TV Boyfriend Bracket Voting Round One: It’s Complicated

Well, readers, the moment is here. The voting is officially open, and I need your help in crowning the ultimate TV boyfriend. Here are the rules:

  1. Don’t bitch at me for who’s in the bracket and where they are seeded and who was left out. It was a very scientific process involving several bottles of wine.
  2. I get one veto in the first round – after that, it’s completely up to you. This is really to make sure The Piemaker isn’t voted out because not all of you were smart or cool enough to watch Pushing Daisies. I reserve the right to wait until all four brackets are voted on before I determine how to use my veto, unless something so egregious occurs that I must fix immediately (ahem, the Piemaker, ahem).
  3. We’re grading on boyfriend qualities here, ladies, not who you want to sleep with. Yes, Jon Hamm is an incredibly handsome man. We’re not voting on Jon Hamm’s physical attributes. We’re voting on Don Draper’s relationship potential.
  4. That’s not to say there is any kind of specific criteria that we’re grading on across the board. I’m well aware that 99% of HIMYM viewers think Ted Mosby is a douche. Well you know what? I’ve been told I’m attracted to douches, so I’m ok with dating one if he’s cute and funny and smart and loyal. If you are ok with being cheated on, or dating a guy with a drug problem/short temper/criminal record, by all means, go for it.
  5. Campaigning is allowed. You are encouraged to plead your case in the comments section or email the link to the friends you analyzed Dawson’s Creek with in high school or tweet at Jason Segal to try to gain his support. In fact, definitely do that.
  6. Each round will be open for two days of voting.
  7. Have fun.

If you need to be refreshed, you can find the entire bracket here. We begin tonight with the It’s Complicated bracket – the bracket that could very easily have been called the Hot Asshole bracket. These are the guys you know you shouldn’t love, but you can’t resist. It’s definitely the sexiest bracket, but also the most unreliable. You know they’re trouble… Read on and vote at your own risk.

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(1) Big – Sex and the City
Mr. Big (aka John James Preston) is the classic New York power player: suits, cigars, steak dinners. Hell, he’s the Chrysler Building. He is one of very few men who can pull off winking and calling his girlfriend “kid” as being charming, not creepy. Sure, he has some commitment issues (and two ex-wives), but who else will show up outside your apartment with red balloons and champagne for your birthday? It may take him awhile to get there, but a man like this is worth the wait. P.S. He is really very funny and owns half a vineyard.


(16) Gregory House – House
Pros: Brilliant doctor, magnetic personality, caustic humor, piercing blue eyes. Cons: He hates everyone and everything (except his precious Vicodin) and may drive his car through your living room on purpose, out of spite.

(2) Tim Riggins – Friday Night Lights
Smoldering doesn’t even begin to describe how hot this football star is (we don’t call Kris Letang the Tim Riggins of the NHL for nothing), but underneath the sexiness and the hair, there’s a really good guy inside. He’ll take the rap and go to jail in his brother’s place, so his brother can stay home with his newborn child. Sure, he dropped out of college, but he’s so much happier working on cars and drinking beers in the open Texas air… and a guy who follows his heart like that is hard to find. Especially one with bedroom eyes and a slow, sexy drawl. Texas forever, baby, and I don’t even like the south.


(15) Michael Vaughn – Alias
Michael Vaughn is one of the good guys, but he’s a secret agent, so that certainly complicates things a little bit. He speaks French, he was completely devoted to partner and eventual love interest, Sydney, and… who are we kidding. He’s going up against Tim Riggins. Even a sexy CIA agent can’t compete with that.

(3) Dylan McKay – Beverly Hills, 90210
The brooding bad boy that set the brooding bad boy standard. Dylan lived by himself, drove a Porsche, and seduced Midwestern good girl Brenda Walsh within about five milliseconds of enrolling at West Beverly High… then slept with her best friend Kelly while she was in Paris. And while we don’t condone cheating here at HIMTM, you also have to admit that this one time was maybe forgivable, because after countless years, significant others, drug problems, a wife being blown to smithereens, a disfiguring house fire, and Valerie Malone, those two crazy kids ended up together after all.


(14) Fox Mulder – The X-Files
With Fox Mulder, you have to know what you’re in for: severe paranoia, complete distrust of the government, a sister who was abducted by aliens, countless shady figures who want him dead, a slight interest in pornography, and a tendency to wake you up in the middle of the night to follow a lead. But you also get someone who is smart, loyal, protective, and wickedly funny, who was educated at Oxford, became one of the most brilliant profilers the FBI has ever known, who is passionate about his work and the quest to find the truth, and who looks damn good in a leather jacket.

(4) James “Sawyer” Ford – Lost
If you only watched the first few seasons of Lost, you’d still think Sawyer is the cocky, hot-headed con man that Kate was drawn to precisely because she knew she shouldn’t be. But then something happened: Sawyer jumped out of a helicopter so his friends could make it off the island alive. He grew up, and somewhere in the 1970s, he emerged as a trustworthy figure within his workplace. (He couldn’t help that his workplace happened to be the shady Dharma Initiative. He was stuck in another decade!) But most importantly, he became a loving and devoted boyfriend to Juliet. Underneath the rugged exterior, there was a really wonderful guy. It just took the right woman to bring it out.


(13) Will Gardner – The Good Wife
You know you shouldn’t, you try to resist, but you can’t help yourself…Will Gardner is one of *those* guys. A total charmer, kind of a player, definitely a little shady (hello, gambling addiction!). Super successful and smart – he started a law firm with Christine Baranski, so you know he has good taste in women – and loyal to old friends. He gave college crush/good wife Alicia Florrick a job when she desperately needed one. And then he seduced her.

(5) Mark Sloan – Grey’s Anatomy
They don’t call him McSteamy for nothing. This man is confident and sexy and oh so smooth. He is a renowned plastic surgeon who stitches up his own face (hot) after a fistfight (also hot) because no one else can do it as well. Yes, he slept with his best friend’s wife, but only because he really loved her and his best friend is kind of a wienie anyway. In his middle age he has blossomed into a great friend, fuck buddy and father. And he’s still steamy as ever.


(12) Chuck Bass – Gossip Girl
Chuck Bass is about as damaged as they come. He’s got more intimacy issues that I could possibly describe here, but he’s also devastatingly handsome, filthy rich, and incredibly loyal to his friends. He may take awhile to say “I love you,” but when he does, he does it with style. He may then also sell you to his uncle to save his hotel, but… macaroons!

(6) Alex Karev – Grey’s Anatomy
Okay, he is a total jackass, but he’s a lovable one. Karev might be considered a “strong, silent” type except that he constantly runs his mouth in the most inadvisable way possible. But he keeps his painful childhood to himself and never uses it as an excuse for the mistakes he makes now. He is blunt and sarcastic and brave and honest. He gives fantastic supply-closet-sex hair. He married the love of his life when she was dying from a brain tumor and turned out to be a damn good husband…at least he was, until she ran off and left him heartbroken. You’d probably be a jackass too.


(11) Barney Stinson – How I Met Your Mother
Let’s be upfront with this: there is a high likelihood you will contract an STD by sleeping with Barney. He’s the kind of guy who keeps a scrapbook of all the women he’s slept with. He used to think his dad was Bob Barker. He’s a little too fond of catchphrases. But Barney isn’t without his merits: he knows the value of a good suit, he’s absurdly rich even though we have no idea what he does, he makes a great get psyched mix for New Year’s Eve, and he can appreciate a brunette hockey fan who likes to hang with the boys. That gets points around here. And occasionally his ideas, however misguided they are, make sense – the Lemon Law should totally be a thing.

(7) Pacey Witter – Dawson’s Creek
Sure, he started off by losing his virginity to his teacher. And yes, he has some deep issues which stem from his alcoholic, abusive father. And really, you should never break the bro code and go for your best friend’s girl. But who could resist him? He’s cute, funny, spontaneous, driven by passion, and has quite a way with words. You know you’re going to end up with him eventually, so why resist?


(10) Schmidt – New Girl
Let’s see… he cooks, he cleans, he is happiest in a new pair of perfectly creased pants designed by a man named Calvin, and all he really wants is to see his roommate’s penis. Schmidt may come off as the douchebag (as evidenced by the ever-growing fund in the douchebag jar) and he may be like Ellis Island (he accepts everyone into bed), but he’s lovable, funny, and he has to be doing something right, because Cece keeps coming back for more. He is a sexual snowflake, after all.

(8) Doug Ross – ER
A dashingly handsome doctor with a bit of a troubled past, Doug Ross is the kind of man you just can’t help wanting. He is a pediatric emergency medicine physician and of course, watching this extremely charming man help sick kids only adds to his charm and will make your ovaries burst. He once saved the life of an injured boy trapped in a storm drain. Again, there go my ovaries. So he’s a bit of a womanizer, but it’s hard to blame him due to his childhood with an abusive father. And when his lifestyle of perpetual one-night stands goes too far, he changes his ways and and commits himself to winning back the heart of the woman he really loves. Don’t you kind of wish that woman was you?


(9) Don Draper – Mad Men
War vet who stole someone’s identity. Has a drinking problem. Has a womanizing problem. Brilliant at his job. Looks absolutely lickable in a suit.

Those are your options, ladies. Choose wisely.

49 thoughts on “TV Boyfriend Bracket Voting Round One: It’s Complicated

      • You actually have a better chance of having sex with Don Draper if you are not in a relationship with him…

      • Emily is right. This is the boyfriend bracket, not the one night stand bracket. I worry that if Don Draper makes it to the second round of this thing, we’ve set back the feminism movement at least 50 years.

    • Yeah, hello, it’s not like voting out Don Draper leaves you without a hottie to sleep with. Hello – do you remember Doug Ross?

      • Really! And Doug Ross has the sexiest crinkly-eye smile. Don Draper just smokes cigarettes and glares at people.

  1. This is so high-tech! I love that I immediately get to see the results! And thanks for the bios! There were a few guys I didn’t know and I based my vote totally by your descriptions!

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  3. Well done Brenna! I hope your blog starts to get some attention beyond the “regular crowd” I think people would love to read your musings 🙂

    • I was never much of a Sawyer fan while Lost was on the air (Sayid & Desmond were my guys, as you’ll see later in the brackets), but writing about him & recalling how amazing he got near the end made me love him even more. I’d get lost on a deserted island with him any day!

  4. Tim Riggins better win. And as for Don Draper? I voted for him. I know he’s a mess. I know I would never want to seriously date him? But for a first round pick, he’s mine. Doug Ross was hot. True. But he was also a bit of a modern day Don Draper. He slept around, he was emotionally gaurded. And Don wears a suit, not scrubs. I realize I’m part of the problem.

    But I did put my final four in a blog post today.

  5. This bracket is the BEST IDEA EVER. My colleagues do brackets for random things at work and now I want to do an official online one. Love it! Whatever amount of time you put into this is so worth it in my book.

    Now, can we please talk about CHUCK BASS? How is he not winning? Maybe I’m the only 26 going on 14-year-old that is reading your blog but Chuck is one hot, angry orphan. And I love him.

  6. Ok, seriously…It’s sort of freaking me out that Dylan McKay is beating Spooky Mulder. Come on, people. I don’t have IU anymore. Give me this.

    I Want To Believe.

  7. SO MUCH FUN Brenna! And I agree with Beth – thanks for the bios! I’ve never watched Lost or The Good Wife so those were really helpful! I did go for Tim Riggins (although I do love a guy who can speak French), and Doug Ross came in ahead of Don Draper for me – when it came down to it I decided I’d be much happier living with Doug for the rest of my life than Don.

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