#1263: “I apologized and it made everything weirder. What’s really going on?”

Dear Captain, I've looked in the archives for something like this, but I couldn't find anything. What do you do when you apologize and it seems to upset someone even more? I (she/her) have an ex (he/him), and we have recently reconnected after a breakup and period of no contact and are trying to be … Continue reading #1263: “I apologized and it made everything weirder. What’s really going on?”

#1251: “My friends are mad because I don’t like talking in the dreaded Group Chat from WhatsApp Hell.”

Dear Captain, I looked through the archives and I couldn't see anything on this particular topic, but apologies if I missed something. It does seem connected to the Geek Social Fallacies though. My question is about how to deal with awkwardness and anxieties over the dreaded Group Chat. I have a group of friends who … Continue reading #1251: “My friends are mad because I don’t like talking in the dreaded Group Chat from WhatsApp Hell.”

#1220: “Is this guy constantly texting me after I told him not to because he ‘doesn’t understand’ boundaries or because he doesn’t care about them?”

Dear Captain Awkward, I ( 27, she/her) have an acquaintance (29, he/him) who is not neurotypical (he told me this). His preferred mode of communication is texting and he frequently tries to have long, involved text conversations with me. I was pretty tolerant of this at first, but it’s gotten a bit wearing. I’ve told … Continue reading #1220: “Is this guy constantly texting me after I told him not to because he ‘doesn’t understand’ boundaries or because he doesn’t care about them?”

#1211, #1212, #1213: FeelingsCourt Is In Session On Several Accumulated Matters Of The Heart

I have some questions about romantic feelings and dating and breakups accumulating and I don't know if they all belong together, but maybe they don't all need separate threads? I think what they might have in common is people who are trying to rules-lawyer their own hearts. Let's find out! Hello Captain Awkward, I'm not … Continue reading #1211, #1212, #1213: FeelingsCourt Is In Session On Several Accumulated Matters Of The Heart

#1209: “Is there a way to get good at setting boundaries that isn’t so situation-specific?” (Boundaries School!)

Hello, Captain! Could you talk about how to be good at setting boundaries in a non-situation-specific way? You get a lot of letters from people who are having trouble with someone else not respecting their boundaries, and obviously that is not the time to say "are you sure you really communicated what you meant?" But … Continue reading #1209: “Is there a way to get good at setting boundaries that isn’t so situation-specific?” (Boundaries School!)

#1208: “Question about Mom Friends being too Mothering:” BOUNDARIES SCHOOL is in session.

As promised...more "If you're 'not allowed' to say no to someone, they are not acting like friends" content. I have kept the Letter Writer's subject line as the post title so that readers too can have the "Wait, where is the part where this person is an actual mom" "Oh wait, phew, this person isn't … Continue reading #1208: “Question about Mom Friends being too Mothering:” BOUNDARIES SCHOOL is in session.

#1207: “I moved away from a roommate who treated me like her on-call therapist, but she won’t let go. How can I tell her ‘nicely’ that I don’t want to be friends anymore?”

This is going to be the first of a two-part series on how people who can't hear the word 'no' are not your friends. Hey Captain! I (she/her) just moved out of a group house. I lived with five other people in the house, including a couple (Elsie and Jenna). Elsie (she/her) and I are … Continue reading #1207: “I moved away from a roommate who treated me like her on-call therapist, but she won’t let go. How can I tell her ‘nicely’ that I don’t want to be friends anymore?”

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

#1168 and #1169: Friendship, Conversation, and TAKING TURNS

Here is #1168: "Is it unreasonable to want your friend to feign polite interest in your interests?" Hey Captain, I (she/her) have a close friend (he/they) who I've known for going on six years now. We originally met through real life things and bonded over having similar fandom-adjacent interests, although over the last few years … Continue reading #1168 and #1169: Friendship, Conversation, and TAKING TURNS