Quizzical

Dear Dr. Frankie,

I am realizing that I need some practice asking the right kind of questions on a date. I don't think I want to tell someone right away what I'm looking for, and then distrust them when they tell me what they already know I want to hear. I think I want to ask them questions to get to know them and let them be themselves.

Dear Quizzical,

Learning how to ask the right questions is something of an art form. While there are many things you are probably curious about, you certainly don’t want to come across as intrusive or inappropriate. On the first date try to keep things on the lighter side. Avoid obviously heated topics such as politics and religion. You also don’t want to bring up Debbie-Downer topics such as previous relationship failures, family drama, and unresolved childhood issues. Avoid revealing these personal issues for several reasons. People who discuss such personal topics on first dates are sending up ginormous red flags that they have poor boundaries and questionable judgment.

On the other hand, asking someone on a first or second date what kind of woman she is hoping to meet sounds like an appropriate question. I would suggest being honest, perhaps not terribly specific, when you are asked. By answering generally it is less likely you will find your date morphing into the ideal mate you just described ten minutes earlier. Do keep in mind, however, that it is completely natural to want to try and impress your date. In the animal kingdom there are mating rituals that involve spreading ones most beautiful and most regal feathers or singing a beautiful melody to attract a nearby mate. I think it's less about asking the right questions and more about letting things unfold naturally and seeing where they lead.