Does it hurt more to have someone and lose them, or to never have them at all?

It hurts more to have someone and lose them than never having "that someone" at all. Because when you have someone you get attached and that person becomes a part of your life. Losing him/her feels as if you're losing someone who once belonged to you and when you feel the person going away it has a direct impact on your life. It hurts a lot and it takes a good time to heal the pain of separation. It happens when we cling to someone. On the other hand, if you never had "that someone" at all, there is no point of attachment or separation. You might feel bad for not having that person but it won't hurt you that way.

I would say both but they have completely different feeling. Having someone can hurt just as much as not having them. you can feel emptiness not having them and heart broken but you can also feel not good enough and insecure when you do have them.

It always hurts to lose someone -- but if you at least have them for a while you get to grow + nurture your own life with the light they bring to it. In my experience, anyone worth crying over was worth having in your life. You're missing them because they made a difference.

You meet people for a reason, they have a purpose in your life. They will teach you things that will help you be a better person. Some will hurt you, others will love you, but whatever it is, they are the reason of who you are today. And if you lose them it means their purpose is done. So its better to lose someone, learning than never learn at all.

to have someone and lose them it teaches you things you would not of understood before. which in result makes you a better person overall

It may hurt more but it also help/please more. One may find that having never loved or tried, that there is despair in not sharing life with others fully. It take energy to live life to its fullest, love and take risks but there are also pain in too much introversion which can lead to a cycle of negative thoughts and despair.

This is a very subjective answer. In my own opinion regrets of doing something is lighter to carry than regrets of not having done it. They say it's better to love and get hurt than to never love at all. It is a universal truth that a time will come that we will lose someone. It is painful. That's why we try to find someone who's worth that pain. So even if we are hurt, we have no regrets at all.

Both hurt but the intensity of each and which depend of the individual. But at least, in my opinion, having someone and losing her/him provides at least some kind of experience.

To have someone and loose them, because you become connected with him/her and when you lose him/her you loose all the happiness from your life

I would think if you never had them at all, you wouldn't get hurt. But life's all about taking risks. We're all going to get hurt at some point or another. It's inevitable unfortunately! But we can use all moments in life, even the bad ones, to grow and learn more about ourselves so that we can be our own personal best.