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 thought “Oh man, that’s me.  I like ___ so much, but I don’t want to ruin our friendship,” do something for Captain Awkward.

Just ask ____ out already. On a date.  A real, live date.  A DATE-date, where you make it clear that a date is happening between two people who are on a date.  With each other.

Listen:  Chances are very high that _____ already knows how you feel or at least has picked up on your Firthing.

1. What’s the best thing that could happen?

_____ feels the same way about you and has also been a big coward about saying it before now. DATEMAGIC!

2. What’s another really good thing that could happen?

_____ says “Hey, this really caught me off-guard, can I think about it?” and you say “Sure” and ____ looks at you with new eyes and the air between you becomes charged in a way that it wasn’t before, the two of you keep sneaking looks at each other and blushing and looking away when you catch each other at it and at some point you both know what’s going to happen but you haven’t admitted it to each other or yourselves and then _____ invites you inside one night to “listen to music” and your stomach is filled with nervous butterflies, like “Is this the night?  Is it now?” and it is.

Finger Puppets
Will you go out with us? No? Ok, that's cool.

3. What’s a medium-good thing that could happen?

______ doesn’t feel the same way about you and says so, and it’s an awkward moment pungent with the stink of rejection.  But you say “I understand, and I’m sorry if I made you uncomfortable. I had to give it a shot,” and your friend says “I’m sorry too, because you are really cool and I have thought about it myself more than once. I wish I felt differently,” (and you can’t see it, but I’m acting this scene out with finger-puppets right now) and you back the fuck off and move on and your friendship survives because it is based on mutual respect and shared interests and acceptance and humor.

4.  What’s a not-good, but totally survive-able thing that could happen?

You go on the date and one or both of you figure out that there is no chemistry.  Now you know and have a story you can laugh about later, like, “Remember when we tried dating?  Oh man, that was a terrible idea!

Friendship is extremely durable.  It can handle honesty and courage.  You won’t ruin a real friendship by speaking up.

I don’t want to spend too much time on worst-case scenarios, but this is a Certified Honesty Zone, so here you go:

5. This is a bad thing that could happen: Sometimes you aren’t actually friends.  Sometimes you were never friends.  Sometimes you were the person in the comic, and everything you did had an ulterior motive.  Sometimes your constant attention and unspoken desire made ______ really uncomfortable, and the phrase “let’s be friends” or “sure, we’re friends” means “I don’t know how to reject you and I’m scared to hurt your feelings, so I’m looking for a word you’ll accept.” If this is the case, and you speak up and it goes badly and _____ avoids you for the rest of time, you are not losing a friend.  You are puncturing your own fantasy, which is painful enough that I get why you never spoke up before now.  But do you want to be the person who makes your fantasy of being with someone more important than the real feelings of that actual someone?  You are doing everyone a favor by being truthful about your desires and letting the chips fall.

Let’s review the rules:

  1. The other person is just a human
  2. Do it sooner rather than later, before you get too caught up in a fantasy or invested in the outcome.
  3. Nobody owes you time or affection, so don’t approach dating with a sense of entitlement.
  4. Be cool with rejection. (I cannot overstate the importance of respecting the “no.”  You WILL ruin the friendship, even a real friendship permanently if you say “Go out with me?” and the other person says “Sorry, no thanks” and you hang around like a fart in a car hoping they’ll change their mind.)
  5. You can’t control whether someone will like you.
  6. Listen to the other person – pay attention to the actual interaction that is taking place and not the one in your head.
  7. Don’t date anyone who isn’t as cool as your friends.
  8. New Rule: Acknowledge the awkward. Don’t try to be smooth if you’re not smooth.  Just say “Hey, I feel like a dork but I like you.”

January 28, 2011. You’ve got two days, which is enough time to get your courage up but not enough time to totally overthink it.  I want stories.

24 thoughts on “The Year of Living Awkwardly

  1. I just did this on Monday. I had a situation that was just on the verge of this (the friendship is still really new and could go either way). Didn’t get a date, but I feel SO MUCH BETTER for having had the conversation.

    Also – early is better. I hadn’t had enough time for the attraction to become a full-fledged crush. So the disappointment was less than it would have been a month from now.

  2. But… Rule 7 is so HARD! And that comic has often felt like the story of my life. So many lessons to unlearn and internal dialogues to ignore…

  3. But I won’t be seeing the person I have a crush on til sunday….

    Happy early bday by the way.

      1. Just got back from seeing my crush. He didn’t necessarily say no perse? He’s busy (in a band, and they’ve got shows coming up) but he likes the idea of hanging out. He was all ‘Thanks for wanting to be social with me. That’s very sweet of you.’

        I almost died. >.< ANYWAY. Here's your bday gift (albeit a little late)

    1. Your blog is I didn’t know about it before today! Next step: Join forces, conquer world.

  4. Ha, my situation is very awkward. Honesty zone, right? There’s this guy. We met a couple of times before, but in 2006, we got to know one another, we liked one another, and it quickly became sexual without the relationship (my fault, I had an ex that made me squeamish about relationships). During the first year, we had a “talk” and he told me he didn’t like me “like that” anymore, but we kept the sex. It went on through 2010, even after we graduated college. Then, he went away to the Air Force. I held on the whole time, hoping he’d realize that he was still into me. But with hundreds of miles between us, I’m coming to the realization that we were, and are, good friends, with great sexual chemistry, and great sex, and that’s it. Now, after four years of emotional investment (even though we both dated others throughout college), it’s going to take time to shift my thinking, but I hope I’ll get there. (Though I have to say, I’m looking forward to the next time he visits–I miss that sex!)

    1. Captain Awkward has never done anything like that. Nope, not even once. Not me! Never done that….


      Good for coming clean about what is going on and honoring your own feelings and desires.

    1. Thanks! I need to create a CaptainAwkwarddotcom feed, but until then you can find me at JPeep.

      I also need to pull some stuff together for your guest blog thingy…I need to pull out the tale of the guy who would not break eye contact, ever, not even for a second.

      1. PLEASE GUEST POST THAT WOULD BE AMAAAAAZING! I’d love to plug your blog on my site. I have already told many friends about it.

  5. I had this odd thing happen to me where I was on both sides at the same time.
    I finally decided to ask out this guy even though its practically unheard of for a girl to do so around here. But I’d never felt this way about a guy before and the chemistry was great. He had always been the one to take the initiative to further our friendship in the entire year or so that I’d known him, and all the signs were there.
    I bluntly asked him out. He said he’d thought about it too and for a moment there I thought it was going to be a yes. But then came the dreaded “I like you But..” He led me to believe that he wanted something more long term than I did. I backed off immediately and said that’s fine (pretty honestly).
    Next morning it hit me like a ton of bricks, and it felt like my heart had been ripped out. For a moment I was tempted to say, “Dammit, I’ll do whatever you want, if its simply a matter of wanting a serious relationship”, though I’d only wanted to explore and go with the flow. Funny, I’d promised myself that it wouldn’t matter if he said no. Well, we’re still friends today. He thinks I’m “over it”. He confided in me about his feelings for a classmate, Anita, and I was supportive. Oh, there is always an underlying hope that just Maybe there’s still a chance, but its not more important than everything we’ve shared or what he wants.
    He’s made it pretty hard for me to move on (in a matter of speaking I mean; I’m not playing the blame game). We’ve always had a flirty kind of friendship, and most people think we’re dating anyway. He never contradicts that. He hangs out with me pretty often, we went on a trip, only the 2 of us. The physical comfort (which both of us feel) is still there, and he treats me differently from any other girl, even Anita. He know that she more than reciprocates, yet he hasn’t asked her out. So you can understand that I’m simply back to where I was before I’d asked him out, without any kind of closure. Also several of my friends said I should have pushed the matter and its only my ego that I backed off. I can’t say I agree.
    I can’t stand his friends anyway, though I made an effort to hang out with them. Without a label to our relationship, it simply didn’t work out and I always felt an outsider there. I like to think I’m sensible and I’ve brutally forced myself to move on, besides the occassional internal sigh.
    On the other hand – Around the same time, another friend pursued me ardently, declaring his everlasting love which he could no longer hide. This revelation was a gigantic stunner. Even though I considered him one of my best friends, it was still freaky. And he pushed it so much, our friendship is in tatters now.

    1. That’s a rough situation with your friend, I’m sorry. It’s really hard to puncture the fantasy, especially when you’ve gotten so many conflicting signals from the other person. Good for you for being brave, though.

      I’m really sorry also about the guy who pursued you. The whole point is to ask the other person out when the stakes are low and BEFORE it gets to Obsessive Love territory.

      You didn’t ask for advice, but I am an advice-giver, and your first situation makes my heart hurt. What would happen if you stopped “emotionally dating” your friend for a while? No trips together, no flirtation, no “physical comfort,” no more cataloging all the ways he treats you differently or better than girls he actually likes. You have, in words, how he feels, but you also have all these mixed signals from him, and I can see why it’s hurtful and confusing and hard to let go of hope that one day he’ll look up and really see you the way you want to be seen.

      I swore a blood oath that I would never mention or admit to reading He’s Just Not That Into You (It was my roommate’s copy. It was winter. I was weak.), and I think the book is really patronizing from the title to the horrible pink cover, and I think there are a lot more “it’s complicated” situations, especially where geeks are concerned – we tend to be more fluid about gender roles sometimes and not so committed to the idea that men should be the relentless pursuers – but it might be good FOR YOU to decide, okay, he told exactly how he feels so the best thing I can do for myself is believe him and act as if he’s telling the truth. You don’t have to end the friendship, you don’t have to even have a big conversation about it if you don’t want to. Just live your life and gradually make him a smaller part of it and see what happens. If you pull back and he asks why, you can say “Ever since we had that big awkward conversation, I feel a little weird about being so snuggly. Can we not?”

      I wish you well.

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