Portraiture

Wrinkles and All
Portrait photography, a specific category of commissioned work, by its very nature more likely gives an honest portrayal of how someone really looks than, let's say, a painting. The people in the portraits often like that ... and often do not.
One hears fairly frequently, for example, that "the photograph gave me wrinkles." Well, yes, some things seem to get minimized in photographs (e.g. dirt - one has to work hard to show dirt!), but others become emphasized, laugh-lines among them. Often we simply hadn't seen the wrinkles because we so dearly love the person we have known for decades that our brain still sees someone younger, or ...
... we never have our glasses on when performing ablutions in front of a mirror.
Cataract patients say the same thing to their ophthalmologist after lens-implant surgery, "You gave me wrinkles." But as with photographs, no, I'm terribly sorry to inform you, you had those wrinkles before. The lens - whether biologic or photographic - simply revealed them.

I don't have that many wrinkles - honestly! Nor am I that grey! (I am less in denial about the hair quantity ...) I was in fact also recovering from an abrasion on my forehead; I removed it in editing.
Hence: airbrushing. People touched up portraits years before digital photography, and in general terms: thank goodness! Who wants to remember, for example, every teenage blemish?
Hence, also: we have "portrait filters", added to the lens (more often in the pre-digital era), which confer an intentional softness to the image, over which I bet no one has ever argued.
Imagine this conversation with your photographer: "I don't look like that picture! I want a more honest portrait! I have more wrinkles! I earned those wrinkles, dag-nab-it, and I want them to show! Give me back my wrinkles!"
Ain't gonna' happen.
With digital photography, editing software offers a "smooth" button which just makes skin look better. With some of the portrait sessions I do, the skin looks harsh even to me, nothing like how it seemed on the person, at the shoot. So much for all of the hype about "high-definition" - now I've got to lower it.
Point That Camera Away from Me!
So, that's skin. But what if the subject simply doesn't like the way they look? Then you've got a bigger problem.
And people do say this to me, more often than you might imagine: "Point that camera away from me! I don't look good in photographs."
People who know me better have long ago relinquished - and I respect them in what I later show and in what I do not. They will be less accommodating in future otherwise!
Many of us do not like photographs of ourselves because, sometimes, our vanity simply interferes with our self-conception. I accept that as normal. But truthfully, the camera does seem kinder to some people than to others, and it doesn't always correlate with how gorgeous we actually look in real life.
Disliking one's own appearance too often impedes people from having a portrait done at all, a portrait which would otherwise so please their many family and friends for years to come.
Generally, a skilled portrait photographer can get something good from almost anybody. I'm not talking "cover-of-Vogue good", but not even the models look like that in real life anyway.
Getting something good might require a specific angle, a different light, and will almost always improve by backing away and using a longer lens - an issue quite frankly of the photographer using telephoto distance-compression to control ... nose-size.
Check out a further description of nose-size in photographs - and who wouldn't want to know more about nose-size?!? - here.
The Rapport Report
And no on can deny the importance, in portrait work, of rapport. The subject must feel at ease, happy (unless you want something else for a specific reason), and the expression must appear natural, which in addition to interpersonal skills, can require a finely-honed sense of timing.
The more skilled the portrait photographer, the more they can coax a good expression from their subjects, but it will require a flexible approach, tailored to each person or group individually, sometimes changing moment by moment. Never think that such things happen without effort.
Contemporaneously with the subject-photographer engagement, attention to all of the technical factors must continue, but in a way which does not impinge upon the client's participation. These factors include: light, the poses (what to do with hands!?), framing, exposure, focus, depth-of-field, background ... so yes, experience does matter.

That said, a little girl at a wedding picked up my camera and just snapped this of me. I think that the rapport carried it! (Her mother had a slight anxiety over the well-being of my camera - thank goodness for neck-straps!)
A friend has stated how much he enjoyed high-school yearbook photography, a genre many of us might consider quite routine. He knew that he had only a few minutes, and in that restrictive time-frame, he tried to get something "good" from each individual. I bet he felt tired at the end of the day, but he got asked back, year after year.
I list, as one of my several interests, "people who consider themselves unphotographable". Let me work with you - satisfaction guaranteed, or you can give me a nasty glare.
(And that might make an interesting photograph ...)

Winston Churchill by Ottawa's world-famous Yousuf Karsh - the photographer not seeking a "conventional" portrait, yet achieving something transcendent
Portraiture and Art
Let's combine the topics of "people" and "art". I captured this fellow at dusk one day in the Byward Market, a good decade ago, and have had it printed. It remains perennially popular with my growing fan-base (thanks so much to both of you). Either you like it or you don't, and if you like it enough, then you buy a print. Case closed.

Quite a random find, nowhere close to a formal portrait, but a portrait nonetheless
But if you sent me there to photograph you, then you might find that a different matter. You could have specific preferences, and they may only occur to you a day or two later, about the details of the framing, the light, the pose and expression, etc. From the stance of both the patron and the artist, the entire proposition differs considerably from buying "completed art".
Nothing has changed about the photographer's skill. Nothing might have changed about the patron's artistic tastes. Everything has changed about specific expectations - often unforeseen expectations - and it will always require some flexibility on the part of all parties concerned. A shoot will rarely go exactly as anyone foresaw it, and part of the adventure arises from the unanticipated. One only hopes that the results exceed expectations, but they will rarely exactly conform to expectations.
It could simplify to something as trivial as how to arrange a group of people - who should stand next to whom for personal reasons, vs. what makes an artistically more pleasing composition? Some groupings or poses just won't work. Some arrangements flatter the subject(s) more than others, and all remain honest. Sometimes one factor predominates, sometimes another. It involves more than pure "art". The client and the photographer will often have different views on which images they prefer. Fine. Just know that you will have to discuss it, and ultimately remember who pays the bill.
In a painting, you can alter reality more freely, and make people look better (or worse) - intentionally, we hope. In a photograph, post-processing (editing) notwithstanding, your options narrow somewhat.
Unposed Portraiture
-heartbreak ... and joy
What about the shoot when the patron says, "no posing, just catch us in action"? That could happen for example at musical performances. The photographer explains in advance about the limitations of that, and then self-amazes with how well it goes ... but we did not do a controlled, studio shoot, the lighting came from all over the place, everything pushing both the camera and the photographer well beyond their limits.
Frankly, the photographer may amaze him- or herself - but then add: "... under the circumstances ...". Hmm.
What happens then if the client feels less than thrilled with the photos? What happens if the photographer doesn't like the results enough to attach his name to them?
Many photographers won't do this kind of shoot at all, no matter how hungry, for those very reasons.
And yet in my own professional experience, often the client does feel thrilled, and I am amazed at how well it went; if one had said "no" to that shoot, then we would have eliminated the possibility - not by any means the certainty - of that satisfaction.

The incomparable Josée Brault, clearly unposed, in performance (Richard's Coffeehouse, Brockville), the camera the last thing on her mind - and yet I believe that we got something - maybe even something magical.
Unposed shoots always increase the unpredictability. Live with it ... or else don't do them.
So, portraits: these have provided a business base and a valuable service for photographers and clients respectively since the inception of photography, and indeed of other media, like painting and sculpture, long, long before that. The genre will not disappear anytime soon.
I cannot present as many examples as I would like because I ensure my portrait-clients strict privacy.
Good portraits, dare I say "great" portraits (and who would aim for anything less?), which transcend merely "in-focus, well-exposed, facing-in-the-right-direction likenesses", require a profound commitment from the photographer, but yes from the subjects also, on some level. We will never hear the final word on this category of photography, with the enticing and intriguing challenges both of creating art and of pleasing the client.