider-Man’s true identity, it drives a deep wedge into their friendship. Eventually, the descent into madness and addiction being the Green Goblin brought upon Harry would cost him his marriage and his life, dying in the Green Goblin costume like his father.

Mary Jane tries to talk Harry out of his final battle with Peter. / Photo Credit – Marvel Comics
Almost. This is comics we’re talking about after all. After Peter and Mary Jane sell their marriage to the Devil to save Aunt May’s life (because…comics), Mephisto takes everyone’s knowledge of Peter’s double identity as part of the deal. Not long after the start of this brand new day, Harry returns from Europe. He tells Peter while it looked like he was dead, the Goblin Serum he had in his bloodstream ultimately healed him (as it did his father (because…also comics)). Then, given a new lease on life, Harry disappeared to Europe to get clean. He went into recovery, leaving behind his use of alcohol, drugs, and the Goblin Serum. While in Europe, Harry meets Lily Hollister, a wealthy heiress herself. They begin a relationship which only grows stronger and more intimate the longer they’re together.
When Harry comes back from Europe in The Amazing Spider-Man #545, he introduces Lily to Peter and they try to fix him up with her best friend, Carlie Copper. While Peter doesn’t click with Carlie (yet), he and Harry do reconnect. They begin to hang out more and more. Harry’s there for the goofy best friend stuff – like being a brilliant wingman and trying to help Peter meet someone he does click with.

Photo Credit – Marvel Comics
Harry’s also there for the emotionally heavy best friend stuff, too. He and Peter can – and do – share the BIG things weighing on their hearts and souls.

Photo Credit – Marvel Comics
I love how Harry asks if Spider-Man is Peter’s boyfriend. I think this scene is so important in painting the full picture of their friendship. He jokes a bit, saying it would explain all Peter’s girl problems and why he’s always taking so many pictures of Spidey :). But it’s also a very tender and supportive moment. Harry is giving Peter permission to be open about his sexuality and his relationship with Spider-Man, if it’s a secret he’s been carrying and one he needs to share. In asking, he’s letting Peter know he’s comfortable with whoever Peter is and reassuring him there would be no judgment either way nor would anything change in their friendship.
When we look at Harry and Lily, we see they have a strong relationship, too. It would be easy to expect the children of two wealthy families (Lily’s father, Bill Hollister, is a D.A. who is running for mayor of New York City) to be self-absorbed party people, Harry and Lily connect in very beautiful ways. During a period in the comics where Peter’s love life is all over the board, Harry and Lily offer a strong example of a stable, supportive relationship.
When Norman Osborn – then director of the S.H.I.E.L.D.-replacing organization H.A.M.M.E.R. and leader of the Dark Avengers, after saving the Earth from the Skrulls’ Secret Invasion – visits Harry’s new business, the Coffee Bean, he couldn’t be more condescending. Lily is right there with Harry through Norman’s entire coldhearted visit and, once he leaves, Lily’s there to wrap Harry in love, support, and validation.

Photo Credit – Marvel Comics
When Lily’s father is seriously injured in an attack by Menace – the mysterious new Goblin terrorizing New York City – Harry’s by her side without question. In their sadness, in their fear, they find the strength to keep going in each other’s arms. They have become family to each other, bound in love.

Harry tells Lily he has no desire to be a part of his own family, but he wants very much to become a part of hers. / Photo Credit – Marvel Comics
Come The Amazing Spider-Man #586, Harry proposes to Lily. While they’ve only been going out for a few months, he loves her and he wants to officially make her a part of his family.
It’s all very beautiful. Buuuuuuuuuuuut, through all these relationship-deepening moments, Peter’s been having some more than platonic thoughts and feels about Lily. They just keep ramping up, too! In the beginning it’s a little awkward but mostly funny. It plays out in front of Harry and he’s obviously not threatened by it nor does Lily seem to see it as anything more than Peter just joking around. But as Peter spends more and more time with Lily, it becomes clear there’s more going on when he thinks of her than just joking around with his best friend’s girlfriend.
It begins at a fundraiser Lily is hosting for her father’s mayoral run. When she asks Peter for a donation, he’s worried she’ll think he’s “cheap…or not supportive” if he doesn’t make a real donation. It’s natural to want your best friend’s significant other to think highly of you but…is there more to why Peter’s concerned with Lily’s opinion of him? When he tells Lily he’ll pledge despite working for a paper that supports the other candidate, Peter says, “For you, Lily, I’m gonna live dangerously. ‘A.F.A.K.B.’ [Anything for a knockout babe]!”

Yes Peter, because OF COURSE you should be flirting with Lily as opposed to spending time with Carlie who is RIGHT THERE and SUCH AN AMAZING PERSON. Good call bud. / Photo Credit – Marvel Comics
Taking pictures of her for the celebrity section of The D.B.! (the tabloid The Daily Bugle became after Dexter Bennett bought it out from under J. Jonah Jameson while he was in the hospital after a heart attack) he thinks, “It’s impossible to take a bad picture of her. She’s gorg – GAH! What’s the matter with me? No way I can think about her that way while Harry’s seeing her. Forbidden fruit. Forbidden fruit. She’s ugly. Thing-ugly. Blech! How do I get myself into these things? Is everybody’s life as big a soap opera as mine?” No, of course Peter shouldn’t think about Lily like this while Harry’s seeing her. But what would happen if Harry wasn’t…?

Photo Credit – Marvel Comics
At the Rainbow Room in Rockefeller Plaza, Lily’s lips linger suggestively close to Peter’s as she asks him about the ethics of photojournalism. Peter’s not sure if there was, in fact, something suggestive there…or if he just wanted there to be. Was he imagining it? It was loud, was she just talking closely? And if there was something there, what’s he to do about it? He thinks, “Was it my imagination or was she…? And if she was, what do I do about it?” The existence of the question itself illustrates Peter’s growing conflict here.

Photo Credit – Marvel Comics
Despite being hounded by security for taking pictures he wasn’t allowed to take in a place he wasn’t allowed to be, Peter still takes time to drink Lily in when he runs into her on the dancefloor while trying dodge the security team.

He does this WHILE HE’S FLEEING FROM SECURITY. C’mon man! / Photo Credit – Marvel Comics
Then, while Harry’s on the phone with his monster of a father, Peter is trying to console Lily while her father’s still in the hospital. He takes her hands as they begin to talk…and then the intimacy of the moment escalates rather quickly. It’s clear Peter’s uncomfortable and, when Harry turns around, it’s also clear he gets the sense something more than copacetic was going on.

Photo Credit – Marvel Comics

What a tangled web you’re weaving my friend… / Photo Credit – Marvel Comics
While Peter asks, “Lily? What are you…?,” he was the one who first pulled her into the embrace they shared and he was the one who first took her hands. There’s nothing wrong with physical intimacy between friends. It’s another sad piece of societal indoctrination that presumes physicality of any kind, including holding each other, is only the prerogative of a romantic relationship. But we’ve already clearly seen Peter has more than platonic feelings for Lily. So this isn’t two friends holding each other through a difficult moment, taking strength and comfort in the physical embrace of someone you love and trust. This is an embrace that holds more and opens the door to the potential for even more.
Then in The Amazing Spider-Man #573, Lily kisses Peter! In the ruins of Norman’s office, while Harry’s looking all over for a file, Lily pulls Peter into a tight embrace and tells him, “You’re the good one. And throughout these last few days, with all the craziness going on… Seeing Harry’s father. Seeing what Harry’s like around his father. Well, sometimes I feel…like I chose the wrong guy.” This is no “friend kiss” they share!

Smooch Town: Population 2 / Photo Credit – Marvel Comics
Peter does pull away. He tells her, “Whoa. Stuff tingling. No. I mean – me. Friend. Harry’s. You. Girl. No.” It’s obvious, while he knows he shouldn’t do it, he’s turned on by it. Peter’s sexually attracted to Lily and the tingling he’s feeling certainly isn’t his spider-sense. And while Peter does pull out of the kiss, he never tells Harry about it nor does he talk with Lily about it either.
Is that Peter just avoiding the whole issue? Yes, probably. That’s a safe bet. Because having a conversation about kissing your best friend’s significant other with your best friend or with the significant other you kissed is uncomfortable. But I’d wager the root of his avoidance has a lot more to do with his own conflicting feelings here. Peter doesn’t want to hurt Harry. He doesn’t want to do what he “shouldn’t” do. He doesn’t want to do the “wrong” thing. And he “knows” any sort of feelings for or relationship with Lily is “wrong.” But none of that does anything to negate the fact that (and I adore how, after fourteen installments in this series, I finally get to use this phrase from Scrubs) Lily gives Peter “wowzers in his trousers.”[1]
When Ben Urich, Peter’s boss at the journalism-oriented paper Front Line which rose when The Daily Bugle became The D.B.! – assigned Peter a piece on Bill Hollister, he reminds Peter, “You told me that your relationship with Hollister’s daughter wouldn’t compromise your work on the election.” Peter couldn’t get more flustered any faster! He protests, “‘Relationship?’ We’re friends. Barely. Nothing compromising about friends.” Then he thinks to himself, “Except maybe the time she shoved her tongue down my throat. And I liked it. And she’s still Harry’s girl. Oh, boy.”

I wish we got to see Ben’s inner monologue as all this played across Peter’s face XD. / Photo Credit – Marvel Comics
Again we are left wondering why? Why is Peter so infatuated with Lily? We’ve not seen anything in Peter’s time with Lily to indicate a real romantic/intimate/personal connection forming. He mostly hangs out with her when they’re with Harry and the deepest conversations they’ve ever had are the ones above about her worrying for her father. Most of their interactions have been surficial. It’s not like Peter’s wanting for female attention or would-be romantic partners either! At this time in the comics, Peter’s had deeper conversations with Carlie – who is brilliant, compassionate, fun, well spoken, a great listener, and clearly interested in him, too. He’s also in the midst of a growing workplace flirtationship with Norah Winters, a reporter at Front Line. But despite these two intelligent, fun, attractive, available women who openly express interest in him, Peter’s drawn by a seemingly unstoppable force to Lily Hollister.
While being bitten by a radioactive spider and gaining the proportionate strength, speed, and agility of a spider is clearly fictional, our being drawn like this to the significant other of a friend isn’t. This happens! So why? Peter calls Lily “forbidden fruit” but that analogy implies a wrong choice we’re going to make anyway, just as Eve and Adam ate the fruit of the Tree of Knowledge in Eden despite God’s warnings. Are Peter’s attractions – and by extension, all those attractions we’ve had like this – grounded in envy? In jealousy? Is it that the seaweed is always greener in somebody else’s lake? I grant it is always better down where it’s wetter (take it from me) but is that the root of the whole thing? Do we just want what we don’t have for the sake of not having it? Or is doing something wrong just fun? And if so, why? Why do we like to do things we “shouldn’t”?
Their burgeoning connection isn’t exactly a secret either, as Peter learns when he’s on assignment with Norah at the Bronx Community Educational Outreach festival. But Norah isn’t the only one who sees sparks flying…as Peter learns when they run into Aunt May there and she adds her own two cents to the discussion. It is, without question, one of my favorite pages in any Spider-Man comic I’ve ever read XD.

Ahhhhhhhahahahahahaha, this is THE BEST. / Photo Credit – Marvel Comics
While Norah introduces herself to Aunt May as Peter’s alibi and Aunt May introduces herself to Norah as Peter’s conscience, it’s not like finding yourself infatuated with your best friend’s significant other always ends poorly. Look at George Harrison and Eric Clapton! George Harrison married Pattie Boyd (the woman for whom he’d write “Something”) in January of 1966. She would divorce Harrison for Eric Clapton (who would write “Layla” for her) in ’77 and marry him in March of 1979 (note, I’ve read several biographies on George Harrison – including his wonderful autobiography I, Me, Mine – and they’re all on my bookshelves downstairs but I’m too lazy to go get them so I’m just citing articles from the internet (but you should read books about and by George Harrison!)).[2] George Harrison and Eric Clapton met in December of 1964 and they became fast friends…a friendship that continued after Pattie left Harrison for Clapton! They remained best friends until the day Harrison died, with Harrison often calling Clapton his “husband-in-law.”[3]
But, to be fair, the Harrison/Clapton/Boyd example is less than helpful here. First, I’d wager the connections moving between all three of them are more akin to the natural changes mentioned above. There would have to be a lot of open trust, growth, and healthy communication for all that to work. Second, this is such a memorable example because it hardly ever happens! This is the exception to the rule.
Which is why being inexplicably attracted to our best friend’s significant other should set our Bad Idea Sense tingling…even though it doesn’t always work that way. For Peter, Harry, and Lily, things take a more traditional turn. It gets messy, real quick, as happens to most of us when we find ourselves so embroiled in a love triangle like this.
Remember Menace? The mysterious new Goblin terrorizing New York with a particular eye towards attacking the mayoral candidates? The Goblin who, on more than one occasion left Spider-Man seriously battered and broken?

Spidey doing…well, um, he’s doing about as well as he usually does against Menace :8. / Photo Credit – Marvel Comics
Yeah, well in The Amazing Spider-Man #585, Harry learns Lily is really Menace! She found one of Norman’s secret labs while dating Harry and figured adopting the persona of Menace could nudge the election towards her father – helping to a) scare away other candidates and b) illustrate her father is, in fact, tough on crime as Menace targeted him with extreme (if nonlethal) prejudice.

In the words of one of my summer campers from years ago who stumbled, care of uneven ground, and fell under the water when we had the kids at the beach, “I did not see dat comin’!” / Photo Credit – Marvel Comics
But, as was the case with Norman and Harry before her, taking the Goblin Serum affects her mind, turning her cold and monstrous. She reveals the truth of what happened between her and Peter – a kiss she gave him only to distract him from finding the entrance to Norman’s secret lab – in the cruelest way possible, savoring the hurt she can inflict on Harry.
Norman, of course, knew what Lily was doing. First he let her have her fun and then he began helping her. He tested a new form of the Goblin Serum on her, allowing her to physically transform into Menace instead of wearing a Goblin suit. He took her on as an apprentice, reveling in the terror Menace was causing to New York in general and to Spider-Man and Harry’s lives in particular.
Oh, and he had sex with her. Oh, and he got her pregnant. So now Lily – Harry’s girlfriend, the woman he loved enough to propose to, the woman who was beside him in the early stages of his recovery in Europe, the woman his best friend Peter has been lusting after, too – is carrying the child of his father Norman Osborn while she shifts back and forth between her own mind and the Goblin Serum-infused monstrous mind of Menace.
Ok, so maybe it’s not what happens to most of us when we find ourselves so embroiled in a love triangle like this. But it’s still a pretty good reminder that the exciting, naughty, alluring attraction we can feel to our best friend’s significant other, when it’s not grounded in organic growth and change alongside a real connection born from our needs being neglected by one person and met by another, is problematic. I still don’t know why we feel this energy. If you have any ideas, please let me know! But I do know the next time Peter sees a new girl with Harry and she’s watching him with those eyes and she’s lovin’ him with that body – he just knows it – and Harry’s holdin’ her in his arms late, late at night…maybe Peter should stop feelin’ dirty when they start talkin’ cute and instead turn his attention to one of the zillion other intelligent, competent, capable, funny, compassionate women who are inexplicably attracted to him despite his being a total flake. Otherwise he’s just going to keep getting punched in the head by the object of his infatuation while she’s carrying the demonic lovechild of his greatest enemy and no one wants that.

Photo Credit – Marvel Comics

There are plenty o’ fish in the sea and all that, Pete. You don’t need this. / Photo Credit – Marvel Comics
Want more of my li’l series exploring romantic archetypes using Spider-Man comics? Well you’re in luck! Check out:
Spider-Man and the Black Cat: Flirting with Perfection to see how the Black Cat represents those people we know may be wrong for us and/or we know it won’t work out with in the long run…but we’re drawn to them all the same and we seemingly can’t stop flirting with or the pursuing them no matter how hard we try :).
Spider-Man and Mary Jane: Soul Mates? (Y/N/Maybe) for an examination of Peter and Mary Jane’s relationship, with a focus on the question of Soul Mates as well as the classic romantic tropes of the will-they-won’t-they and best-friends-first relationships.
Spider-Man and the Spider Family: A Look At What Might Have Been… to contemplate the “What if…?” people we think of when we consider our romantic “what might have been”s care of the alternate reality series The Amazing Spider-Man: Renew Your Vows.
Spider-Man and Gwen Stacy: All the Beautiful Angst of First Love to consider how Gwen Stacy has far more significance than just “the girl who died” and how her relationship with Peter perfectly presents all the awkward, cringy, and still oh-so-magical moments of the first time we fall in love.
Spider-Man and Silk: You Gotta Love A Physical Attraction to look at Peter and Cindy Moon’s relationship as an example of those people who inexplicably turn us on. The attraction, the draw to these people, is like a force of nature, completely beyond our control. It’s fun buuuut complicated without romantic feelings, too.
Spider-Man and Captain Marvel: The Super Friend Zone which uses the one date Peter and Carol Danvers went on as the frame to examine the friends we’re attracted to, the nature of “the Friend Zone,” and what we do when we start to feel a li’l romantic and/or sexual chemistry percolating in a platonic pairing.
Spider-Man and Betty Brant: Complicated Affairs of the Heart uses one of the oldest characters in Spider-Man’s character history to explore everything from first crushes and first dates to the confusing pull of falling in love with someone who’s married.
Spider-Man and Michele Gonzales: Hook-Ups, Hang Ups, and Bad Habits and explore how all the personal problems and issues and baggage we have that we refuse to acknowledge/own/see can hurt our ability to make it work with a really fantastic partner, as well as what happens when we meet someone who calls us on all our shit.
Spider-Man and Mockingbird: The Allure of the Workplace Romance looks at Peter’s relationship with Bobbi Morse during his time as CEO of Parker Industries to consider why we are so drawn to the workplace romance…and what awkwardness may be waiting for us if it doesn’t work out.
Spider-Man and Jessica Jones: The High School Crush opens the door to reminisce about allllllllllll those awkward, anxiety-filled high school crushes we had and could never find the courage to act on while also inviting us to think about the influence we may have on all the people we hardly know who come in and out of our lives.
Spider-Man and Jean DeWolff: The Lonely Echo of Unrequited Love is a sort of mirror to the cute-anxious experience of the crushes we don’t voice in high school, as it examines the very real pain we can carry in our hearts when we love someone who has no idea how we feel nor loves us back in the way we love them.
Spider-Man and Debra Whitman: Substitute People and Surrogate Relationships explores the toxic relationships we find ourselves in when we don’t articulate our boundaries and advocate for our own needs within our relationships, why we may struggle to do so, and briefly considers the nature of abusive relationships as well.
Spider-Man and Danielle: Wait…Is This A Date? dives into those oh-so-awkward questions that haunt the beginning of any would be romantic relationship like Wait…is this a date? are Are we a couple now? and all the discomfort and relief trying to figure that out can bring.
Spider-Man and Anna Maria Marconi: The Healing Power of Love considers if/how we may be healed and thus saved by someone else in and through love their love. To this end, it examines a relationship “Peter” had with Anna Maria while Otto Octavius/Dr. Octopus was in control of his body and living life as the Superior Spider-Man.
Spider-Man and Cissy Ironwood: The “Hey, Whatever Happened To…?” Relationship uses the relationship created for Peter by legendary comic scribe Chris Claremont to consider those people we click with, go out with a few times, and then…they inexplicably disappear from our lives. There’s no fight. No break-up. They’re just there…and then they’re gone.
[1] Bill Lawrence, dir. “My Own Worst Enemy.” Scrubs, season 7, episode 1, NBC, 2007.
[2] History.com Editors, “Pattie Boyd and Eric Clapton are married.” HISTORY.com. Published November 13, 2009. Accessed October 3, 2021. https://www.history.com/this-day-in-history/pattie-boyd-and-eric-clapton-are-married
[3] Bikramjitmitra. “Exploring the unstoppable friendship of George Harrison and Eric Clapton.” Far Out Magazine. Published January 2021. Accessed October 3, 2021. https://faroutmagazine.co.uk/george-harrison-eric-clapton-friendship/