Quotes & Sayings About Awkward Conversations

From day one it was like society was this violent, complicated dance and everybody had taken lessons but me. Knocked to the floor again, climbing to my feet each time, bloody and humiliated. Always met with disapproving faces, waiting for me to leave so I'd stop fucking up the party.
The wanted to push me outside, where the freaks huddled in the cold. Out there with the misfits, the broken, the glazed-eye types who can only watch as the normals enjoy their shiny new cars and careers and marriages and vacations with the kids.
The freaks spend their lives shambling around, wondering how they got left out, mumbling about conspiracy theories and bigfoot sightings. Their encounters with the world are marked by awkward conversations and stifled laughter, hidden smirks and rolled eyes. And worst of all, pity. — David Wong

On this particular afternoon, they all started teasing me. "You should go out to the lobby, Jo. There's a hot guy out there. Go talk to him!" they said.
"No," I said. "Stop it! I'm not doing that."
I was all of twenty-three, and I wasn't exactly outgoing.

She was a bit awkward--no doubt about that.

I hadn't dated all that much, and I'd never had a serious relationship--nothing that lasted longer than a month or two. I'd always been an introvert and still am (believe it or not). I was also very picky, and I just wasn't the type of girl who struck up conversations with guys I didn't know. I was honestly comfortable being single; I didn't think that much of it.
"Who is this guy, anyway?" I asked, since they all seemed to know him for some reason.
"Oh, they call him Hot John," someone said, laughing.
Hot John? There was no way I was going out in that lobby to strike up a conversation with some guy called Hot John. — Joanna Gaines

I'm never really comfortable at parties. Maybe I'm just not the partying type.
... I think it's because I'm never sure what to do with myself.
I mean, there're drinks, but I don't like being drunk ... There's music, but I never really learned to dance to anything that involved an electric guitar. There are people to talk to ... but once you put all the stupid things I do aside, I'm really not that interesting. I like reading, staying home, going on walks with my dog ... Who wants to hear about that? Especially when I would have to scream it over music to which no one dances.
So I'm there but not drinking, listening to music but not dancing, and trying to have conversations with near-strangers about anything other than my own stupid life ... Leads to a lot of awkward pauses. And then I start wondering why I showed up in the first place.
Cold Days (The Dresden Files Book 14), pg. 33 — Jim Butcher

Do you know someone who needs hours alone every day? Who loves quiet conversations about feelings or ideas, and can give a dynamite presentation to a big audience, but seems awkward in groups and maladroit at small talk? Who has to be dragged to parties and then needs the rest of the day to recuperate? Who growls or scowls or grunts or winces when accosted with pleasantries by people who are just trying to be nice?
If so, do you tell this person he is "too serious," or ask if he is okay? Regard him as aloof, arrogant, rude? Redouble your efforts to draw him out?
If you answered yes to these questions, chances are that you have an introvert on your hands - and that you aren't caring for him properly. — Jon Rauch

Don't you ever have conversations where someone took a wrong turn at some point, and then it goes on and on and it becomes too late to put things right? — Nick Hornby

The discovery of Viagra was a similar story. Initially, the drug had been tested as a treatment for chest pain (angina), and for that purpose it was a failure. Then patients started reporting a curious side effect. (Imagine those awkward conversations: "Doc, my chest still hurts ... but, um, I've been noticing an effect somewhere else ... ") — Chip Heath

I had no idea you could be a specialist at awkward conversations — Sophie Kinsella

We don't live in a shared reality, we each live in a reality of our own, and causing upset is often the price of trying to reach each other. It's always easier to dismiss other people than to go through the awkward and time consuming process of understanding them. We have given 'taking offense' a social status it doesn't deserve: it's not much more than a way of avoiding difficult conversations. — Frankie Boyle

It's even more awkward when we're face to face with people. It used to be exciting to make plans with friends because you could sit and catch up and talk about what's been going on in your lives. Now when you see someone there's nothing left to say. You've already seen the pictures from their trip to Rio on Facebook. You've read their tweets about the latest diet they're on. And they already texted you about the pregnancy scare. So you end up just sitting and staring at each other until you both start texting other people. — Ellen DeGeneres

I'm all for awkward, frank, sometimes painful conversations about things that give everyone a better perspective on who they are in the here and now, and how they want to proceed from there. — Tunde Adebimpe

Introductions are always weird for me because my name is Hari and it's constantly mispronounced . 'Hurry', 'Hairy' - there are different ways to screw it up, and it leads to these awkward conversations. — Hari Kondabolu

Ricky asks her, "You lost your earrings in the living room?" She shakes her head. "No, I lost them in the bedroom. But the light out here is much better." And there it is. Most leaders prefer to look for answers where the light is better, where they are more comfortable. And the light is certainly better in the measurable, objective, and data-driven world of organizational intelligence (the smart side of the equation) than it is in the messier, more unpredictable world of organizational health. Studying spreadsheets and Gantt charts and financial statements is relatively safe and predictable, which most executives prefer. That's how they've been trained, and that's where they're comfortable. What they usually want to avoid at all costs are subjective conversations that can easily become emotional and awkward. And organizational health is certainly fraught with the potential for subjective and awkward conversations. — Patrick Lencioni

Here I'd thought that the end of the world might have meant I got to stop having incredibly awkward conversations. — Domashita Romero

I find the dead easier to be around than the dying. They are not in pain, not afraid of death. There are no awkward silences and conversations that dance around the obvious. They aren't scary...Cadavers, once you get used to them--and you do that quite fast--are surprisingly easy to be around. — Mary Roach

I'm a bad dater. I'm the most socially awkward person, like carrying on conversations and stuff. — Lauren Conrad

They said words they did not mean, and their conversations seemed to follow all kinds of rules - rules that no one has ever explained to Oscar. — Anne Ursu

I like working with people I know. It saves a lot of awkward conversations and getting-to-know-you kinda moments. You trust the people if you know them. — John C. Reilly

Awkward conversations. They're the heart of the drug trade. The driving force that keeps criminals out of jail is paranoia. You can think you know people, but the truth is, you never know who they're talking to. The life of an outlaw: Around every corner lies a cop. In every basement waits a bust. Every friend is the guy who sells you out to keep his own ass out of jail. Sure, it was rare, but you just never knew.
The result was a series of shorthand and euphemisms so obscure even the pros often weren't sure what they were talking about. Sales became pickups. Pot, ganja, bud, or weed became lettuce, green, happy, herb, smoke... the list went on, and changed from dealer to dealer. — Daniel Younger

I can't talk about my childhood at all, because cannot say "I" when I mean "we," and if I say "we" it leads to a conversation about how I have a dead sister, instead of what I want to talk about. I found that out in the summer. So I don't talk about it. — Jo Walton