‘Dair’ was off to a good start, but no intellectual debates or drunken elevator lovemaking can make up for abusive dynamics and sloppy writing.

Few subjects will cause infighting among Gossip Girl fans like Blair Waldorf and Dan Humphrey’s infamous relationship in season five. Today, the community remains divided on whether the love affair was a stroke of genius or a ridiculous whim on the part of the screenwriters; predictably, defenders of the latter position resent the notion that Blair could give away her heart to anyone other than her One True Love, Charles Bartholomew Rapist Bass. Especially to a holier-than-thou gossip columnist like Dan Humphrey. How dare you, Josh Schwartz and Stephanie Savage?

Now, being a dedicated Gossip Girl… (‘hater’? ‘addict’? ‘essayist’?) … something, you bet your arse I’ve got some very strong opinions about that relationship. So here I am, never afraid to speak my mind and rail against the current, to set the record straight like a shining beacon of truth.

The Truth is that “Dair” was off to a good start. The screenwriters handled that relationship with great care and thought: it’s not the sort of immediate, abrupt falling-in-love that’s rampant on the show. On the contrary, their affair is introduced with much more subtlety, gradually evolving from mutual dislike to bonding over shared interests, to a tentative friendship and ultimately, love. It was far from the usual “I’m falling in love with you this Tuesday” that plagues Gossip Girl. I’ll give credit where it’s due.

Unfortunately, in spite of some genuinely touching moments, the whole ‘Dan falling in love with Blair’ thing still comes off as messy and unrealistic. Why?

  #1 Blair was abusive to Dan


No matter how much she claimed to enjoy their intellectual debates, the fact is Blair was incredibly nasty to Dan. From the very beginning, she was repulsed by his underprivileged roots (seriously, that was the only reason.) She never missed a chance to insult his background, his neighborhood, his education, even his work and aspirations as a writer. Everything about Dan war fair game and every inch of her oozed with loathing whenever she found herself in her presence. The only time she was genuinely nice to him was during their brief relationship, and even that never stopped her from taking a jab at Brooklyn.

Blair (comparing Dan to Serena’s stalker): Never-to-be-realized literary aspirations? Check. Townie? You’re from Brooklyn, so check. Giving up everything to be Serena van der Woodsen’s stalker? Check.


Dan: I haven’t given up anything to be with Serena.

Blair: Oh, of course not. Besides your time… and your dignity. You’re chauffeuring me around, aren’t you? Oh, and I’m curious, when was the last time you wrote anything? And scribbling D. loves S. all over your journal every night doesn’t count.

Season 4, Episode 11, “The Townie”

This delightful little exchange happens in season four when Dan and Blair team up to track down Serena’s stalker. For the record, this getaway is supposed to be their first time bonding, and they start going to films and art exhibits together afterward. Which, um, makes perfect sense. Of course Dan Humphrey would want to hang out with Blair Waldorf after hearing such sweet nothings! It’s no mystery that men love bitches, after all.

Seriously though, it’s unclear why Dan fell in love with Blair at all – never mind be her friend. Having mutual interests is one thing, but people usually need a little more than that to develop strong friendships. Surely Dan could have found someone else to dissect Rosemary’s baby with? I mean, he goes to college, he could join writers’ groups, for God’s sake. Why would he waste his time with a snotty socialite who’s never shown anything but contempt to him? Who insists that they sit far away from one another as they go to movies together because she’s ashamed of being seen in his company? And – most damning of all – why would he ever make her the muse of his debut novel? We’re talking about the woman who banished his little sister from New York and sabotaged her job interview with Tim Gunn, among many, many other things.

The most obvious explanation is bad writing. Unless…

#2 Dan was a doormat


… Dan has low self-esteem and will hang out with pretty much anybody. After all, he doesn’t seem to interact with anyone outside of the Upper East Side clique, and he does have something of an Inferiority Superiority complex as awkward, bullied outsider. Not to mention he’s been tossed around by Serena quite a few times during their relationship(s).

With Blair however, the doormatting reaches stratospheric levels. Not only does he fly to her rescue every time she beckons him, but he lets her boss him around, easily forgives her anything (even when she tries to steal his thunder at a writers’ event) and generally tolerates her bad manners without a hint of criticism. Her pointed insults at his style and background rarely elicit more than a chuckle, as if she were the cutest thing. The moments he calls her out on her antics are tragically few and far between. Instead, he waxes endless poetics about her perfect soul:

Dan: I have the feeling that the real Blair Waldorf is closer than you think. Wasn’t all that long ago that she and I were working side-by-side at ‘W,’ and I totally fell for her.

Blair: And what was that girl like?

Dan: That girl is fiercely strong, independent, outspoken, beautiful, capable of anything, and no man or magazine should be able to take that away from her.

Season 5, Episode 21, ‘Despicable B.’

… Yes, I guess that’s true, but you also forgot snobbish, self-centered, rude, classist, and mean. Also, when you were working side-by-side at W? You mean when she kept trying to sabotage you and get you fired? What the hell? Dan, seriously. You’re better than this. Go find some nice friends and a nice girlfriend. At least Serena never looked down on you for being poor.

#3 Blair ditched Dan for Chuck without a second thought

Blair: Dan is my best friend. When we’re together, it’s great. I feel strong and safe. Except in his neighborhood.

Eleanor: And with Chuck?

Blair: I’m vulnerable. He’s devastated me, but… he’s also made me happier than I’ve ever been. I-I just don’t know which kind of love is better.

Season 5, Episode 24, ‘The Return of the King’

To be fair, Blair falling in love with Dan never held much water either. Chuck Bass has always been her one and only: this has been repeated and demonstrated ad nauseam during the show. Aside from him, the only man she’d ever seriously considered as a life partner was a Monegasque prince. Sure, Dan’s sweet, but that’s not something Blair Waldorf values much in people. As such, her developing feelings for Dan in season five, a mere two episodes after declaring her undying love for Chuck, felt very sudden and out of the blue.

But her returning to Chuck after dating Dan for what, a week? was similarly abrupt. It took exactly one scheme for her to fall for him again, even though she’d said (two weeks ago) (or less? seriously the timeline in this show is fucked up) that while she “loved” him, she wasn’t in love “with him”, for her heart now “belonged” to Dan. So what gives?

On a side note, her choosing the kind of man who makes her feel “vulnerable” and “devastated” her, rather than the one who made her feel like an equal, is a pretty lousy message to send to a young and impressionable audience. Especially considering the way her dark beau angrily dismissed her once she opened up to him. Seriously, screenwriters. Shame on you.


#4 After their break-up, they went right back to casual enemies like nothing happened

For all the thoughtful build-up that led to the actual relationship, it’s shocking how poorly the break-up was handled. There wasn’t even a real break-up to speak of: Blair confessed her feelings to Chuck, Dan cheated on Blair with Serena, and they didn’t see each other the whole summer. When they meet again, they’re both set on new objectives and Blair is committed to Chuck. In the end, the entire Dair affair turned out to be a colossal waste of time.


What was the point of taking so much time to establish this relationship only to have it end like this? One week of dating and a quick, sloppy break-up? Awesome. What’s especially jarring is how little impact their relationship has on either of them. It’s rarely mentioned again and they finish the series in the exact same position as they’ve started: as casual enemies. See for yourself how Blair speaks of Dan during the finale:

Blair: Serena, we all hoped Humble Humphrey would overcome his Brooklyn roots to join higher social strata. It’s the American dream, but let’s face it, in his case, the dream has died. (…)

I know what I need to know, and that is Serena van der Woodsen will never end up with a powerless striver.

Season 6, Episode 10, ‘New York, I Love You, XOXO’

I’m sorry, is this season one all over again? Hearing this, you’d never think Blair’s heart once “belonged” to this man or that they’d shared a strong, intimate friendship. Sure, you could argue that she’s angry because of Dan’s hateful gossip columns, but seeing as she and her fiancé have done much, much worse to countless people over the years, that would ring a bit hollow. Her connection with Dan didn’t make her grow in any way: her disdain for the poor and the vulnerable remains very intact, along with her tendency to throw tantrums when things don’t work out her way.

As for Dan, true to Gossip Girl‘s flimsy characterization, he promptly forgets about Blair and declares his undying love for Serena (despite hating her two days ago) (despite trying to win back Blair’s affections two days ago also) (oh whatever season six i hate you.) To add insult to injury, he claims that he only pursued Blair because he was… afraid of his feelings for Serena? Ah, I love the smell of retconning in the morning.

Once again, this is an obvious case of bad writing. And yet… it’s not completely unrealistic. As I’ve noted before, Dan has a strong Superiority Inferiority complex. Maybe he’ll just fall in love with the most glamorous girl he can find: Blair had quite the allure as a future princess coveted by bad boy Chuck Bass, and Serena was definitely less cool at the time, as she was getting less attention and media coverage than her best friend. It’s entirely possible Dan’s got an artichoke heart and will dismiss previous liaisons in a heartbeat if it suits him, caring only that his belle be beautiful and desirable.

In any case, it shows how shallow Blair and Dan’s relationship truly was. He never cared for her all that much – and neither did she, since she went back to despising him and cooing in Chuck’s arms like nothing happened. That’s a shame. If Blair and Dan were going to end (or rather not end) things like this, the screenwriters would have been well-advised not to jump on that bandwagon at all.

I happened to watch Gossip Girl‘s finale before I watched seasons four and five. And let me tell you, I was shocked to learn afterward that Blair and Dan had been romantically involved. This was not apparent at all. And that’s the saddest part: the whole thing might as well have never happened.

the good gif