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

May 31, 2019May 31, 2019 ~ JenniferP ~ 78 Comments

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

#1200: “My mom is bugging me to clean my room.”

May 15, 2019May 15, 2019 ~ JenniferP

Dear Captain, About a year ago I was able to save just enough money to say, “F@&$ you!” to a really depressing living situation and moved cross-USA into my mom’s new house in the very expensive area near where I grew up. I’m lucky that my mom and I are fairly compatible personality-wise (and that … Continue reading #1200: “My mom is bugging me to clean my room.”

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

September 26, 2018September 26, 2018 ~ JenniferP ~ 467 Comments

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

August 3, 2018August 3, 2018 ~ JenniferP ~ 256 Comments

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

#1079: “Boundaries and ‘shoulds.'”

February 20, 2018 ~ JenniferP ~ 152 Comments

Dear Captain, I’m a woman in her mid-30’s who’s been dating a man a few years older than myself. We’ve only been together for about 6 months. Neither one of us has a very extensive dating history; he’s only dated one other woman, and I’ve only dated two other men. At first he seemed like … Continue reading #1079: “Boundaries and ‘shoulds.'”

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

December 16, 2017December 16, 2017 ~ JenniferP

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?

#1059: The reluctant pet-sitter (An ‘Art of No’ Post)

December 11, 2017 ~ JenniferP ~ 340 Comments

Dear Captain, This seems like a very minor thing to be asking for help with, I know. But I feel like even if there's no solution to my "problem", getting the input of a bunch of neutral parties (particularly neutral parties with solid understandings of boundaries) would make me feel better, and if you feel … Continue reading #1059: The reluctant pet-sitter (An ‘Art of No’ Post)

#1049: “Getting talked at by a fellow amateur writer.”

November 16, 2017November 20, 2017 ~ JenniferP ~ 156 Comments

Dear Captain, I write fiction, mostly fantasy. I admit I can be humorless about it. My friend “Shawn” writes fiction of similar genre. We used to talk about writing and about our ideas a lot, but less so since I got a day job. Shawn starts projects all the time and most of them never … Continue reading #1049: “Getting talked at by a fellow amateur writer.”