No Stupid Questions

There's a problem in answering this. We don't know what the actual cause is, and we don't know if it's acne, a reaction to products, ingrown hairs, or just irritated skin that mimics one or multiple of those. So, be aware that you're going to see responses that may not address the real problem but is still good in general, even if it doesn't lead to a fix.

So, I used to be a nurse's assistant. Shaving people is part of that job sometimes. Back in the day, one of my teachers was even the crazy type that pulls the whole "shave a balloon" thing. Which, while entertaining and slightly useful, doesn't actually teach what it takes to shave a person.

Anyway, shaving is always a skin irritant. It's a matter of degrees. Most of the time, if you follow the core principles, that irritation is going to be below the threshold where it's noticeable for more than a few minutes at most.

Number one rule is that sharp razors cause the least irritation, and are less likely to result in nicks. Doesn't matter what kind of razor you use, it has a limited range of uses before it needs sharpening or replacement. A straight razor, you strop every time you use it. Safety razors and most of the disposable head razors (no matter how many blades) expect to get three shaves at most before you start feeling the difference.

Yeah, that's less than what most guides will say. That's because you can definitely get more shaves in before it turns into a problem. But you'll feel a change before it gets to the point where you're losing the ability to slice smoothly and it turns into damaged skin. Most safety razors, assuming your facial hair isn't absurdly thick and dense, expect to change the razor after five or six uses. Some of the multiblade heads can stretch a little more up to maybe ten shaves total, but I'll be damned if I'm going to shave myself or anyone else with something for that long.

See, sharpness is only the first factor. Cleanliness is another. As you build up soap residue, microscopic cells, etc; the razor not only cuts more poorly, it's likely growing bacteria for you. There's ways to prevent that. Make sure the razor is as clean after use as possible, then dry it thoroughly. Some folks recommend rinsing them in something like barbicide, but I tend to see that as causing extra work for diminishing returns, so I don't recommend it when this comes up.

If your razor is sharp and clean, you'll minimize irritation as well as minimize and bacterial growth afterwards, which is what pimples are, and why ingrown hairs look like pimples. It's bacteria that's gotten part way into the skin and is being walled off and killed. The pus is dead microbes and your own immune cells (basically, this is the quick and dirty version because this is about shaving, not skin infections).

Next, you do your prep. The skin itself is going to respond best, overall, when it has been exfoliated gently, and is both warm and as hydrated as is reasonable. So wash your face first, with warm water. Not cold, that's going to cause issues.

Look, my hands are killing me, so I'm going to have to take some meds and come back to this. I will though, and I promise you that it'll be worth it. If you run across this before I come back, I intend to ping OP once I finish it. If anyone else wants a ping, let me know. It shouldn't be half an hour or so before I come back to it, but I will come back.