Chapter 1: How it started

How far should a mother go to help her socially awkward son learn the ropes of dating? That is the question I faced when I saw how isolated and unhappy by 14-year-old son Andy was. It was October of his first year in high school. Couples were pairing off, and “group dating”was seen as childish and so “middle school.”

Jack, Andy’s best friend since 4th grade, wasn’t hanging out with Andy playing video games in our basement any more. Instead, Jack was spending time with Victoria, his new girlfriend. At lunchtime, many of the couples, including Jack and Vickie, sat together, leaving Andy feeling abandoned and alone. When he told me how much he disliked high school because he didn’t have a girlfriend, my heart ached for him. I imagined him sitting at the “nerd” lunch table, looked down upon by his former friends.

Worse still, when I asked Andy if there were girls in his class he liked and wanted to date, he told me several names. I knew most of these girls from the neighborhood and I realized that they were far beyond Andy’s reach. In fact, I feared that Andy simply lacked the social skills to be able to date any girl at his school. He was too shy to approach a girl, and he had no idea of what to say or how to act if he actually had the nerve to ask a girl out. And if she accepted, Andy on a date would be a social disaster. The result would further crush his already fragile self-esteem. So, what to do.

For my own part, when I was 14, I had no problems in the dating world. I was asked out by older boys, sophomores and juniors at my school, and a few of my dates could actually drive. Once a senior asked me out, but my parents forbid me to date some one so much older. But, I don’t think I ever actually dated a high school freshman boy, so I had no way of knowing just what Andy needed to boost his self confidence.

I talked it over with my husband, Peter. What did he do when he was that age, and how did he overcome the natural fear that 14 year olds certainly have in approaching the opposite sex. The answer was discouraging. Peter said he never had the nerve to ask out a girl when he was 14. He said he didn’t date at all until he was 16, and then he dated girls a few years younger than he was. So, neither of us had an answer to Andy’s problem as an awkward 14-year-old boy who wanted a girlfriend but couldn’t manage the social skills to get one.

Reading various Mom’s-circle forums online, I learned that one mother had taken the bold step of going on a “practice date” with her son to give him some self-confidence and some social pointers for dating. I thought that could be the solution for my Andy – a date with me. Peter agreed to my suggestion.