Intellectually I understand my choices but when do I connect with my feelings.
it sounds to me like youre doing a good job of that in T, mr magnet. i dont think these changes (healing) occur over night, but neither do they happen with time alone.
suzn asked you a good question in terms of your feelings. i think for the most part we all want to feel safe in our relationships, accepted, and loved. intellectually its easy to see that an emotionally unavailable person isnt in a position to provide those things, so why would we effectively set ourselves up to fail and why does it seem to hurt so particularly when we do? why do we then do it again?
i think the reasons are unique to each of us, but there are many common, sometimes overlapping "paths". greeneyedmonster, tryingsome, and steelwork named some of them. i think one underlying theme tends to be an unconscious fear of intimacy, which we present as a certain emotional unavailability, ourselves.
in eighth grade, i was on the receiving end of a lot of bullying. i was at a new school with no friends and everyone was more or less a threat. i was lonely and isolated, and i retreated into my head a lot. needless to say ive struggled with confidence ever since. i also came out of that year with a pretty high degree of rescuing tendency. i had a new found sense of self worth in helping others with their struggles. i fell for a troubled girl early in high school, a close friend. the harder i tried to connect, the more my efforts with her were rejected, resented, hurled back at me. the pain was mostly internalized. subsequently, i chose similar kinds of partners; achieving a relationship with them and "winning" their affections was an emotional victory and boosted my self worth. when their affections would wane, or when theyd inevitably dump me, it hurt worse every time.
i was learning some lessons along the way. it occurred to me, to some extent, that i was choosing girls i had a lot of misgivings about in the first place, that id overlooked or ignored. i learned about boundaries (read the book on em!). i started to regain an authentic sense of confidence. i was attracting and attracted to healthier gals though i failed to connect with them

. there wasnt that spark, or i dismissed them as boring, or they werent ultimately interested. i think part of that "spark" was really a game of push/pull which i became determined to win.
to make a long story shorter, i found a gal my senior year who seemed different than my exes. lots of the quirks, lots of qualities that pulled on my rescuer tendencies; stuff i sensed we could connect over, but this person seemed much more loving and affectionate. sometimes too loving and affectionate even for me. that too was a powerful hook. i could keep my guard up while she seemed to fall harder, until i let it down. that was enough pain that i remained single for three years, generally terrified of the thought of falling for a girl and not trusting myself at all. then i met my uBPDex and the rest is history. what was safe about her? she liked me more than i liked her. she needed me, depended on me, immersed herself in my world and my ways, and expressed intense love for me. she was jealous and needy and clingy, and dysfunctional, all of which, for once, put me in a one up position, which also felt very safe; all of which was a powerful narcissistic hook. it was as if i could do no wrong, nothing to make her like me less or push her away. the result, of course, was ultimately the same.
it was at that point that i realized the common denominator really was me, but this was good and welcome news because i realized i had all the power in the world to change the dynamic, not that i was unworthy or unloveable, but that at the end of the day, i hadnt been true to myself. frankly, and not least of all, i realized i had a lot of misguided ideas about love and healthy relationships - i thought love was all an adam sandler movie

.
so thats my path in a nutshell, and it involves several of the dynamics others have mentioned. your therapist says your whole life has been about avoidance, aloofness, and attaching yourself to emotionally unavailable women. so whats your story mr magnet? what are the themes and dynamics and when do you think they might have started? thats the place to start making our path clear. once we do, coupled with self awareness, we are better able to start making healthier choices.