Disappointments in love: are we ourselves to blame?

Wisdom comes with age, right? But what about immunity against disappointment, and even heartache?
How many relationships have we found ourselves in, that when they fall apart, we tell ourselves, “I knew this was going to happen.” Well, if we forecasted its demise, or even its lack of sustainability, then why do we go there to begin with?
Except for my marriage, which going in, I naturally did not doubt its promise for longevity, I’ve since been in other relationships where I knew there were major obstacles at the start. My last two ex-cubs, by sheer virtue of our age and stage in life differences, were unlikely pairings, not to mention other obvious reasons. Did I recognize that the obstacles were there at the onset? Yes. Did I plow through regardless, hoping that love would conquer all? Probably. Was I still surprised and upset when my initial doubts proved correct in the end? Absolutely.
I’ve also had some false starts in the past few years, where I met a guy who I crushed out on instantly (infatuation fever is my chronic condition, and I accept it). We had a lot in common and shared the same values. One of them lived in Israel, but I convinced myself that we could “Skype it out.”  Another lived closer, on this continent, just a few hours away. “Give it a chance,” friends said. “At this stage in your life, and in his, it’s hard to find someone you’re compatible with. Who is nice. And who isn’t taken.” I think what they also meant, but didn’t voice to me was, “At your age, especially since you’re divorced, you have to be even more open to compromise (read: settle?).   
So with these hopeful mantras in mind, I decided these relationships must be worth exploring. Even though somewhere deep down I sensed they didn’t have legs to bridge all that distance (which goes beyond just the geographical.)  And after only a few months of feverish sexting and phone calls, those relationships (if you could even call it that) were extinguished as abruptly as they had been ignited.
So then why go there?  Is it (pop quiz!):
A) Hopeless romanticism: We think that if we try hard enough, if we love enough, we can overcome the barriers.
B) Fear that the right thing – the right click – will never come along, so we have to nurture the bird in hand, even when it’s a squirmy little f*cker.
C) Naïve optimism: a belief that we can inhabit the moment and just enjoy it (ie. the “you only live once” excuse.)
D) An exaggerated sense of our own resiliency, where we think, “I won’t get attached. I won’t be hurt. And even if I do, I can recover quickly.”
E) Lack of any other options calling, texting, or even thinking about us. So the compromised option is looking even more appealing.
F) All of the above.
You can probably guess which answer I’d pick. (Yes, a big fat “F,” like my 9th grade History tests).  I think it’s a combination of many factors.  And it doesn’t necessarily get easier with age or wisdom. The disappointments don’t hurt any less, but I know that at least for me, they don’t last nearly as long.  
A friend told me something that resonated with me, which she heard from her mother: “Love never killed anyone.”
Personally, I interpret that to mean: “Go there.”  Can’t we be optimistic and romantic, and embrace the opportunity for love whole-heartedly, regardless of apparent obstacles? As long as we are aware that they exist?
Because even if you think you know – you never really know if you don’t try. Right?