Every portrait photographer starting out gets told to buy the fastest lens they can afford and shoot wide open for that soft, blurred background, and I did exactly that for my first two years, until I actually looked critically at my own work and realized how often shooting wide open was hurting images rather than helping them.
The physics that actually matters here is simple: depth of field gets shallower as aperture opens, as focal length increases, and as your distance to the subject decreases. All three factors compound, which means the same f/1.4 aperture behaves completely differently depending on the other two variables, and treating aperture as the only lever you're pulling is where most beginners go wrong.
For a single, isolated subject with nothing else important in frame, wide open genuinely delivers what people want, I shoot single headshots at f/1.4 to f/1.8 regularly and the background dissolves into a soft wash that isolates the subject beautifully. But the moment a second person enters frame at a different distance from the camera, that same aperture becomes a liability rather than an asset. I learned this the hard way photographing a couple at f/1.4 on an 85mm lens, where the person standing six inches further from the camera than their partner came out visibly softer.
For couples and small groups, I've settled into f/2.8 to f/4 as my actual working range, not f/1.4, specifically to build in enough depth of field that both people land within the sharp zone even when they're not standing at exactly the same distance from the camera. This isn't a compromise I make reluctantly, the background is still attractively soft at these apertures on a longer lens, and I'd rather have both faces sharp with a slightly less blurred background than a stunning background with one face out of focus.
An 85mm lens at f/2.8 produces noticeably shallower depth of field than a 35mm lens at the same f/2.8, because depth of field compresses as focal length increases even at identical apertures and identical subject distances. This means I can shoot a group of four people at f/2.8 on a 35mm lens and keep everyone sharp front to back, while the same aperture on an 85mm lens at the same working distance would leave the back row visibly softer than the front.
Moving closer to a subject at a fixed aperture and focal length shrinks depth of field dramatically, a headshot at three feet has drastically less usable depth of field than the same lens and aperture at eight feet, which is why extreme close-up portraits often need to be stopped down further than a half-body shot at the same settings to keep the whole face acceptably sharp.
For group photos beyond four or five people, aperture alone often can't solve the depth problem, especially with multiple rows. I now physically arrange people to minimize the distance spread from camera to subject, angling the group slightly, staggering people diagonally rather than in flat rows, because no amount of stopping down compensates for a group where the back row is genuinely fifteen feet further from the camera than the front row.
The single biggest mental shift for me was learning to choose aperture based on how many people and how much distance variation exists in a specific frame, rather than defaulting to whatever aperture produces the prettiest background in isolation. A gorgeous blurred background behind a sharp single subject and a slightly less blurred background behind two sharp faces are both correct choices, they're just correct for different numbers of people in frame.