Dear Captain Awkward, I would like to ask for your opinion of a situation that is currently happening in my life, hopefully whatever you may say might give me another perspective. I have a crush on the most gorgeous boy, my family friend and we've always been friends. He had a crush on me once, years ago, but … Continue reading #581 There is no way to know in advance what will happen to your heart & #582 But sometimes there are things you can do to protect it.
Ahoy, cap'n! So, I'm a fairly attractive and well-socialized guy with a self-esteem problem that makes it difficult for me to assert even that I'm fairly attractive and well-socialized. For the most part I keep that under control, but romantic situations are challenging. Being fairly attractive and well-socialized, I don't have much trouble meeting women. … Continue reading #231: How do I learn how to say the right thing at the right time to people I’m interested in?
Hi Captain Awkward- Long-time reader, first-time writer, etc. I have a question that does not appear to be covered by your existing advice about asking guys out. I am currently a student (grad, not college, if that makes any difference) and I have a crush on my TA. I'd really like to ask him out, … Continue reading #224: Asking out the TA
Friday is my birthday. In lieu of presents, there is something I would like (many of) you to do for me. Given that A Shy Guy Caught My Eye is the most-viewed post on this blog so far, I'm guessing that more than one of you can relate to this comic: If you read and … Continue reading The Year of Living Awkwardly
Dear Captain Awkward: There's this boy. He's cute. He's also super-reserved. Do you have advice on making a connection with incredibly reserved, hard-to-read people? I am a lady, for clarification purposes. If you met him in a karaoke bar, your way is clear: Sing this song and then buy him a drink. I'm guessing that … Continue reading Reader Question #3: A shy guy caught my eye.