#906: “Anxious that my mom might try to connect me with an old schoolmate.”

Hi Captain, I realize my problem isn't as serious as other letters you've answered, but I figured I should try writing anyway since I don't really have anyone to talk to about it. I was friends with someone I’ll call “Oakley” from elementary school through high school. It was very rare for my parents to … Continue reading #906: “Anxious that my mom might try to connect me with an old schoolmate.”

Question # 147: “I handle myself badly in large groups of new people.”

Dear Captain Awkward: Most of the people who know me would consider me a pretty outgoing person, and with people I know/am comfortable with, I am quite extroverted.  I also think I'm pretty well-spoken and a decent conversationalist when I'm among friends.  But, when I'm in a social setting with more people that I don't know than people … Continue reading Question # 147: “I handle myself badly in large groups of new people.”