Geraldine, seventy, really wants a boyfriend. She has not had one in maybe thirty years, maybe forty. When she turned sixty-five, she decided that “it was time to start looking more seriously.” She bought a series of tickets to a local theatre; she decided to go alone hoping to meet someone else who was going alone. In her mind, this was the perfect strategy to meet someone who is likely to be compatible. Sure enough, she meets someone while she is waiting for them to open the doors for the show to begin. She encourages him to continue the conversation at intermission. He does. After the show, they chat again. She asks him for his phone number and his email address and she gives him her contact information. Geraldine felt like she scored. She, not wanting to wait around, called him the next day and left a message. A few hours later she received an email from him informing her that he wants no more contact with her. “Did I miss all the social cues?” Geraldine asks me, befuddled. “Maybe,” I said. “It is also possible that he had some sort of internal dialogue which you had no way of knowing,” I continued. “It is hard to live with the uncertainty of not knowing, because your mind goes to a place which explains the situation, even though when it comes right down to it, you have to accept that you will never know for sure.” “I go to a place where I blame myself.” Geraldine says. “Yes, you feel bad about yourself most of the time, so it is not surprising that when you have no other explanation, you assume you did something wrong. It is like a child who blames herself for her parents’ divorce.” I say, trying to point out that she is projecting her bad feelings on to this stranger, and that is one reason dating is so challenging. “Maybe I will figure it out when I am a hundred,” she says, lightening up the tone, but with a touch of fear about her age.