Category: BREAKING UP

#1284: “I have to see my ex again in a year and it is a constantly ticking time bomb in my head.”

~ JenniferP ~ 117 Comments

Sometimes your brain just wants to be obsessed with somebody for a while. Hi Captain, My now ex (he/him), and I (she/her) broke up at the end of May. It was pretty much mutual. He asked if we could stop being exclusive for a while (we were long distance). I was already having other problems … Continue reading #1284: “I have to see my ex again in a year and it is a constantly ticking time bomb in my head.”

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

~ JenniferP

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?”

#1257:”How do I navigate the transition between romantic relationship and friendship with someone who’s really (platonically) important to me?”

~ JenniferP ~ 100 Comments

Dear Captain, I had a friend I first met about 15 years ago. We got on amazingly well: mutual friends called us “one mind in two bodies” because our personalities were so similar. We understood each other almost perfectly and could talk and laugh for hours about things nobody else quite got. We then had … Continue reading #1257:”How do I navigate the transition between romantic relationship and friendship with someone who’s really (platonically) important to me?”

#1254: “Does my micromanaging business partner / friend need to get a life, or have we mixed too much business with friend dynamics?”

~ JenniferP

Hi Captain! I (she/her/hers) am a business partner with Partner (also she/her/hers). We have been running a small business for a few years now. We had one employee who just retired, and we finally hired someone part time. We are equal owners in the company. We went to grad school together and I thought we … Continue reading #1254: “Does my micromanaging business partner / friend need to get a life, or have we mixed too much business with friend dynamics?”

#1250: How do I support my (very-recently) ex-partner through his complex grief?

~ JenniferP

Content note: Mention of suicide Dear Captain Awkward 2 weeks ago my boyfriend (he/him/his) of 2 years made the decision to break up with me (cis/female). I moved out of our shared house and back with my parents and sister. I did not want the relationship to end and I hoped we could have worked … Continue reading #1250: How do I support my (very-recently) ex-partner through his complex grief?