#1165: “(I think) my only friend won’t hang out with me because of a dead guy.”

Hi Captain, I (she/her) am 39 years old and haven’t had a real friend since I was 23. Due to numerous instances of abandonment and rejection before and since, I’ve developed a form of Social Anxiety where I panic whenever I think someone important to me might, well, abandon or reject me. I’m working on … Continue reading #1165: “(I think) my only friend won’t hang out with me because of a dead guy.”

#989: “Me, my girlfriend, and a giant red flag” or “I’m gay, so why are all these angry men still part of my life?”

This question contains abuse and stalker behaviors. Ahoy! So, my story is a little complicated i guess but ill try and be as concise as possible. For about 2 months now i've been seriously dating a girl i really like and was talking to her everyday for a little while before then. We are officially … Continue reading #989: “Me, my girlfriend, and a giant red flag” or “I’m gay, so why are all these angry men still part of my life?”

#965: “My mom wants me to be her #1 sounding board and support system about her troubled marriage.”

Hi Captain, I am an adult (early 30's) child of two wonderful people who are going through some turbulence in their marriage--that thing of having an empty nest/rediscovering each other/discovering they have communication issues that have just been sitting there for 30+ years and are now blowing up. They're going to get counseling, which hopefully … Continue reading #965: “My mom wants me to be her #1 sounding board and support system about her troubled marriage.”

#917: “How to set boundaries with people who think boundaries and hurt are manipulative? AKA Help implementing boundary advice?”

Hello, Cap and friends! I have a couple of questions about boundary-setting with people who don't believe in boundaries. The Awkward team's advice and scripts on setting boundaries have been so wonderfully helpful in my life, but what (if anything) can you say to people who believe that setting boundaries in a family is controlling? … Continue reading #917: “How to set boundaries with people who think boundaries and hurt are manipulative? AKA Help implementing boundary advice?”

#834: “My mom keeps gifting me with stuff that isn’t just stuff.”

Dear Captain Awkward, Now that my spouse and I have purchased a house, my mother (who is a difficult person, reminiscent of Alice, but with her own special nuances) is constantly sending us my family’s old junk. Here’s how the conversation goes: Mom says (for example), “I have all of these lawn ornaments that have … Continue reading #834: “My mom keeps gifting me with stuff that isn’t just stuff.”

#830, #831 and #832: Boundaries and the power of “no!”

Three letter writers who need some help saying "nope!" and making it stick. Dear Captain, I'm rapidly running out of patience with my housemate and am at the same time increasingly concerned about him, and I could really use an outside opinion on what, if anything, I can do to help him without damaging myself … Continue reading #830, #831 and #832: Boundaries and the power of “no!”

#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