Playboy Advisor

April, 2015

For our third date, I recently invited a woman to have drinks and dinner with me at a popular private social club. The day of our date, she texted me, "What should I wear?" I had difficulty answering this question for several reasons: One, a quick internet search of the venue showed photos from a variety of previous events; two, it didn't seem very romantic for a man to respond with phrases such as "dressy casual" or "trendy cock­tail"; three, I wanted to find out i...