I haven't seen much of Sally Kohn but she seems like one of those irritating over-compensating for her own insecurity by being too dude-like lesbians. Hard to imagine hanging out with her.
Rachel Maddow, OTH, seems normal and secure to me. I've heard she's from the Bay Area, CA (like me) so maybe I'm just responding to the familiar way she speaks? I don't know.
What I do know is I would do Rachel if she looked as hot as she did in her yearbook pic: