River Tam was who I thought of first; I then decided that to be fair I should list off the other Whedon characters who qualified; the list grew till I decided that “every Joss Whedon character” would be simpler. (I’m happy to back that off to “most of Joss Whedon’s characters” though I think at least four of Skald’s “dateable” characters wouldn’t qualify in my book.)
what’s wrong with Robin 
Wait, what? I didn’t mention Peggy, or any of the other women (except Betty). I thought about saying that I would find most of the women on Mad Men quite datable, but this thread isn’t about who we would date.
ETA: It’s my impression that Peggy finds most of the men on Mad Men undatable, too, for the same reason I do. She may wish that Don had at least tried to hit on her, but in my mind, she’d have the good sense to take the ego bump and then turn him down.
Looking over your post I see you did write “most of the men on Mad Men.” I’ll call off the hamsters.
ETA: It’s not so much that Peggy wanted to sleep with Don, as it is that she’s vaguely insulted that he didn’t hit on her given his willingness to boff two secretaries this season. It was one thing when she thought he had principles.
And then she’ll either kill us all, or rub soup in her hair.
Would that be Tam Yum soup?
Quoted before by Lemur but deserves a second mention. How can you not want to date a girl who comes up with sentences like …
Wow, maybe I do need to watch Buffy, after all. I like frank honesty.
From Triangle:
Buffy: [Anya] dated a troll?
Willow: And we’re, what, surprised by this?
Willow: Distract him! Piss him off!
Anya: I don’t know how!
Willow: Anya, I have faith in you. There is no one you can’t piss off!
Anya: There are many humans who are stranger than me!
Willow: Uh huh. Well, unless I’m really wrong about Crazy Larry down at the bus stop, he’s probably not gonna turn Xander into a troll.
[URL=“Quotes - Triangle - BuffyGuide.com”]
I’ll take this one. Anyone who can have passionate, serious relationships with both Ted and Barney is not someone who is ready to have a long-term relationship.
And by long-term, I mean past a first date.
Jealousy, methinks. Willow never got over Xander entirely, “gay now” or no.
So then, not too odd to date? 
Quite so. I seem to recall him once saying that smart girls were hot, and her complaining – IN FRONT OF TARA – that she wished he’d have figured that out in 10th grade.
That brings up my problem with Kennedy as a love interest for Willow; Tara was good/interesting for Willow because Willow spent most of her life being the vulnerable one, who could be devastated by cruel or even thoughtless words - and never learned that she herself could hurt other people with thoughtless words or deeds. Tara gave Willow the chance to grow by learning that she needed to take effort to avoid hurting other peoples’ feelings (witness how the argument in with Tara “Tough Love” went) - whereas it’s hard for me to imagine Kennedy being hurt by anything Willow said.
(bolding mine)
I think you mean “never learned to care.” Willow knew she was being hurtful to Anya; she simply didn’t care, partly because she thought Anya’s past justified it and partly because, as Mr. Excellent observed, she was jealous of Anya and wanted to hurt her.
Willow was always a hottie, though she didn’t seem to realize it, and once she got some self-confidence she was quite charming. But she wasn’t nice – just good at counterfeiting it.
ETA: As for Kennedy as a love interest – my problem was simply that she wasn’t remotely likeable, whereas Tara was extremely likeable.
Well, I’m thinking about her treatment of Tara, where I think I can assume she did care, but didn’t realize how vulnerable Tara was (because Willow had always been the most vulnerable person in the room, until Tara came along). With Anya, yeah, she didn’t care, because of the reasons you and Mr. Excellent have described.
As I think on it, I think Willow is the prototype for the hot-but-undateable character, even more so than Greg House or River Tam. Unlike the latter she isn’t nuts, and unlikek the former she isn’t honest about her bad behavior or the reasons for it. Admittedly part of that is Whedon et al losing their nerve in the midst of the Dark Willow storyline–but as I’ve opined before, she was evil a long time before Tara died.
Absolutely - as far back as Oz and the werewolf girl or the delusting spell (I forget which was first), Willow showed a disturbing tendency to look for shortcuts in trying to solve her problems; tying that into a drug analogy was deeply disappointing.
The rumor is that Whedon didn’t lose his nerve, but that Ms. Hannigan was having a conniption fit about Willow’s dark turn. I think they spun it as a drug addiction to appease her.
There are a few wrestlers who come to mind here. Victoria (now Tara) is a prime example–the body of a goddess but a whole raft full of psycho. Daffney, same thing. Layla and Michelle McCool are arrogant little so-and-so’s who love themselves way too much. Lita would eventually cheat on you with your old friend, and Beth Phoenix would just end up killing you with snoo-snoo accidentally.
Of course, I’m just talking about their characters here. Lisa Marie Varon (who plays Victoria/Tara) is by all accounts a really cool, smart, friendly woman, and people seem to have nothing bad to say about Elizabeth Carolan (this one you can probably figure out).