To love and lose, or not to love?

I'm having one of those days. The ones where you wonder about the choices you make, about how you got to where you are, and whether those decisions were the right ones. One of those days where you just wonder about life in general.
I think it's the weather. Gray, gloomy, etc.
One thing that's been on my mind lately is that age-old saying about how it's better to have loved and lost than to have not loved at all. Or is it?
You might remember a post I wrote back in October about how my girl TSwift would've been proud of me. I was just starting to date that guy, and we had a lot of fun until things ended six weeks later. It's been more than two months since then and I'm still hung up on that guy. Not in the ice-cream-pint-late-at-night kind of way, but hung up enough that my heart still aches for what might have been.
So is it better to love and have lost that love or not at all? I honestly don't know. I'd like to say yes, but at the same time... it's so hard having to look at someone and wonder how your life might be different now if things had worked out. Hard enough that maybe it's better to not love at all.
What do you think? If you've been in this situation, how do you deal? Or have you been on the other end of it, wishing you had loved and lost? xx
(if you're reading this, mom, happy birthday !)