Six Degrees of Playgroup Dating

I live in a different world (and city) than most of my friends from school or childhood - which means once I had a baby, I moved to an entirely different planet. Lately, I've been trying to establish relationships with other women in playgroups, regular haunts (caffeine and wine merchants) and my neighborhood and it feels more like awkward pre-teen dating. 

One woman who I seemed to have a lot in common with was in both my yoga and library group and unfortunately, after catching her maiden name on our email list, I Facebook'd her. Turns out I'm fairly sure that we not only went to college together, but she has witnessed a few rum filled, i-need-a-guy-to-define-my-self-worth VERY public frat party screaming  matches with my emotionally unavailable ex-college beau (who is now getting married, Congrats [enter Irish name here]! You've presumably reached emotional maturity and/or found a woman young enough to assume she can help you get over Oedipus complex, ahhhh youth). I digress.

Suddenly, her friend potential plummets. I cannot possibly go out on a third date and face the "Where did you go to school/meet your husband/move to?" stage because at some point, the light bulb will go on or she'll discover my maiden name and then it will all come rushing back and she will no longer be able to picture me as a doting mother, but as one of Captain Morgan's victims of binge drinking. 

Damn. If only they had Match.com for playdates (the clean kind).