Minimally. Many young women worry about pain from tearing a hymen. Surprisingly, many women don't even notice any discomfort when using a tampon or having sexual intercourse for the first time. Additionally, you may have broken your hymen without realizing it through tampon use or vigorous activity (bike, horse riding, gymnastics, etc). If you have concerns or are worried, discuss this with your doctor.
Usually not... It is a relatively thin membrane in the vaginal canal and most females don't even know when it being torn. I.E during first relation or tampon use/vaginal exam/pap with speculum etc... Some discomfort is common, but if you have excessive pain, consult your doc... Good luck.
To variable extent. May hurt very little. On the other hand can be quite painful. Depends upon your pain threshold, thickness of your hymen and how it gets torn.
Not the guy. I will share this with some gynecologists and pediatricians for more information.