Category: Dating

#1246: “Partner with lots of expenses and little income.”

~ JenniferP ~ 1 Comment

Hey Captain Awkward. I read some of your responses to other writers who had concerns about their partners’ finances, and I feel like this is related but not quite the same. I’m stressed about my boyfriend’s money management skills and how I can help him without getting myself into a bad financial situation. I also … Continue reading #1246: “Partner with lots of expenses and little income.”

#1225: “My boyfriend is very reactive to conversations about feelings.”

~ JenniferP

Hello, I've (she/her) been dating my boyfriend (he/him) for one year now, we are both in our late 20s and sadly both still living with our families due to student debt. For context, we also both have anxiety and he struggles with depression. It can be very difficult for me to bring up any issues … Continue reading #1225: “My boyfriend is very reactive to conversations about feelings.”

A++ Recommend! Scarleteen’s “Embracing Newbiehood: How to Approach Dating and Sex in Your 20s With Little or No Experience”

~ JenniferP

This piece written by Cass Ball is great. And you can safely replace "20s" with "any part of adulthood." Now's the part where I physically restrain myself from quoting the entire thing: "When I’m coming from a place of scarcity, a place where everything feels like it isn’t enough,I often feel that I’m insufficient without … Continue reading A++ Recommend! Scarleteen’s “Embracing Newbiehood: How to Approach Dating and Sex in Your 20s With Little or No Experience”

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

~ JenniferP ~ 144 Comments

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

#1206: How do explain that I’m almost-but-not-quite divorced in my brand new dating profile?

~ JenniferP

Hello Captain Awkward, Last month my husband and I (she/her) separated; it was my choice and I stayed in the home while he moved out. We were in couple’s therapy for several years leading up to the split and for the last part of the relationship we were living as roommates. For almost the last … Continue reading #1206: How do explain that I’m almost-but-not-quite divorced in my brand new dating profile?

It Came From The Search Terms: The Last Day In May

~ JenniferP ~ 78 Comments

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

#1196: “My friend is irrationally jealous of every woman who speaks to her boyfriend and I’m tired of it.”

~ JenniferP ~ 189 Comments

Dear Captain Awkward, Short Version: I (she/her) have a friend (she/her) who is irrationally jealous of her boyfriend, and it's driving all our friends apart. I don’t know whether to try help her, or just to distance myself from our friendship. Longer explanation: She and I have now been friends for about five years, including … Continue reading #1196: “My friend is irrationally jealous of every woman who speaks to her boyfriend and I’m tired of it.”