QWhile visiting my family for the holidays, my 72-year-old father informed me that a 29-year-old Russian woman was coming to America to be with him. He could hardly contain his excitement. Dad didn’t want me to tell my brother and sister, because he knew they would be critical of him being with a 29-year-old Russian virgin. He’s correct. They would judge him. But I couldn’t care less who he fucks.

Best of Chicago voting is live now. Vote for your favorites »

I have since had some conversations with my dad about the likelihood that a legitimate 29-year-old woman—or even a 50-year-old woman—would want to be with a 72-year-old man in bad health. There is nothing exceptional about him. He is overweight, basically lives on social security with enough left in retirement savings for some luxury in life, has no special talents that would make a much younger woman attracted to him, i.e., he is not Jack Nicholson, etc. I encouraged him to think about more age-appropriate partners and did some Internet searches for him on legit dating Web sites. He’s not interested in anyone close to his age. Those women are “old,” he says.

Should I help him with the dream of finding a much younger woman? Or, do I continue down the path of convincing him to seek out women who, if not age-appropriate, at least have similar life experiences? —No Fools Like Old Fools

Incidentally, for some reason after ten minutes of this bickering we were both still turned on and we ended up having sex again—and this time we BOTH got off! —Loaded Question

And who knows? If you play your cards right, JJ, you might get invited along. But if you act like a jealous, irrational douche bag, you’re definitely going to get your ass dumped.