couple things...this last encounter only lasted a few months. please make sure not to define yourself by it. you met somebody and it didn't work out. PERIOD. going into all THEIR faults doesn't help you in the now.
second, there are more options than PERFECT or TRAIN WRECK. if you feel you MUST re-engage in the social scene, try to do so with an open mind...and NOT seek the perfect other. (there isn't one). give it as much impact as shoe shopping or ski boots, trying on different colors and styles to see if anything fits, but knowing that sometimes what SEEMS to fit in the store, hurts your feet or calves later.
third, i noticed you said "meet for drinks" each time in reference to the potential DATE. maybe expand your horizons and not have it center around a bar or alcohol. think outside the box. make it fun light and carefree.