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I met the CMO of an extremely controversial hospitality management group and wellness empire at a nightclub they own last night and asked him soooo many questions. I’m morbidly fascinated by the inner workings of the brand, its many contradictions, and the Dave Portnoy-esque cult of personality surrounding its infamous founder—but I also wanted to understand the mindset of someone who’d choose to work for him at such a high level.
I was really feeling my journalism oats and he told me I’m a very smart woman which duh but okay thanks bro. Don’t be afraid to ask questions of people you’ve just met; it can lead to some interesting conversations!
I was really feeling my journalism oats and he told me I’m a very smart woman which duh but okay thanks bro. Don’t be afraid to ask questions of people you’ve just met; it can lead to some interesting conversations!
Jul 12, 2025
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bonus points if they get the reference!
extra bonus points if they don’t because then i get to dive into the full lore of this interview and my complicated feelings about azealia banks, which always makes for a fun conversation starter. i usually follow up by asking if they have a problematic fave because who doesn’t?
i’ve found you really can’t go wrong talking about things that are deeply personal like music, movies, TV, or anything tied to culture. They’re all great entry points! yes, the key is to be genuinely interested—ask questions— but also give something back (because let’s face it, sometimes you’re the one making it awkward). I think awkwardness usually comes down to trying to find a balance of reciprocity. is someone talking way too much or way too little? learn to know when the conversation is worth sticking around for and when it’s time to excercise some of that beautiful free will we all have and bounce ✌🏽.
extra bonus points if they don’t because then i get to dive into the full lore of this interview and my complicated feelings about azealia banks, which always makes for a fun conversation starter. i usually follow up by asking if they have a problematic fave because who doesn’t?
i’ve found you really can’t go wrong talking about things that are deeply personal like music, movies, TV, or anything tied to culture. They’re all great entry points! yes, the key is to be genuinely interested—ask questions— but also give something back (because let’s face it, sometimes you’re the one making it awkward). I think awkwardness usually comes down to trying to find a balance of reciprocity. is someone talking way too much or way too little? learn to know when the conversation is worth sticking around for and when it’s time to excercise some of that beautiful free will we all have and bounce ✌🏽.
May 21, 2025
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💖i try really hard to ask interesting questions — mainly because I hate small talk but also because a great question opens many doors and rabbit holes. a great question can catch people off guard, make them think and helps you learn so much about who they are and what they value. so when people say this to me, I won’t lie it feels great
Jan 3, 2025
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I love to ask what people are currently “in to” - meaning current inspirations, fixations, interests, etc.
1. It’s subtle but revealing- I now know what you are interested in and get a hint at how you view life (ex. some interests can be perceived as narcissistic/surface level vs. thoughtful/curious) *Granted, not eveyone will have a good answer (or may not even be able to answer) and that will tell you all you need to know!!
2. Naturally we love to talk about ourselves and our passions so it will certainly keep the conversation going. Extra points for asking questions about what they say (maybe you’re interested, maybe you’re not- but at least it’s not awkward anymore)
1. It’s subtle but revealing- I now know what you are interested in and get a hint at how you view life (ex. some interests can be perceived as narcissistic/surface level vs. thoughtful/curious) *Granted, not eveyone will have a good answer (or may not even be able to answer) and that will tell you all you need to know!!
2. Naturally we love to talk about ourselves and our passions so it will certainly keep the conversation going. Extra points for asking questions about what they say (maybe you’re interested, maybe you’re not- but at least it’s not awkward anymore)
May 22, 2025
Top Recs from @taterhole
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It lends a reflective and wistful tone to written communications imo…
Jul 10, 2025
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My dad teases me about how when I was a little kid, my favorite thing to do when I was on the landline phone with somebody—be it a relative or one of my best friends—was to breathlessly describe the things that were in my bedroom so that they could have a mental picture of everything I loved and chose to surround myself with, and where I sat at that moment in time. Perfectly Imperfect reminds me of that so thanks for always listening and for sharing with me too 💌
Feb 23, 2025
May 28, 2025