#828: Can you live with your ex? (Spoiler: Not this time!)

Dear Captain and Company, I recently finalized the ending of a relationship...I say finalized because I've been trying to break up with my ex since October, but she finally was able to accept it months later...no matter how many times I told her, "my feelings for you have changed," "I'm no longer attracted to you," … Continue reading #828: Can you live with your ex? (Spoiler: Not this time!)

#825, #826, #827: The Art of Losing Is Actually Pretty Hard To Master

A series of letters from people who are trying to disengage but don't know how. There's some really toxic addiction and abusive behavior described in some of the letters, so, know that going in. Hey Captain Awkward, This is the LW of #776. This time my question isn’t about dealing with Toby’s parents, but Toby … Continue reading #825, #826, #827: The Art of Losing Is Actually Pretty Hard To Master

#823: Another Day, Another Creepy Dude Who Doesn’t Deserve Friends

Behind a cut for sexual coercion and general ickiness. Ahoy there Cap'n, I require some assistance please. I have a male friend who I've known for about three years, after we met on a mutual friend's birthday trip. We kept in contact after the holiday and in the last year since he moved back to … Continue reading #823: Another Day, Another Creepy Dude Who Doesn’t Deserve Friends

#776: “How do I help my recovering friend navigate a visit with his abusive family?”

Hi Captain My best friend, "Toby" has been living in my city for about a year now and over that time he's gone from being homeless and alcoholic to having a sweet flat and ten months of sobriety under his belt. I'm trying to be as engaged in his recovery and support as possible because … Continue reading #776: “How do I help my recovering friend navigate a visit with his abusive family?”

#725: “How do I get out of the middle of a situation that I set up?”

Oh Captain My Captain: I'm running into a communications problem, and could use some advice. First the backstory: I live with my parents. My mother, who is nearing seventy, is having arthritis issues and needs a little bit of extra help around the house; generally more help that I can reasonably provide while being a … Continue reading #725: “How do I get out of the middle of a situation that I set up?”

#689: Did I overreact when my date told me a story about rape and then wanted to get me alone?

Dear Captain Awkward, I’m newly single, and getting back into dating. I went on a date last night with a guy I met on OKC. We met up at a bar, and he seemed cute and smart, and as we talked it seemed like we had lots in common! But about twenty minutes in, it … Continue reading #689: Did I overreact when my date told me a story about rape and then wanted to get me alone?

#684: My boss brought a machete to a disciplinary meeting with staff.

Oh, Captain, my Captain, I’m a lawyer, working at a small-ish firm in the Midwest. As a bit of background, my last job was at a non-profit, where I believed in the work, and loved my co-workers, but it was a bad fit. My old boss shredded my self-esteem, and my leave-taking was not entirely … Continue reading #684: My boss brought a machete to a disciplinary meeting with staff.