Post a few examples with the EXIF intact and it should go a long way toward helping you. 35 will look much different than 85, and if you're seeking highly blurred backgrounds, going to a wider lens is going to make that harder.
Without seeing the images, the general suggestion would be get their eyes on the same plane relative to the camera, if they're not in focus then put more separation between yourself and them and them and the background and refocus. Putting them further from the background will help you achieve the same background subject separation. Again, seeing where you're at with the images and what kind of room you have to work with can change that.
Also work off of what you see in the images. The DOF calculators are an approximation, and from what a little searching will turn up, you'll see they work on a model that implies less DOF than there usually is in practice. Also it's important to keep in mind the distortion of the lens at the wider angles.
In practice I've found that f4-5.6 is plenty for small groups, for larger groups I can start at f8, f2 is more for individuals unless I'm using a larger working distance.