Dear Jack, a smile flitted across my face as I read your mail. The conundrum you’re facing is what I call the Vanity-Charity syndrome: do you date your vanity or date love? Or as you put it, there’s this medical doctorâ€¦ and there’s this other girl who’s not a medical doctor. Who should you date? And while some will scoff at your question, the truth is, it’s an issue young men are often confronted with.