Dear Dr. Darcy:
I am thinking of asking someone out who I've known for many years but there's a complication: I used to date her sister. Its even more complicated b/c the sister is younger and more attractive than my ex. You think this is a bad idea?
I’m trying to identify the words to express this delicately, but I’m concerned that delicacy might minimize the depth of the stupidity of what you’re contemplating, so I’ll do what I do best and be blunt.
I don't care if you dated your ex-girlfriend in 9th grade ~ unless you're still in 9th grade, the idea of dating her sibling is unacceptable and inexcusable. That you felt her sister’s age and physical attributes were the elements that ‘complicated’ your dilemma is, at best, baffling.
I’m going to invest a minute longer in your moral evolution so I can sleep better tonight: What if you took a different path and found yourself an unattached woman who is not a relative of your own or of any of the women who you’ve dated? What if you walked away from the above-referenced woman, knowing that you spared your ex-girlfriend of unnecessary pain? What if you found some other way to spin your need for drama, one that didn’t involve the pain and suffering of others? Do the world a favor and just contemplate these questions for a few days.