#1040: “I matched my dysfunctional brother-in-law up with a dysfunctional friend and now they are ruining my holiday plans.”

Dear Captain Awkward: Please help captain! (I really struggled getting my letter to around 400words - there is a lot more detail if you need it ) My brother-in-law ‘Hector’ is 36 and ‘Agnes’ is his first ‘girlfriend’. I’d known Agnes for a few years before setting her up with Hector– she’s now 40 and her … Continue reading #1040: “I matched my dysfunctional brother-in-law up with a dysfunctional friend and now they are ruining my holiday plans.”

#950: “I’m newly sober. How do I brush off ‘Thirteenth Steppers?'”

Hey Team Awkward, This is a quick one.  I'm newly sober and I've been attending AA for the last two months. One of my main meetings is a women's meeting, which is rad, but I've tried to open it up a little bit--there's a co-ed secular meeting and a co-ed meeting that does a physical … Continue reading #950: “I’m newly sober. How do I brush off ‘Thirteenth Steppers?'”

#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.”

#897: “Every time I invite our friends to something, this person suggests a competing event.”

Hi Captain Awkward, I find myself in a very awkward but relatively low-stakes situation with a classmate. There is a woman in my cohort at college who has this weird habit of rescheduling other students' social events (not just mine, but mostly mine). For example, someone invites the group by email out to go hiking, … Continue reading #897: “Every time I invite our friends to something, this person suggests a competing event.”

#856: “Let’s totally do that thing together….sometime.” (Time, Planning, & Boundaries)

Greetings, Captain! Long-time lurker checking in with a relationship problem. My boyfriend and I (she/her pronouns) have a lot of different interests. Which is fine! Not all my stuff is his cup of coffee! Not all his stuff is my cup of tea! The issue is when he says he wants to do something with … Continue reading #856: “Let’s totally do that thing together….sometime.” (Time, Planning, & Boundaries)

#792, #793, #794, & #795: Variations on the Unfixable

You're worried about someone or something. You want to help. What happens if you don't try to fix whatever it is and take care of yourself instead? Dear Captain Awkward: My boyfriend and I have been dating for three years and I dread every interaction with his family. He's the youngest of five. The eldest … Continue reading #792, #793, #794, & #795: Variations on the Unfixable