Taking Our Power Back In The Dating Game

Podcast Summary

Let's Be Honest with Kristin Cavallari

Episode: Taking Our Power Back In The Dating Game
Date: December 9, 2025
Host: Kristin Cavallari
Platform: Dear Media

Episode Overview

In this episode, Kristin Cavallari dives into real talk about navigating the modern dating world, sharing unfiltered advice and answering listener-submitted dating scenarios. She explores self-worth, emotional availability, communication, red flags, attraction, and empowering yourself while single, all through her signature blend of honesty, humor, and a bit of tough love. Kristin’s guiding theme: taking ownership, knowing your worth, and unapologetically raising your standards.

Key Discussion Points & Insights

1. Men Who Say They Want Commitment, Then Only Want Sex

Kristin’s Take: “Men will and say and do anything to get in your pants. Let’s just establish that, ladies.” (03:49)
- Men may think they want a relationship but realize after a few dates they don’t see a future with you—so they pivot to a physical-only connection.
- “I always resort back to the fact that you will know if he likes you and wants to have a future with you. Men make it very apparent. If you're confused, it's because he does not like you. I'm sorry if this is harsh.” (06:51)

2. He’s Interested But Goes Days Without Reaching Out

If he makes regular plans to see you, don’t overthink a lack of daily texts—especially in early stages or if both are busy.
"I have gotten to a place where...I like it now." (07:49) / "I can't talk to someone all day...I’ve gotten to a really secure place..." (08:12)
Communication gaps may trigger old wounds, but healing and self-security change the game.
In serious relationships, a week without contact is unusual—but early on, space can be normal.

3. Hot and Cold Pursuit

This is similar to the commitment-to-sex switch.
View those who lose interest as helping you get closer to your real person:
- “If someone goes cold, fine, that's not your person, and you don't want to be with someone who doesn't feel the same way about you.” (10:14)
- Reference to “20 dates to your person” idea—see every ending as progress.

4. Dating Someone Great But Lacking Attraction

“Attraction is huge... I think attraction is more than half. And attraction is the hardest piece of the puzzle.” (13:09)
Don’t force a connection if it isn’t there. Sometimes it’s okay—and necessary—to be alone for a while. Use that time for self-work.
“You can't fake attraction. You can't force that.” (14:27)

5. Is It Okay to Date Two People At Once?

Only if you’re honest. “No, you can't lie. Is it okay to date two people at once? Yes. Is it okay to lie about it? No.” (20:24)
Owning up to dishonesty is better than continuing the lie—expect the other person may walk away.

6. Preferring Younger Guys, But None Want to Commit

“Whatever we attract into our lives is because it's whatever we're putting out subconsciously.” (22:21)
Time to dig into why you’re attracted to emotionally unavailable men—patterns often start with you.
Suggestion: do inner work and examine your own fears of intimacy.

7. Blatant Disrespect From Partner’s Children

On being told “deal with it” by your partner: “Wow, what a fucker. This is so unacceptable and not okay. It’s not even funny.” (23:53)
Self-worth comes into play; don’t accept poor treatment. “The bar is pretty low if I'm being completely honest.” (25:01)

8. Major Red Flag: Weird Sexy Pics Before First Date

“Ladies, we are not going on dates with men who send their fucking underwear picture before a first date. No, that's not happening.” (27:31)
Only entertain this if you only want sex; otherwise, recognize it as a misogynistic, douchebag move.

9. Getting “The Ick” & Enjoying Single Life

“Getting the ick quickly is not a bad thing... we've got high standards. The bar’s up here now.” (28:11)
Stay single until you feel inspired to leave singlehood for someone worthy. “When the right man comes, it's going to be effortless.” (28:45)

10. Seven-Year Relationship, Baby, No Proposal—Ultimatum?

“No, you never give an ultimatum... We want men who are so in love with us, so obsessed with us, would do anything for us.” (29:36)
Don’t be afraid to walk away; endings create space for growth and better matches.

11. Single Moms and Dating

“Men do not care if you have kids. I can promise you, promise, promise, promise you.” (31:57)
Any man who balks is “a little boy, not a man.”

12. Developing a Crush on a Friend

Gradual strategy: amp up subtle flirting (touch, proximity) and see how he responds.
After a few times, try a playful mention: “Have you ever thought about us dating?” or share a dream story. (36:28)
“If a relationship can start from a friend dynamic, I think that is good gold.” (37:10)

13. Where to Meet Single Men (35-45) Beyond the Apps

Be social—try new places, classes, bars, or events, especially golf/tennis.
Put more intent into appearance and openness.
“I always will resort back to the fact that when it's supposed to happen, it will.” (39:40)

14. Attracting Emotionally Unavailable Men

“If there's some sort of trauma there, there's something going on from your childhood...” (41:11)
Kristin shares her own past patterns; she sees a real shift once you’ve done the work.

15. When to Sleep With Him

“I don't think it actually matters when you sleep with a guy. Fucking sue me. It doesn't.” (42:51)
Real chemistry transcends timing; if he truly likes you, when you sleep together won’t matter.
But if you tend to regret sex early, wait a month to see his intentions.

16. Situationships & Empowerment

If it suits your needs, go for it—just be clear about your own emotional boundaries.
Women should feel empowered to define the relationship status.

17. Self-Improvement Shrinking the Dating Pool

“It is really hard to find someone...who can see eye to eye with you, but they’re out there...you will attract it.” (46:15)
Don’t settle; your match will be worth the wait.

18. Trust Issues with Male Compliments

Acknowledge your own trust issues—may stem from past relationships or childhood.
Not every compliment is manipulation; sometimes the compliment is real and he wants to sleep with you. Both can be true.

19. Not Excited to Hear from Him After Dates

“That should not be mistaken with chemistry and attraction... that in-between is actually how we know.” (49:17)
How you feel after the date or between dates is the biggest indicator.

Notable Quotes & Memorable Moments

On men’s intentions:
“Men, their goal is to get in your pants. They have two brains, a big one and a little one. And unfortunately, the little one, I think, leads the way sometimes...” (03:35)
On relationship timelines:
“If you knew… that after 20 people, 20 dates, you are going to meet your person… then you would just be moving through these people. Perfect, onto the next.” (09:52)
On self-worth:
“Everything comes back to self-worth. You guys, what we allow depends on how much we respect and love ourselves.” (25:01)
On being single:
“I love myself too much and I value my peace and I love my home and I love my own company that I would never settle for just anybody.” (28:59)
On setting high standards:
“The pool has now become so small because we’re so healed...when you do find someone, they're going to be amazing.” (46:15)

Timestamps of Main Segments

00:22 – 03:30: Kristin sets up the theme and vibe: dating is like cocktails with girlfriends
03:30 – 07:10: Men who want commitment and then pivot to just sex
07:11 – 09:50: How often should he contact you—texting frequency and healthy independence
09:51 – 13:04: Confusion over hot/cold guys and putting “failed” dating in perspective
13:05 – 15:46: Attraction issues—don’t force it if it’s not there
20:11 – 21:57: Is it okay to date two people if you’ve lied about it?
22:10 – 23:49: Middle-aged mom dating younger men; commitment patterns
23:50 – 25:45: Partner’s teenage daughters are rude; toxicity, boundaries, and self-respect
25:46 – 27:42: “Boxer brief” first date guy—major dating red flags
27:43 – 29:35: Getting “the ick” and being happy single
29:36 – 31:48: Ultimatums: to give or not to give in long relationships
31:49 – 32:47: Single moms and dating—the right man doesn’t care about your kids
35:58 – 37:41: Crush on a friend—how to approach & test the waters
38:52 – 41:10: Where to meet men IRL, getting social
42:43 – 44:36: When to sleep with a guy—should you wait?
46:15 – 49:04: Self-improvement and the shrinking dating pool—don’t lower your standards
49:07 – 51:13: Not sure you’re excited to hear from him? Trust your feelings

Tone & Style

Kristin is candid, chatty, and direct, mixing humor, tough love, and empathy. She regularly returns to the importance of self-worth and encourages using singlehood as a time for self-growth, not just as waiting for “the one.” The language is informal, sometimes explicit, and always honest.

Final Takeaway

Kristin’s central message is about “taking your power back” in dating: own your choices, don’t settle, set high standards, do the self-work, and trust that love comes from a place of self-contentment, not desperation.

For more advice, follow Kristin’s podcast for upcoming guest episodes and dating deep-dives.

Podcast Summary

Let's Be Honest with Kristin Cavallari

Episode: Taking Our Power Back In The Dating Game
Date: December 9, 2025
Host: Kristin Cavallari
Platform: Dear Media

Episode Overview

Key Discussion Points & Insights

1. Men Who Say They Want Commitment, Then Only Want Sex

Kristin’s Take: “Men will and say and do anything to get in your pants. Let’s just establish that, ladies.” (03:49)
- Men may think they want a relationship but realize after a few dates they don’t see a future with you—so they pivot to a physical-only connection.
- “I always resort back to the fact that you will know if he likes you and wants to have a future with you. Men make it very apparent. If you're confused, it's because he does not like you. I'm sorry if this is harsh.” (06:51)

2. He’s Interested But Goes Days Without Reaching Out

If he makes regular plans to see you, don’t overthink a lack of daily texts—especially in early stages or if both are busy.
"I have gotten to a place where...I like it now." (07:49) / "I can't talk to someone all day...I’ve gotten to a really secure place..." (08:12)
Communication gaps may trigger old wounds, but healing and self-security change the game.
In serious relationships, a week without contact is unusual—but early on, space can be normal.

3. Hot and Cold Pursuit

This is similar to the commitment-to-sex switch.
View those who lose interest as helping you get closer to your real person:
- “If someone goes cold, fine, that's not your person, and you don't want to be with someone who doesn't feel the same way about you.” (10:14)
- Reference to “20 dates to your person” idea—see every ending as progress.

4. Dating Someone Great But Lacking Attraction

“Attraction is huge... I think attraction is more than half. And attraction is the hardest piece of the puzzle.” (13:09)
Don’t force a connection if it isn’t there. Sometimes it’s okay—and necessary—to be alone for a while. Use that time for self-work.
“You can't fake attraction. You can't force that.” (14:27)

5. Is It Okay to Date Two People At Once?

Only if you’re honest. “No, you can't lie. Is it okay to date two people at once? Yes. Is it okay to lie about it? No.” (20:24)
Owning up to dishonesty is better than continuing the lie—expect the other person may walk away.

6. Preferring Younger Guys, But None Want to Commit

“Whatever we attract into our lives is because it's whatever we're putting out subconsciously.” (22:21)
Time to dig into why you’re attracted to emotionally unavailable men—patterns often start with you.
Suggestion: do inner work and examine your own fears of intimacy.

7. Blatant Disrespect From Partner’s Children

On being told “deal with it” by your partner: “Wow, what a fucker. This is so unacceptable and not okay. It’s not even funny.” (23:53)
Self-worth comes into play; don’t accept poor treatment. “The bar is pretty low if I'm being completely honest.” (25:01)

8. Major Red Flag: Weird Sexy Pics Before First Date

“Ladies, we are not going on dates with men who send their fucking underwear picture before a first date. No, that's not happening.” (27:31)
Only entertain this if you only want sex; otherwise, recognize it as a misogynistic, douchebag move.

9. Getting “The Ick” & Enjoying Single Life

“Getting the ick quickly is not a bad thing... we've got high standards. The bar’s up here now.” (28:11)
Stay single until you feel inspired to leave singlehood for someone worthy. “When the right man comes, it's going to be effortless.” (28:45)

10. Seven-Year Relationship, Baby, No Proposal—Ultimatum?

“No, you never give an ultimatum... We want men who are so in love with us, so obsessed with us, would do anything for us.” (29:36)
Don’t be afraid to walk away; endings create space for growth and better matches.

11. Single Moms and Dating

“Men do not care if you have kids. I can promise you, promise, promise, promise you.” (31:57)
Any man who balks is “a little boy, not a man.”

12. Developing a Crush on a Friend

Gradual strategy: amp up subtle flirting (touch, proximity) and see how he responds.
After a few times, try a playful mention: “Have you ever thought about us dating?” or share a dream story. (36:28)
“If a relationship can start from a friend dynamic, I think that is good gold.” (37:10)

13. Where to Meet Single Men (35-45) Beyond the Apps

Be social—try new places, classes, bars, or events, especially golf/tennis.
Put more intent into appearance and openness.
“I always will resort back to the fact that when it's supposed to happen, it will.” (39:40)

14. Attracting Emotionally Unavailable Men

“If there's some sort of trauma there, there's something going on from your childhood...” (41:11)
Kristin shares her own past patterns; she sees a real shift once you’ve done the work.

15. When to Sleep With Him

“I don't think it actually matters when you sleep with a guy. Fucking sue me. It doesn't.” (42:51)
Real chemistry transcends timing; if he truly likes you, when you sleep together won’t matter.
But if you tend to regret sex early, wait a month to see his intentions.

16. Situationships & Empowerment

If it suits your needs, go for it—just be clear about your own emotional boundaries.
Women should feel empowered to define the relationship status.

17. Self-Improvement Shrinking the Dating Pool

“It is really hard to find someone...who can see eye to eye with you, but they’re out there...you will attract it.” (46:15)
Don’t settle; your match will be worth the wait.

18. Trust Issues with Male Compliments

Acknowledge your own trust issues—may stem from past relationships or childhood.
Not every compliment is manipulation; sometimes the compliment is real and he wants to sleep with you. Both can be true.

19. Not Excited to Hear from Him After Dates

“That should not be mistaken with chemistry and attraction... that in-between is actually how we know.” (49:17)
How you feel after the date or between dates is the biggest indicator.

Notable Quotes & Memorable Moments

On men’s intentions:
“Men, their goal is to get in your pants. They have two brains, a big one and a little one. And unfortunately, the little one, I think, leads the way sometimes...” (03:35)
On relationship timelines:
“If you knew… that after 20 people, 20 dates, you are going to meet your person… then you would just be moving through these people. Perfect, onto the next.” (09:52)
On self-worth:
“Everything comes back to self-worth. You guys, what we allow depends on how much we respect and love ourselves.” (25:01)
On being single:
“I love myself too much and I value my peace and I love my home and I love my own company that I would never settle for just anybody.” (28:59)
On setting high standards:
“The pool has now become so small because we’re so healed...when you do find someone, they're going to be amazing.” (46:15)

Timestamps of Main Segments

00:22 – 03:30: Kristin sets up the theme and vibe: dating is like cocktails with girlfriends
03:30 – 07:10: Men who want commitment and then pivot to just sex
07:11 – 09:50: How often should he contact you—texting frequency and healthy independence
09:51 – 13:04: Confusion over hot/cold guys and putting “failed” dating in perspective
13:05 – 15:46: Attraction issues—don’t force it if it’s not there
20:11 – 21:57: Is it okay to date two people if you’ve lied about it?
22:10 – 23:49: Middle-aged mom dating younger men; commitment patterns
23:50 – 25:45: Partner’s teenage daughters are rude; toxicity, boundaries, and self-respect
25:46 – 27:42: “Boxer brief” first date guy—major dating red flags
27:43 – 29:35: Getting “the ick” and being happy single
29:36 – 31:48: Ultimatums: to give or not to give in long relationships
31:49 – 32:47: Single moms and dating—the right man doesn’t care about your kids
35:58 – 37:41: Crush on a friend—how to approach & test the waters
38:52 – 41:10: Where to meet men IRL, getting social
42:43 – 44:36: When to sleep with a guy—should you wait?
46:15 – 49:04: Self-improvement and the shrinking dating pool—don’t lower your standards
49:07 – 51:13: Not sure you’re excited to hear from him? Trust your feelings

Tone & Style

Final Takeaway

For more advice, follow Kristin’s podcast for upcoming guest episodes and dating deep-dives.

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Summary

Podcast Summary

Let's Be Honest with Kristin Cavallari

Episode Overview

Key Discussion Points & Insights

1. Men Who Say They Want Commitment, Then Only Want Sex

2. He’s Interested But Goes Days Without Reaching Out

3. Hot and Cold Pursuit

4. Dating Someone Great But Lacking Attraction

5. Is It Okay to Date Two People At Once?

6. Preferring Younger Guys, But None Want to Commit

7. Blatant Disrespect From Partner’s Children

8. Major Red Flag: Weird Sexy Pics Before First Date

9. Getting “The Ick” & Enjoying Single Life

10. Seven-Year Relationship, Baby, No Proposal—Ultimatum?

11. Single Moms and Dating

12. Developing a Crush on a Friend

13. Where to Meet Single Men (35-45) Beyond the Apps

14. Attracting Emotionally Unavailable Men

15. When to Sleep With Him

16. Situationships & Empowerment

17. Self-Improvement Shrinking the Dating Pool

18. Trust Issues with Male Compliments

19. Not Excited to Hear from Him After Dates

Notable Quotes & Memorable Moments

Timestamps of Main Segments

Tone & Style

Final Takeaway

Summary

Podcast Summary

Let's Be Honest with Kristin Cavallari

Episode Overview

Key Discussion Points & Insights

1. Men Who Say They Want Commitment, Then Only Want Sex

2. He’s Interested But Goes Days Without Reaching Out

3. Hot and Cold Pursuit

4. Dating Someone Great But Lacking Attraction

5. Is It Okay to Date Two People At Once?

6. Preferring Younger Guys, But None Want to Commit

7. Blatant Disrespect From Partner’s Children

8. Major Red Flag: Weird Sexy Pics Before First Date

9. Getting “The Ick” & Enjoying Single Life

10. Seven-Year Relationship, Baby, No Proposal—Ultimatum?

11. Single Moms and Dating

12. Developing a Crush on a Friend

13. Where to Meet Single Men (35-45) Beyond the Apps

14. Attracting Emotionally Unavailable Men

15. When to Sleep With Him

16. Situationships & Empowerment

17. Self-Improvement Shrinking the Dating Pool

18. Trust Issues with Male Compliments

19. Not Excited to Hear from Him After Dates

Notable Quotes & Memorable Moments

Timestamps of Main Segments

Tone & Style

Final Takeaway