Can we all share awkward stories? Like a WordPress sleepover with strangers, no smores and no ghost stories.

Last night, I was playing Monopoly Deal with some of my friends (I’m cool) and we got on the subject of people we know that are dead. Naturally, I brought up how awkward it is when you meet someone new and you have a Facebook friend in common who is dead. It’s like, do I bring it up? do we ignore it? or do we admit that it’s kinda funny that the one friend we have common is a dead dude? We lolled at how awkward it is, but like 2 AM sleepy this-is-the-funniest-thing-ever-lolled.

My friend came to my improv show today and when it was over, I pointed at this guy in my improv class and was like, “Hey, he knows our dead friend.”

We go up to him, kind of lolling, and I yell “Hey, you know our dead friend!” Worst. conversation. starter. ever.

My classmate was super weirded out and a 45-second conversation ensued. Β To make things worse (read:better), my classmate’s friend had lipstick on her teeth, but we decided not to tell her because it was already the most awkward conversation ever.

I am clearly super good at making new friends/being awkward when it counts.


33 thoughts on “Awkward

  1. barkinginthedark says:

    AJ.,Funny idea…there might be a couple of winners. Coincidently, I’m at this moment writing a true story of my first teen-age date (15 yrs old) with a girl I was crazy for… it is awkward times 10. will post it sometime soon…continue

  2. La Stranezza says:

    I’m not allowed to play Monopoly anymore…Apparently, it makes me really angry. Also, for the longest time, I was incapable of playing Risk. I blame my grandfather for that one.

  3. Michael Sadowski says:

    Ms. Ashley,
    I died for seventeen minutes on April 5, 2002. Ask me about it sometime. I’ll tell you the story…but I have to charge you a fee as this one’s too good to pass around free. True story.

  4. joem18b says:

    I decided to try mentioning a dead friend to others and you’re right. It was awkward. My friend John died, so I spoke to a number of folks about him, like, did you know our friend John died? And every one of them was like, John was a real asshole, dude, I’m glad he’s gone. So at first, no LOL for me, But then I got to thinking that maybe he was a real asshole after all and then it was LOL for me too.

  5. Rachael Black says:

    oh how I wish I was able to see your stand-up. There’s no way I wouldn’t have fucking laughed my ass off with a good friend over the dead friend thing.Black humor is the only humor -wicked smile-.
    Lost count of awkward moments sometime before graduating college…. In 1982.

    Okay here’s one: About 20 years ago Lucky Ex-Husband Number One and I had a weekly dinner party with another couple. We’d play board games (the night preceding awkward moment was Jenga and Clue) and whoever hosted made the meal. So we all had too much wine with dinner one evening
    The next day we ran into our friends in town, both of them utterly hung over.
    I said “Hell, good thing we all gave it a rest after that Clue game and didn’t go on to Trivial Pursuit!”
    Everyone turned to me with a look of ‘whaaaaaat?’ and was dead silent until my then hubby announced ‘Rachael we DID play Trivial Pursuit. You won.’
    Ummmm apparently I did. In a total black-out.

    Ta Da! I got a million of em -shudders-

  6. improvmantra says:

    So I run into this guy I kinda know at a bar, he’s white and an actor. He’s with this stunning African American woman. I knew him because I had taugh one of his daughters in school. The daughter had the flawless mocha colored skin, that us pasty, blochy-skinned, Northern European types would love to have. So I say to this woman, “Oh, hey, I saw your daughter the other day.”
    Woman, “Oh? Where?”
    Me, “Around town, with Joe.” (the dad)
    Woman, “How do you know she’s my daughter?”
    Me, (chuckling) “Well….”
    Woman, “…..” Stare.
    Me (small voice), “She was… ya know…with Joe…”
    Woman (with look of scorn), “Ah. Just because she’s black doesn’t mean she’s my daughter.”
    Joe (laughing nerviously), “Yeah. That’s not her daughter. She’s my first wife’s.”

    I couldn’t really talk too much after that, I had my foot wedged in my teeth.
    Subtle racism and mentioning the first wife all at once! I am awesome!

  7. Urethra Franklin says:

    I used to go out to Palm Springs for the weekend with a few women I worked with at a previous job. I went to lunch with two of them one day and they brought along a woman from the Marketing department who they’d invited to join us on the next getaway. I didn’t know her well but she sent my gaydar into the red zone the few times I’d been in meetings with her.

    We were discussing the best dates for our next trip and the first weekend we were all free was around the time of the Dinah Shore Golf Tournament when billions of lesbians from all over the globe flock to Palm Springs and every available hotel and motel room is booked months in advance. I said I thought the event might be during that weekend then turned to the Marketing Lady and asked, “Do you know when Dinah is? I haven’t been in years but isn’t it always in early April?”

    She looked at me strangely and said, “I have no idea. How would I know?”

    I’d thought that since the other women in the group (and everyone else at work for that matter) knew I was gay that they knew Marketing Lady was too. I wasn’t sure if she wasn’t out just to them or wasn’t out at all and I felt really bad. I said something about thinking I’d heard her say she used to live out in the desert and tried to change the subject.

    We finished eating and the other two women went to make a restroom stop before heading back to work. Once they were gone I turned to Marketing Lady and said, “I’m so sorry. I shouldn’t have assumed just because they all know about me. I won’t say anything, but they’re all totally cool and no one cares. You can tell them.”

    Marketing Lady (giving me that look again): Tell them what?

    Me: That you’re gay.

    Marketing Lady: What? I’m not gay.

    Me: Umm … oh. Sorry.

    My friends thought the whole thing was hysterical when I told them and confessed they’d brought her to lunch with the intention of asking me later if she was gay or not. They’d thought she was too and wanted to get my “expert” opinion.

    I don’t know which is worse: gaydar fail or pregnancy vs. fat detection fail …

  8. lorrelee1970 says:

    Dead friends on Facebook posting on their own wall and yours is what is creepy. Don’t give anyone access to your account when you are alive. They will just muck it up when you are dead. I’ve seen it happen.

  9. thewaiting says:

    When I was in seventh grade, my mom always packed a lunch for me at school.

    And one day, when I opened my lunch and removed the piece of aluminum foil that was wrapped around my soda, I learned that she had accidentally packed me a Miller Lite to drink.

    Pretty awkward.

  10. bestbathroombooks says:

    At a party two years running with two friends. Everyone is lit.
    Year one
    Joe: How are your twin babies?
    Danny: My wife lost the babies.
    Next year. Everyone is lit again.
    Joe: Hey, Danny. How are the twins?
    Danny: They’re still dead.
    Yep. True. Not as awkward when everyone’s drunk.

  11. Dalai Lina says:

    I was invited to a luncheon at a club – the same club that I had just heard a story about. Apparently a young girl was caught messing around with a couple boys in the locker room shower. Scandalous.

    So I turn to the new woman I was getting acquainted with and said,

    “Can you believe those kids getting caught messing around in the bathroom!”

    “Yes, that was my daughter.”


    I still run into her occasionally around town and want to RUN and HIDE.

  12. Anxiety Girl says:

    I was in Grass Valley, CA visiting my dad, he took me to a cafe. Something weird about small towns, apparently the waitresses can wear whatever they want and don’t have to have a uniform of any sort, nor modest clothing. So our young waitress (guessing about 19-21) is wearing a midriff shirt and she had a HUGE belly, the thing is she was thin everywhere else. So naturally I just assumed she was one of those chic “cool” I’m going to show off my baby belly types, so I asked, “When are you due?” To which she gave me a funny look and replied, “Um I’m not.” I turned bright red and apologized and she said, “it’s okay I get it all the time.” So I’m not sure which moment was more awkward, the fact that I called her now obviously fat/beer belly pregnant OR the fact that she gets it all the time and still wears shirts that only a pregnant celebrity could pull off wearing. The best part was we went to a street fair a couple days later and there she was, belly and all.

  13. Jacob Spire says:

    I once had an awkward silence during a date.
    I thought it would be funny to go, “Hey! Awkward silence!” (not to mention that the silence would be broken), and so I said those words.

    Not only did the awkward silence continue, but it became now mingled in an awkward conversation.

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