It Came From The Search Terms: The Last Day In May

Hello gentle friends, it's time for that thing where we treat the things people typed into their search engines to find this place as if they are questions in their own right. As is traditional, we begin with a tune: https://www.youtube.com/watch?v=Hi5A9OCAyIk   Then we begin the no-context guessing games and assumptions! 1 "Adult male using … Continue reading It Came From The Search Terms: The Last Day In May

#1147: “My lover wants me to keep our relationship secret from his ex and kids.”

Hello! I'm sorry, this is complicated. I am in my late thirties and have fallen in love for the first time in my life. We have been in love for a year. I believe he is the love of my life, which I have never believed about anybody, and he believes that I am his. … Continue reading #1147: “My lover wants me to keep our relationship secret from his ex and kids.”

Short Answer Friday/Chat – August 3 – Pledge Drive Concludes

Hello, it's on! Patrons can submit questions here (advantage: 1st dibs, more words). Anyone/Everyone can submit on Twitter (@CAwkward, #awkwardfriday), questions close at noon Chicago time, I answer as many as I can and update as I go between noon and 1pm. Whatever I don't have time for gets held over for next week. Comments … Continue reading Short Answer Friday/Chat – August 3 – Pledge Drive Concludes

#1063: Is this all-in-good-fun old-timey-cosplay flirting or weird boundary-pushing flirting?

Dear Captain Awkward, Four years ago, the first fling I had after I left my ex was with a guy at a large multi-day costume event in a far-off state. He came on really strong (in character) and as we have friends in common, I knew he was engaged and asked him about this. He … Continue reading #1063: Is this all-in-good-fun old-timey-cosplay flirting or weird boundary-pushing flirting?