Jenna Maroney from thirty rock
…Dateable that is, until she opens up an ancient sarcophagus, has her soul destroyed and her body possessed by a Cthulhu-esque demonic being. Then it would suck being her b.f.
Dateable men of the Whedon-verse:
Rupert Giles - Totally dateable. Stock up on the Taster’s Choice instant coffee now!
Xander Harris - Funny, cute in a nerdy way, but a lot of suppressed anger & self-esteem issues. Plus, he lives in his parents’ basement. Plus, he’ll string you along only to dump you at the most public, utterly humiliating moment possible. Undateable.
Angel - Cute, but dead. Moepy, whiney emo black hole of angst. And there’s that whole “moment of true happiness” curse - same caveat that applies to Fred applies to him. Undateable.
Oz - Dateable. Cute, smart, low drama factor. Just plan on doing most of the talking. And you know he’d never get too clingely or co-dependant because three nights of the month, you’re totally free to go out on the town without him. (And he owns lots of heavy-duty restraints, which might be fun…)
Riley - Handsome, corn-fed midwestern bore. Also incredibly insecure & needy - he’ll dump you on a whim, even when you’re in the middle of the greatest challenge of your life. Undateable.
Spike - Underneath all that smouldering, manly, virile, rebellious posturing, he’s really a big girly wuss who watches “Dawson’s Creek.” He’d also have no trouble replacing you with a robot double that caters to his every fetish. He’s also carrying a torch for his past loves. Also, he’s dead. Undateable.
Doyle - Totally undateable loser.
Wesley - Depends on which Wes, the Buffy-show pompous weeny prick (undateable) or the bad-ass Angel-show Wes (awesomely dateable.) Just remember to insist that he leaves you a bucket when you get into the whole S&M prisoner thing…
Lindsay - I’d say dateable, even if he’s essentially evil.
Gunn - hmmmmm, I’d say dateable. Decent guy, does the right thing. Drives a crummy truck, but nobdy’s perfect.
Lorne - His sense of humor, smart fashion sense, canny self-awareness & empathic abilities would make him a great b.f. - but, there’s that scaly reptile skin & horns…Ahhhh, what the hell, nobody’s perfect. Besides, the guy owns a BAR! How cool is that? Dateable.
Johnathan - Undateable.
Andrew - Same deal with Wes, undateable early on (weeny jerk, romantic obsessive, eaily manipulated), but showed evidence of growing up as he went along. If “Angel” had gone a few more years (and he got to make a few more guest star roles) I mightsay dateable.
I understand the prostitute=liar thing, but it’s more like “courtesan” equals liar. I mean, her whole living is convincing men she finds them attractive, sexy, and that they didn’t pay for her, not really, it just happened to be a financial transaction but she would have fucked them anyway.
That would bother me, too. How do I know she is ever telling the truth?
Princess Azula from the TV show Avatar: The Last Airbender is the epitomie of this. Hot, mad and bad.
They had a joke sequence in one of the episodes based on this exact theme - Azula tries to pick up a fellow at a party, only to scare him with her freaky craziness. 
Except for being hung up on another woman, who happens to live on his ship. I am the jealous type, and would never stand for that kind of arrangement. But the boy looks like he could be fun for a night… just ask Nandi.
Same goes for Simon. Cute. Great body. Fun for a night or two. But the boy is too much of a fop for me, and he has some SERIOUS baggage.
They might not be “outright nuts,” but they are definitely odd, and there are obvious problems with dating someone whose personal energy somehow attracts vampires, demons, etc., to the vicinity.
You beat me to it!!! I was totally going to say Zuko, from Avatar. Super hot. Lots of the right kind of angst to make a fun evening. But WAY too many issues.
You don’t, of course. So, it’s just like a marriage! 
Natasha Henstridge’s character from Species is just a bit too odd to date. (Not that I haven’t dated worse . . .)
How dare you blame Fred for that!
That was done to her by a combination of a deliberately-clueless ex-boyfriend and a deludedly-evil wannabe boyfriend.
The usual threats I not only have no intention of following through on but also am too lazy to actually type out.
I wonder: did he know that Lilah knew about what’s-her-name, the marginally-hot redhead, being in his closet? I mean, it’s not like she’d care even if he were abusing her, and she wanted to know where Angel was anyway and so wouldn’t interfere.
That bastard contributed to the murder of Fred. Such cannot be forgiven.
It’s not their personal energy; it’s living in Sunnydale. If you’re considering dating the ridiculously-hot Joyce, you probably also live in Sunnydale. Admittedly this shows bad judgment but, if you’re going to date a single mom thereabouts, it might as well be the Slayer’s mother.
Plus the MILF thing.
The Human Centipede.
Them Cartwright boys might have money, and two of them are fine looking, but I tells you, do not get involved with them. There be a curse what started with their father Ben Cartwright–any girl takes up with one of them ends up dying young.
Yep…there’s a reason all three of them have different mothers. (Poor pioneer Mrs. Kraus!)
Oh, you’re one of those people who doesn’t realize that Ben Cartwright was a serial killer. How sweet!
Oh, you’ve got the hots for Joyce Summers? Uh-huh. So, when are you going to rip off the latex mask to show us your true face?
Um…why would I do that? I mean, wouldn’t it be simpler just to murder the questioner?
Anyway, Joyce was comely. Not Natalie Portman hot, certainly, but at least, unlike her daughter, she did not have the body of a twelve-year-old boy. I mean that in the most insulting way possible.
Oh, yes. Completely batsh*t crazy, but hot (at least in my book).
Penny. She becomes a more interesting character later on, however.
I didn’t say I hated the character. I said I have a seething and sourceless hatred of what’s-her-name, the actress.