Tags » Overthinking It

On Enablers

50 Shades of Gray owes its popularity to the Kindle, and dubstep would die without iTunes.

Now, these don’t need the technology. You could read 50 Shades in paperback, and you could listen to dubstep without headphones. 228 more words


It Came From The Search Terms: Cold November Rain (aka Freezing Jerkwater From The Sky)

Every month we answer the things people typed into search engines like they are actual questions, adding punctuation but leaving the wording intact. If it sounds like me saying “but you could just not” 20 times in a row, that’s pretty much what happens every month with these. 1,722 more words


#648: "On dates, I feel like I am making all the conversational efforts."

Dear Captain Awkward,

I’ve recently been making an effort to meet new people via online dating, and it’s been pretty great so far – I’ve met a few cool, interesting people who I enjoy hanging out and exploring potential romantic stuff with. 810 more words

Reader Questions

#647: "To bang or not to bang, that is (literally) the question"

Dear Captain Awkward,

I may or may not be in love with my best friend. We have been close for over 10 years, and dated briefly at age 18, 8 years ago, when we broke up due to long distance and the mutual feeling that we both needed to have college experiences and relationships and sex, and to develop individually as people. 714 more words

Reader Questions

#646 "I feel guilty about quitting a job I have hated for the last 10 years."

Hey Captain and Crew,

I’ve got… well, let’s say I’ve got some guilt on how I handled a situation, and I could really use an objective perspective. 1,154 more words

Overthinking It

#641: "The Eli Roth-level torture of interacting with former coworkers."

Dear Captain:

Earlier this year I was asked to resign from a job in my preferred niche area of my profession, which was a devastating experience. 926 more words

Reader Questions

#638: I came out to my coworkers as a lesbian, how do I tell them that the partner I keep mentioning is actually a dude?

Closing comments because, WTF, people? 

LW, your coworkers are not going to care about this that much. It’s gonna be fine.

Hi Captain!

I changed careers and started a job in a brand new field about a year ago.  744 more words

Reader Questions