@Jack of no trades
You have a couple misconceptions in your post. F-stop is a measurement of the size your aperture, and as it gets lower, the opening of your aperture gets wider. This is why many photographers refer to at your lowest possible aperture as shooting wide open.
Second, bokeh is the out of focus section of the shot, which should not deter from the level of focus on your subject. In the bar shot, the D3300's picture looks softer than the iPhone's around people's faces.
On the portrait shot, not only does the Nikon have better focus and detail on the subjects, the creamy bokeh creates much better separation between the person's face and background. The iPhone's pic features a much more detailed background, which is actually somewhat distracting, while also being less sharp and detailed.
Jack of no trades :
As a less than amateur photographer, even I know that you don't describe f-Stop in terms of wideness. Add to the fact that sensor size must be taken into consideration when comparing f-Stop, and you'll see that the Nikon far outclasses the iPhone. And praising the Nikon blur (bokeh) in the portrait shot and then condemning it as not as sharp in the bar scene is at most contradictory, and at least uninformed. I'll stop here and let the experts continue...