Tags » Overthinking It

#614: Saying "no, but thanks!" after a date someone set you up on.

Hello Awkwardeers,

I was recently on a double date with a family member, their spouse, and an acquaintance of said spouse. The family member sold it to me as a “try it out and see what happens sort of thing” but I’m not sure if that’s how it came across to the Acquaintance. 737 more words

Reader Questions

Instant Gratification Isn't Fast Enough

Radio Shack showed me that “instant gratification” is a crappy business model. 343 more words


#610, #611, and #612: Variations on Kissing The Boss

Dear Captain Awkward:

I have a really great job; creatively fulfilling, changing and full of new challenges and people. I’ve been in this job for a lot of my 20’s, and devoted a lot of time and emotional energy to it. 2,688 more words

Reader Questions

Your Kids Hate Using Money

Spending money might go obsolete. Think of the children! 459 more words

Overthinking It

When Programs Write Programs

Humans are crappy coders. If an AI ever exists, it will completely reshape how we use programs. 703 more words

Cyborg APps

#600: How do I "help" my friend (my friend I'm totally in love with)?

Dear Captain,

In essence, I absolutely adore this girl, but there’s someone else, and she has problems being away from home. As a disclaimer: this isn’t some crush, or the case of a naïve adolescent. 3,326 more words

Reader Questions

#599: It's awkward when I run into my former students. How can I get better at these interactions?

Dear Captain Awkward,

This question is not so much about a single major situation or a crisis as it is about a recurring, if minor, situation that I encounter again and again. 3,429 more words

Reader Questions