Q and I 

Your question; Is to have had and lost, better than not having at all? 
My answer; 

He who has had and lost has gained perspective, worth more than his initial possession.
Regret and loss do not necessarily come hand in hand. Regret is the desire for what could have been, or what was, so it is–must be those who have never had, and those who have regressed with the most regrets. 
Not every loss is a regression,yet some may progress with regrets, but my response may well be of no use to you, as this is a truth, only observed from my point of view…

Oops! ….I’m talking to my self again.

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