Tags » Overthinking It

#1025: "So Christmas lists are awkward, yes?"

Dear Captain,

This is probably a lot more low-stakes than a lot of other questions, but I’d like to get your perspective on Christmas/wish lists. 1,484 more words

Reader Questions

#1020: "Is this relationship doomed or do I just need to put in more work?"

Hiya Cap’n!

I’ve been dating my boyfriend for just over three years, and after a stint of long-distance, the two of us have recently moved in together. 1,443 more words

Reader Questions

#1016: How do I nicely tell potential dates "I hate talking on the phone and I don't want to do it with you"?

Sometimes letters just stack up together in a sequence sort of perfectly. Thank you, Letter Writers!

Ahoy, Cap’n!

I am a frequent lurker, sometimes commenter, and I have a question that probably has a pretty easy answer, but as I am super awkward myself sometimes, especially in dating, I am struggling to figure it out on my own. 1,087 more words

Reader Questions

#1015: Touching, boundaries, and compatibility

Hi, and thanks for an awesome and helpful site!

My situation: I’ve recently begun a new relationship, and am experiencing some…friction. I’m having trouble telling how much of the issue is incompatibility, and how much is me being “rusty”/ungenerous/inflexible, and I would love some outside insight! 1,425 more words

Reader Questions

#1009: Persistence is grossly overrated in dating and romance.

Dear Captain,

I am a man and I have a problem: I’m a creep.

I’m 30 years old, and I haven’t had a whole lot of romantic experience. 2,641 more words

Reader Questions

A Genuine Job Application

I just found an old job application I wrote for a computer game company looking for a writer.

I never heard back from them.

The Letter… 762 more words

Overthinking It

#997: Anxious Parents & Freeing Yourself From Constant Contact

Dear Captain Awkward,

I did not grow up in a house that did conflict- I joke (but not really) that I wish my parents had fought in front of their children. 2,566 more words

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