Pain or Boredom?

So, this comes with some thoughts I've had recently through some extracurricular crap that has been going on in my life and mistakes that I've made. I am posing this question: would you rather be alone and not felt anything or with friends, a lover, etc and feel everything, including the pain?

When looking back at my life, there are some definite 'I wouldn't change it if I had to' and there are the 'I could have dealt without having to go through that.' And so, I wonder if the pain is worth it? Obviously, it tells us we are alive and in a sense, connects us to one another; we now have the ability to empathize with another person, even if we will never meet them. Also, I wonder, does the pain make us more interesting? Art, theatre, etc would say so because happiness does not sell as well. The papparazzi don't look for happy couples; they look for dysfunction and we buy it. We buy a magazine about someone else's 'stuff' so we can forget about our own or so we feel better about ourselves. Shouldn't we spend that time instead fixing our own?

I guess in answer to my own question: I'd rather have a life of dark clouds for just the chance or just one silver lining than a life of emptiness and regret. 'It is better than to have loved and lost...' after all.