#275: “How do I keep a friendly (or more) connection with the guy who just broke up with me (twice)?”

Dear Captain Awkward, About six weeks ago, the guy I was dating (let's call him StarTrekFan, our mutual love for Star Trek and other geekery brought us together), broke things off very suddenly. I asked him to give us another chance and he agreed. We had talked about what issues had arisen and wanted to … Continue reading #275: “How do I keep a friendly (or more) connection with the guy who just broke up with me (twice)?”

#184: Confusing dude is confusing. Should I reach out to him and tell him how I feel?

Oh Captain, my Captain-- I was in a serious relationship with a man, let's call him Ethan, a few years ago while we were both in college. We met through our ROTC program. He was a very good guy, and a great boyfriend. I broke up with him around our one-year anniversary, because we rarely … Continue reading #184: Confusing dude is confusing. Should I reach out to him and tell him how I feel?