Date men and women from United States / Colorado / Greenwood Village, 40 year old

Date single man from United States. I feel as if I've spent months (o.k., maybe minutes, but it seemed like an endless process) trying to come up with a unique username and, yes, this is all I have to show for it. I hope I will be more successful in describing who I am and what I am looking for. I am returning to Match after a long hiatus. I have met some really fantastic women, including someone very close to being "the one". So I know success is a possibility, but also realize that the process can be painful and somewhat cringe-inducing. I've been on those dates where nothing clicks- I call them the "check please!' dates that can't be over soon enough. I've also been lost in conversation for hours and hours on dates that neither of us wanted to end. I'm hoping to find more of the latter, because it's a pretty good feeling when it works.
So, a little about me...I have many friends (at least that's what Facebook tells me) who would probably describe me as kind, funny, generous, laid back (sometimes a little too laid back), quiet (sometimes a little too quiet), intelligent and always there when needed. I've been in Colorado most of my life, though I was born in New Jersey (insert joke here) and went to graduate school there. I work in finance, managing money, but expect to put a stop to that as soon as I win the lotto, any day now. I have driven the same car for 13 years, not because I am cheap, but because it just won't stop running- so I guess you could describe me as practical. If you ask me to choose between camping and a hotel, I will choose hotel every time, but if you would like to camp, I will camp happily. Dogs really love me- I think that's a good sign. Cats and I have a very complex relationship- it remains to be seen if we can work out our differences. I respect you and your religion, but please respect my opinion that I have yet to hear an explanation of 'how/why we came to be here' that is to my satisfaction. If you can provide that, then you probably have a higher calling and shouldn't be wasting your time winking at me on Match. I am 'center-left' politically, but love the debate and might be convinced to move to 'center-right'. Extremes on either side, we might have a nice date or two, but in the end, it will probably do us in. I am an older man that knows entirely too much about "The Hills" and "The Real World", I'm not sure what that says about me, but I'm fairly certain it doesn't say anything good. I am well aware that my time would be better served by saving the world or curing cancer, but sometimes you've just got to let the brain rest. I sleep on the left-side of the bed, so I need someone who is right-side compatible. I can't share a toothbrush, even if its with someone I love. I don't know why, that's just how it is. I can do fine dining or a food cart on the side of the road with equal enthusiasm, but try to avoid Chilis/Applebees/MassMediocrity Inc. Collectively, this is who I am, with a few blanks left to be filled in, if you are intrigued please contact me. If not, thanks for stopping in and taking a look.
About her: Looking for beautiful, intelligent, successful and independent woman. Someone who will challenge me to be better in every way, but also accept me and the flaws I am inevitably going to show. Above all else, however, she will be willing to move to Italy immediately after I win the lotto...