
All The Big Mistakes Women Make - Chrissie Mayr | Modern Wisdom Podcast 303
Chrissie Mayr (guest), Chris Williamson (host), Narrator
In this episode of Modern Wisdom, featuring Chrissie Mayr and Chris Williamson, All The Big Mistakes Women Make - Chrissie Mayr | Modern Wisdom Podcast 303 explores modern Dating Mistakes: Chrissie Mayr’s Hard-Won Lessons For Women Chrissie Mayr and Chris Williamson unpack the most common mistakes women make in dating, relationships, and early adulthood, drawing heavily on Chrissie’s personal experiences. They discuss people-pleasing, overvaluing sexual attention, consumerism, and relying on bad cultural advice instead of developing self-knowledge and long-term goals. The conversation contrasts how men and women typically cope with breakups and loneliness, and how agreeable or disagreeable traits can sabotage attraction. They end by emphasizing communication, supportive partners, strong friendships, and aligning your life with what you truly value—ideally much earlier than most people do.
Modern Dating Mistakes: Chrissie Mayr’s Hard-Won Lessons For Women
Chrissie Mayr and Chris Williamson unpack the most common mistakes women make in dating, relationships, and early adulthood, drawing heavily on Chrissie’s personal experiences. They discuss people-pleasing, overvaluing sexual attention, consumerism, and relying on bad cultural advice instead of developing self-knowledge and long-term goals. The conversation contrasts how men and women typically cope with breakups and loneliness, and how agreeable or disagreeable traits can sabotage attraction. They end by emphasizing communication, supportive partners, strong friendships, and aligning your life with what you truly value—ideally much earlier than most people do.
Key Takeaways
Stop over-prioritizing whether he likes you; ask if you like him.
Chrissie realized she spent years worrying if she was hot or good enough instead of asking basic questions like, “Is he reliable? ...
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Excessive agreeableness makes you boring and unknowable to partners.
Always saying “whatever you want” about food, plans, or sex may feel low-maintenance, but it hides your real preferences and robs your partner of the chance to know and grow with you—often leading to boredom and emotional distance.
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Use your 20s to discover real interests, not just consume culture.
Chrissie regrets wasting money and time on mindless shopping and reality TV instead of developing passions and skills; she argues that hobbies and goals are what make you interesting, resilient, and attractive in the long run.
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Be wary of dating advice from media and young “experts.”
Magazines, apps, and viral advice columns often push political or consumerist agendas (“you deserve it all,” “never settle”) that encourage disposal of decent partners and avoidance of hard work, rather than teaching sacrifice and problem-solving.
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Learn to ask directly—for raises, gifts, attention, and support.
Women often expect bosses, partners, or friends to “just know” what they need; Chrissie stresses that in both career and relationships, you must clearly articulate desires and boundaries instead of silently resenting people for not mind-reading.
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Both sexes default to unhealthy coping when single—fight that pull.
Women tend to retreat into brunch, gossip, and rebound sex; men into isolation, resentment, and work-obsession. ...
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Choose partners who treat your dreams like their own.
Chrissie highlights her current boyfriend’s active support—pushing her to voice preferences and backing her career—as the key difference from past relationships; a strong partner should champion your goals, not compete with or diminish them.
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Notable Quotes
“I undervalued communication and I undervalued me liking the guy.”
— Chrissie Mayr
“The girls who’ve been the most agreeable are the ones I’ve got bored of the quickest—because it’s kind of like dating nothing.”
— Chris Williamson
“Hooking up is so fun, but now looking back, I know there’s only really 10 or 12 different kinds of dudes—you don’t need six rounds of each.”
— Chrissie Mayr
“You can’t bring your single life into a relationship. You have to build your novelty and excitement from the ground up with this person.”
— Chrissie Mayr
“No one has enough friends to be a dick to the friends that you have.”
— Chris Williamson
Questions Answered in This Episode
How can women practically transition from people-pleasing to asserting needs without feeling like they’ve become “nagging” or demanding?
Chrissie Mayr and Chris Williamson unpack the most common mistakes women make in dating, relationships, and early adulthood, drawing heavily on Chrissie’s personal experiences. ...
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What concrete criteria should someone use to decide whether a partner truly supports their long-term goals versus just tolerates them?
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How can young adults distinguish between helpful self-improvement advice and the kind of shallow, consumerist messages Chrissie criticizes?
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In what ways can men and women each borrow the other’s healthier coping strategies after breakups to avoid resentment or reckless behavior?
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Given the pressures around fertility, career, and relationships, how early should women start planning for potential motherhood—even if they’re unsure they want kids?
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Transcript Preview
I undervalued communication, and I undervalued me liking the guy. It was always like, (gasps) "Am I good enough? Am I hot enough? Am I competing ac- amongst these other women?" Instead of flipping it to like, "Is this guy good enough? Does he even have a job?" (laughs) You know, he was late.
Chrissie May. Welcome to the show.
Thanks for having me.
Have you managed to get dog poo off your shoe?
(laughs) Yeah. You know, it's starting to be springtime here in New York, and part of that means going around the yard and picking up poops and throwing them over the fence.
(laughs) Why is that only a springtime thing? What happens in winter?
(laughs) Well, what happens in winter is they get covered in the snow, and then th- when the snow melts, like, all the poops appear.
(laughs)
Like, ah. That's kind of what's been happening here in New York. You're like, "Damn, somebody had a busy winter." And then you, like, say it to the dog, and you're like... Yeah.
(laughs) I was walking, I went on a little walk earlier on. This is like a weird thing that people who love dogs but don't have a dog do. So whenever someone that's coming towards me on the street is walking a dog on a leash, I won't make eye contact at all with the other person because this is my 15 seconds of dog attention for, like, potentially for the day, you know, if I have a, a bad walk-
Yeah.
... and I don't pick up many dogs. So I just... But I wonder what they must think of me, 'cause I'm just this psychopath walking past staring at their dog, like longingly staring at their dog, 'cause I love dogs 'cause they're awesome. And, um-
Yeah.
... yeah, I just wonder, I wonder if it weirds people out.
Uh, it actually makes me feel really good to hear that you do exactly what I do. I could not care less about the owner. Like, e- exactly, like I h- I hoard as much dog time as possible. Like, (laughs) I almost think, like, y- you know, like in, when I was in New York City more, like there'd be dog walkers and then you'd be like, "Jackpot." You know, I'd like-
(laughs)
... I will cross a street just to meet a dog. And then like, I'm like what would be like the next level thing that like the dog just couldn't... I think if you just laid down, that would be the thing the dog, like, could not avoid. At that point, it's like the dog is gonna jump on you, 'cause you're just like-
So the human's- the human's just there-
Yeah.
... to facilitate you looking at a dog, basically.
Yeah, and I, and when I walk, actually it's like my, my boyfriend's mom's dog, but I feel like we're like close. Like, I was there the day she came home, so I feel like, I don't know, we're like, we're close buds. If, when people just go up to Muffin, I don't take it as a personal offense. I'm just like, "No, she's super F-in cute," Like, of course.
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