The first time I realized women were not experts at sizing up other women was when I asked a girl to hang out “in town” with me. At 15, I couldn’t drive, couldn’t afford a fancy dinner, but I could buy her an Italian ice at Gee Wiz. I had everything planned out. I’d walk to her house and then we’d walk into town together. (Maybe I’d even hold her hand or put my arm around her as we walked.)

Well, I received a text the day before our big night on the town, or I should probably say, in the town. She couldn’t make it. Her family had plans they didn’t tell her about and she was “soooo sorry.” I figured that made sense. My family had sprung plans on me out of nowhere before. So, I tried again. She couldn’t make it.

I figured I’d better not ask her anymore and told my mom the details of my failed dating efforts. She persuaded me to keep trying.

 “Something probably came up,” my mom said. “She probably has a good reason.”

Against my intuition, I asked for a third time and the girl even said she was looking forward to it, maybe my mom was right! Then the girl never showed.

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I sat in town by myself for twenty minutes, texted her, received no response, and walked back home, alone. Later that night, she texted me she didn’t have access to her cell phone and we should still hang out another time.

My mom told me to go for it again. I did. Same result. The girl no-showed once more.

I told my grandpa the story.  And he told me where I went wrong. 

“If a girl cancels on you once, that’s okay. Give her the benefit of the doubt,” he said. “If she gives you the run around more than once, forget about her and move on to the next one. “

If I would have known my grandpa’s advice sooner, I would have saved myself the embarrassment of my plans constantly falling through, the girl the effort of making up lame excuses for a date she didn’t want to go on, and my mom the annoyance of me pestering her about the awful dating advice she gave. I should have also known my mom probably thinks every girl in the world would want to date me because, after all, I’m her son.