Thanks for the input so far gentleman. Hopefully this thread can help others who find themselves in the same scenario. To answer a few questions:
There is a lot of talk on marrying her. I never mentioned the thought of that in the OP. One of the red flags I had mentioned though (marrying straight out of high school and getting divorced) may actually be an asset. She has already experienced marriage and knows how shitty it can get, as opposed to the younger, never married women who just "want a ring" and to live in marital bliss. If anything, I think this keeps her from wanting to repeat that cycle. Furthermore, I already told her that if she wants a ring or child anytime soon that I am not the guy for that. She claims that she is 100% okay with that, but we all know women...
The original post was to determine if I should continue this relationship or if I should be single again. As Noir pointed out, I am definitely romanticizing my player days. Grass is always greener. But it is measurable and obvious that I have regressed in the gym, hobbies, guy-time activities and am certainly paying the mental price now. As noted before, I am the leader and it is my responsibility to create balance in the relationship, not her --- So this is my fault.
In regards to the sex. It's good, but the passion lacks now. Could be low-T...familiarity...or some other type of mental slump I'm in right now. The old saying of "show me a beautiful woman and I'll show you a man who is tired of fucking her" certainly applies here. This could just be biological.
Normally I wouldn't post about this, but after a life audit i've realized that this is all i've ever done. Meet, seduce, relationship, bored, bye. Rinse. Repeat.
There has to be more to life than that, no?
Another well respected poster suggested that love is not the same as pity but I don't feel as if I pity her. Sure I may play a fatherly role at times and help her out with a lot of things, but I'm not sure as to if it's pity.
Regardless... here is my plan to get some answers:
1) I am packing my bags right now for a two week trip. East coast, NYC, midwest, then back. I can write half of it off for business as well. This will give me time to talk to hard hitters in my field, see my best friend (known each other since age 2 and grew up together), and attend a party of some of my close friends back in my home town. There will be booze, women, and most importantly, good conversation (I hope). getting in touch with my roots and seeing good friends should help to stabilize things, not to mention 2 weeks away from her to give myself some time alone with my feelings. Depending on how much I miss her (or how much I do not miss her) will be telling.
2) Upon return I'll restart a gym regimen and also get my vitamin and T levels checked. It's been a while since i've had blood work done and I know the cycles I ran in college were not the best decision i've made. What's done is done and i'll make the proper adjustments if there is a deficiency.
3) I'll continue checking in on the forum for more advice from you all. Some are not cut out to be in a relationship, others are not cut out to be players. Some, like me, don't know what they want or what makes them happy. I will need to find this.
4) I will be integrating hobbies back into my life. I signed up at a Yoga studio nearby that one of my clients works at (She supports my business and I will support hers). I'll also pick up a set of golf clubs and find my swing again. I'll make it a requirement to hit one networking/cocktail party per week (alone) to meet new people and perhaps find new clients/connections.
I believe, after implementing the following, the answer(s) should shake out. If not... Back at square one but just in better shape and have a new set of clubs.
Flight leaves in less than 24 hours