Monthly Archives: March 2012

Mr. Emerson & Lucy from A Room With A View

"I don't believe in this world you?"

Dear Captain Awkward:

I think I may have messed things up with my amazing boyfriend, and I just feel terrible about it. Let me preface by saying that I am 19 and he is 20, about to be 21, and we have been dating for just over 3 years. We met in high school, and have continued dating into college (we go to the same state school). I love him to death, he brings joy and light to my life and makes me incredibly happy. We’re very different people, but opposites attract, he brings stability and logic to my life and I bring whimsy and eccentricity to his. We’re compatible in so many ways, the word “boyfriend” doesn’t do him justice, after 3 years together, he feels more like a partner (if that description makes any sense), and is as much a part of me as I am of him. Some people may say that I am too young to be in such a serious relationship, and that I’m “missing out” by not dating around, but I do not feel that I am missing out on anything, and I couldn’t imagine my life without him.

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Dear Captain Awkward,

So there’s this guy, let’s call him James. We have been friends for several years and in this, our last year of medical school, have slowly gone from drunken making-out, to friends with benefits, to casually dating. It has been exciting and awesome, but we were both more or less expecting this part of our relationship to be temporary since we assumed we would be moving to different cities for residency. We agreed it would have been foolish to enter the residency match as a couple, since we were just starting to explore the attraction back when that decision had to be made.

Against all odds and without any attempts to manipulate the system, we matched in the same city, my hometown. We’re not sure yet if we are going to keep dating – the removal of a definite end date means we now have to consider long-term compatibility in a way we haven’t before (God, I sound so clinical. I have emotions, I swear). I don’t want to spend time in a relationship that doesn’t have at least the potential to be forever, so we have started talking about what we both want in life. I feel good about all of this. Worst-case scenario we keep having fun until graduation then move to the new city as really good friends.

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First, I love this: How do work up the courage to kiss the girl I like?

Second, a letter:

Hail to thee, O Captain,

Perhaps I’m taking a different approach than other letter writers, but I would like your thoughts and judgment on events that quickly transpired this weekend. I had little time to deliberate, and ultimately chose my course of action without advice from others, and now I would like to know whether I was justified in my actions, or whether I erred.

To briefly explain my circumstances, I’m a professional student in my mid-twenties, and was in a passionless long-term (three years) relationship until last year. Following that commitment ending, I’ve sought to expand my opportunities at meeting new partners in the adventures of the online world. I don’t think my experience there was atypical, and I met many nice people, but few who would commit to anything beyond one or two dates.

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Dear Captain Awkward

I have two friends, let’s call them Jane and John, who have been in a long distance relationship for the last few months. She’s 18, he’s 25 and they met online – same way I met both of them. They decided to meet face to face but at the last minute Jane freaked out about it and called it off. The reason she freaked out is because she has decided that if he meets her “in real life”, he will find her disgusting (her exact words) and dislike her, and even if he doesn’t break up with her that’s only because he’s too nice a guy.

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Dear Captain Awkward,

I’m sure there’s a short and sweet solution to this one, but I can’t seem to see it. Perhaps the Awkward Army can advise?

The very short version: There’s a guy, and he’s cool, and I’d like to maybe get coffee with him sometime and see what happens.

I know, I know, I should use my words! And ask him to get coffee sometime! And do it soon, before I become all invested in a supercrushofdoom! And not hang around becoming friends and nursing a secret crush in the hope that he’ll get a crush on me too!

The reasons I haven’t done this are because of the slightly longer version of the story:

Cool guy is a newish addition to a group of loosely connected awesome people that make up a lot of my social network. Within the broad, loosely connected group, me and two other awesome ladies form a bit of a trio of close and hilarious and got-each-other’s backs friendship.

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I’m happy to say that this is my most pressing question about sex ‘n’
relationships ‘n’ stuff right now.  The short version is that a lot of
people who don’t know me that well aren’t sure whether I’m lesbian,
straight, or somewhere in between.  I’m sure where I am (straight) but
I also like the protective shield that uncertainty gives me against
unwanted (male) advances. (The unwanted female advances are rare and
flattering.) But now I’m wondering if this is kind of a shitty thing
to do, knowingly allowing people to draw the wrong conclusion instead
of being honest about who I am, just so I can avoid a few passes.  I
also worry that I am missing out on all the guys who don’t want to be
so gauche as to hit on someone who might be a lesbian.


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Dear Captain Awkward,

I’m 24, a lady, and I have never been in any kind of a romantic relationship before, until now. I think I’m fucking everything up. Here’s the lay of the awkward;

Some mutual friends of ours set me up on a blind date about a month ago and we really hit it off, or at least he really did and I kind of did. I enjoyed our first date which was just talking, and our second time hanging out was at his apartment and was just making out, I wanted to do it and it, and I was probably no kind of good considering this is the first human penis I’ve gotten to know. But after that, that’s all our relationship has been, arrange to hang out at one or another of our places, delightful sloppy make outs that end when he comes, and then cuddling and pillow talk, (possibly dinner) before going our separate ways. Classic college hook-up and I’m pretty happy with it despite that I haven’t gotten off with him yet. He’s leaving the country in a few months for an internship and I will probably not see him again afterwards. So this relationship-thing has a built-in expiration date.

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