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Tag Archive | romance

#551: What does it mean when a dating partner is “worried that they might be using me?”

Dear Captain Awkward, I’m a white ciswoman in my late twenties living in the Midwestern US. I’ve had a free online dating account for a while, having marginal success with short term dating but nothing that’s really led anywhere. My only *serious* relationship ended five years ago, after less than two years. I’ve come to […]

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Guest Post #499: Muddling Productively In Search of Romance

Dear Captain Awkward, I have a pretty simple question. How do I nurture my own sense of romance? A bit of background: I’m a twenty one year old queer girl. I was born in Mississippi, though I spent my teenage years in the north east. I’ve never dated a girl because of my own issues […]

#458: Things are great, so we don’t have to ever talk about feelings, right?

Dear Captain Awkward: My boyfriend and I are in our mid-twenties and have been together for about half a year. He treats me well, takes an interest in what I do and enjoy and is generally a good boyfriend. We have a lot of similar characteristics and the same silly sense of humor. When we […]

#300: My relationship is awesome y/n

Hi Captain & Team Awkward, I’ve been enjoying the site for a while now and have been able to take quite a few pointers from y’all, so thanks!   I guess the shortest way to ask my question is this: What are the green flags in any (budding) relationship?    Best wishes – Looking Forward […]

#293: Love! Movies! Adventure!

Dear Captain Awkward: I’ve always been one for bundling, so I thought I’d bundle 3 for the price of one :) I will also try to make this as compact as possible. #1 — I am a 19 year old guy, almost 20 in June. The first problem is that I have never kissed a […]

#279: “Help, I’m in love with my best friend and I don’t know what to do.”

Dear Captain Awkward, I’m in love with my best friend. That sounds like a really lackluster problem, but it’s really starting to weigh on me in a way it never has before. I’ve tried to talk to some other friends about it, but they don’t really seem to count as outside opinions (our friends are […]

Reader question #37: Overcoming lust and second thoughts to set boundaries with an ex.

Hi there, Captain Awkward, how are you? Brief (ish) back story. I dated this guy for ~14months. I think he was the nicest guy I’ve dated since my relationships moved beyond simple kissing. It was comfortable, and mostly happy. Then my parents separated whilst I was in the process of moving cities as part of […]

The Year of Living Awkwardly

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 […]


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