Tags » Overthinking It

#1048: The Unbearable Awkwardness of Dating

Dear Captain Awkward,

I am a woman who met a guy online a month ago. He is really good looking, funny, shows interest in learning more about me (sadly uncommon!), and gets along with my friends. 1,045 more words

Reader Questions

#1042: "How do I tell an old friend that I'm not interested in reconnecting?"

Dear Captain Awkward,

I have an awkward social situation that I’m not sure how to handle. It’s been causing me a bit of anxiety, and so I’ve been avoiding dealing with it. 1,015 more words

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#1040: "I matched my dysfunctional brother-in-law up with a dysfunctional friend and now they are ruining my holiday plans."

Dear Captain Awkward:

Please help captain! (I really struggled getting my letter to around 400words – there is a lot more detail if you need it… 960 more words

Reader Questions

#1037: "What should I do when the guy I like ghosts on me?"

Dear Captain Awkward,

I’ve been dating this guy for 3 months now. He has this pattern of disappearing for a couple of days and then come back. 1,462 more words

Reader Questions

#1030: Politely walking away from sales & conversion attempts.

Hello Captain!

This is a weird position I have found myself in.

I go to a lot of events, and I’ve noticed the people I go with or see there try to convert me to their lifestyle which heavily feature said events. 599 more words

Reader Questions

#1029: "I know this relationship is over, why can't I let go?"

Dear Captain,

I am currently with someone whom I know is completely toxic for me. He’s selfish, emotionally unavailable, dismissive of my needs and feelings, and apparently very depressed due to recently losing his career and having trouble finding a job. 2,800 more words

Reader Questions

#1027: How do I handle a hands-off advisor who expects me to be a mind-reader?

Dear Captain,

I am a 4th year PhD student in a STEM subject and I feel that everything has gone off the rails, in part because my adviser and I don’t communicate well. 3,854 more words

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