I call this the Tiger Woods problem... why throw it all away for flings with pornstars? Basically no one loves 'him', just his image and brand. I'm no Tiger Woods, but here's my 2 cents in case it helps you at all.

I'm pretty much where you are... as I've gotten older and more successful I've become a more attractive package, but I've learned more and more that women aren't into 'me' at all... just what I have. Over time this has hurt me and I now have major trust issues with women.

I recently took several years off from dating. Told myself I'd meet people organically in and around town. I wasn't looking to date, wasn't looking for hookups, just looking to get to know someone and do activities with them and see if we could act as friends. Asking myself: can I even be friends with a women? I should add I live on a lake, so there's a lot of "lake life" around here, lots of people to meet and have fun with, especially in the summer.

I've pretty much learned that just being friends with women and not sleeping with them doesn't change much of the equation. Women can still "smell" the success on me, and stick close largely because they are either 1) using me to have fun with my money/toys or 2) biding their time looking for an eventual in, or some combination of the two.

Overall I don't feel the majority of these women were good friends, or treated 'me' particularly well. I was a means to an end for them.

You think point #2 above (biding time) would be ok, but the reality is that these women got jealous etc even though there was no relationship between us (no sex, no affection etc). They acted as if they deserved some sort of claim on me, which of course was ridiculous as I wasn't taking anything from them other than their time. In some ways I think "just friends" messes with a woman's mind.

Long story short, because I wasn't seeking sex or anything it left me strangely feeling more used overall, as there was nothing I was taking in return for giving them access to my life/money/etc. I was giving the same, but getting less. They were still playing the game and trying to get things out of me, everything but getting to know or invest in the real 'me'.

I've come to the conclusion that men and women really can't be friends at all (at least, not when you're trying to find and build a real relationship).

Since that experiment, I started dating again, and can honestly say the gold diggers have gotten more numerous and more brazen. So what I do now to protect myself

- make a quick decision as to whether or not I see any long term potential in the person, the sooner the better. Drop them the moment your gut says no long term here. I don't want my time wasted, or theirs.

- I'm no longer sleeping with women until I've made a decision that there might be potential in the relationship (some ability to build trust). Easier to gauge long term potential without sex in the way (sex seemingly fast-forwards intimacy, but in a fake way).

I can say it's been successful. I met a woman who comes from a similar place in life (successful, but with trust issues) and so neither of us needs anything from each other except the ability to build a trusting relationship.

The word caliber comes to mind. If you're successful, you need to find women that match your caliber. Some form of success (doesn't have to be career or monetary) indicating they can meet you where you are.

Lastly, I miss the ability to trust. I often miss the love I had for my unhealthy first wife, because even though she was terrible for me, she loved me when I didn't have two cents to rub together. I never doubted she loved 'me' as a person, not what I had. Hoping to get this back someday.

Good luck to you