I saw "Ask Harriet" during its brief run and I actually liked it, though I might've changed my mind if this sitcom had run a bit longer.
One thing that irritates me about most of these cross-dressing movies and sitcoms is that these guys never need to put any effort into acquiring female disguises: they just *happen* to have a handy supply of women's clothes, wigs, make-up and extra-large female shoes. In 'Some Like It Hot', the two male musicians leave the booking agency with no money and nowhere to live ... then they suddenly show up at the train station wearing complete women's outfits (which fit them!), plus luggage: how'd they get all that stuff, and where did they change clothes? At least in 'Mrs Doubtfire', Robin Williams needed some time to develop his female identity.
"Ask Harriet" was slightly atypical for a cross-dressed comedy, because male actor Anthony Tyler Quinn (what a bizarre name!) was actually somewhat passable as a faux female, although unusually tall and even taller in high-heeled boots. As "Harriet" in a long brunette wig, Quinn wore short skirts and knee-high boots that would've been quite sexy on a genuine woman. But where did tall Jack find pantyhose that fits him? I know petite women who can't find pantyhose that fits them.
There are some clichés here: macho sport columnist Jack Cody gets fired, but he becomes a better man by becoming a woman when he stops chasing skirts and starts wearing them to become agony-aunt advice columnist Harriet. Of course, the audience need to be assured that cross-dressing Jack isn't ... um, you know ... one of THOSE guys, so he continues to leer at the attractive women in the newsroom from behind his falsies, while they (the women, not the falsies) open up to 'Harriet' with some girl talk.
Most of the characters and dialogue were awful. In one episode, Ed Asner played a successful newspaperman who's also an idiot. Huh? Asner's usually convincing, but he wasn't believable here as an idiot.
The only person aware of Jack's double identity is his geeky little co-worker Ronnie, who clearly enjoyed controlling situations in which he's able to manipulate Jack into becoming Harriet. There was an annoying subplot (which never got very far) in which Ronnie and a very sexy woman (a real one) who works with him in the newsroom are attracted to each other but neither can work up the nerve to tell the other. Ronnie seemed to get more arousal from using Jack as his personal dress-up doll.
Female impersonation as comedy will usually get a quick laugh but is more difficult to sustain in a longer narrative. 'Some Like It Hot' worked because the cross-dressers were in a dangerous situation: they had to become live women to avoid becoming dead men. In 'Ask Harriet', Jack wasn't in danger of anything except losing his wig: I was never convinced that this elaborate sexual masquerade was the best career option for a male character who kept claiming to dislike dressing up as a woman. That was another cliché: we get the usual line about how it sure feels good to get back into men's clothes. Right, we get it, fella: you hate wearing women's clothes but you wear them anyway. Straighten your wig.
Rating: 4 out of 10. If you want to see a man dressed as a woman, either for comedy or for kink, there are better options elsewhere.
