Anastacia Milani and Jennifer Marie

Cali On The Rocks Podcast

Society EN ↓ 19 episodes

Shit gets rocky, but we sip anyway. đŸ„‚Welcome to Cali on the Rocks with ya girls Anastacia Milani & Jennifer Marie— where millennial women unpack friendships, relationships, sex, family, and all the hot topics in between
 one drink at a time. The conversations might get rocky, but that’s exactly how we like them. Episodes every Friday!**if you’re in a rocky situation email us and tell us about it! Make sure to put your name, age & how long you been in this situation. Email to: CaliOnTheRocksPod@gmail.com***Stay Connected with us:IG: @CaliOnTheRocksPodTikTok: @CaliOnTheRocksPodYouTube: @CaliOnT...

Author

Anastacia Milani and Jennifer Marie

Category

Society

Podcast website

podcasters.spotify.com

Latest episode

Jul 10, 2026

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Episodes

Nineteenth Sip/Episode: Is It Easier to Find A Good Man or a Good Woman? | Boss Women + BET Awards 10.07.2026

This week on Cali on the Rocks, we’re back sipping on our favorite Cutwater (at this point
 where’s our sponsorship? đŸ€ŁđŸž). We kick things off by recapping our week and talking about the BET Awards, including some of our favorite looks from the night. Then we dive into our first topic: the era of the “Boss Woman.” Are women really leveling up and taking over, or has the term taken on a whole new m...

Eighteenth Sip/Episode: Is It A Flex To Be 30+ With No Kids? | Simps & Tricking | Friendship Loyalty 03.07.2026

This week on Cali on the Rocks, we’re back with our go-to Cutwater Long Island Iced Tea 🍾 because at this point
 it’s part of the family. 😂 We waste no time jumping into our first topic: what happens when one of your friends stops being friends with someone in the group? Are you expected to cut that person off too, or can you stay neutral and maintain your own friendships? 👀 In our Take 10, we...

Seventeenth Sip/Episode: Stop Being A HATERRRRR đŸ€ŁđŸ‘ | Birthday Bellini’s & Juneteenth Recap | 26.06.2026

Happy Birthday to our girl Anastacia!! đŸ„łđŸŽ‰ This week on Cali on the Rocks, we’re celebrating our amazing co-host’s birthday the only way we know how
 with a delicious Peach Bellini! đŸ‘đŸ„‚ Made with Bacardi Rum, Prosecco, Peach Schnapps, blended peaches, and topped off with Sangria
 trust us, this one is definitely worth trying! After catching up on our week, we jump right into Take 10, where we br...

Sixteenth Sip/Episode: The Sexiest Thing A Man Can Offer | Something Strange For A Little Piece Of $ 19.06.2026

This week on Cali on the Rocks, we’re back with another Cutwater Espresso Martini ☕🍾 and at this point, these things officially have us in a chokehold because they completely remove our filter. 😭 We kick things off by catching up on our week and sharing what we’ve got planned in the upcoming weeks before diving right into our first topic: Is the sexiest thing a man can do
 remove stress from a...

Fifteenth Sip/Episode: Should Your Man Control How You Dress? 👀 | Falling For Potential 12.06.2026

This week on Cali on the Rocks, we’re back with another Cutwater Long Island Iced Tea 🍾 because y’all already know how we get down. We kick things off by catching up on our week. Thankfully, nothing too rocky has been going on, but the girls have definitely been spending some time catching up on their favorite shows. Then we get into our first topic: would you change the way you dress if your man...

Fourteenth Sip/Episode: Jenn’s Houston Trip Recap + Is Chivalry Dead??? + Hip Hop Drama 👀 05.06.2026

This week on Cali on the Rocks, Jenn is finally back from Houston and she’s giving us the full recap 🍾 — from the fine Black men 😍 to the drinks, the clubs, and all the shenanigans in between. Let’s just say
 Houston did not disappoint. Then we catch up on the rest of our weekend adventures, including seeing Wale perform in Sacramento and sharing our thoughts on the show. For our main topic, we...

Thirteenth Sip/Episode: Privacy + Relationships + Celebrities We Lost | Dating Outside Your League 29.05.2026

This week on Cali on the Rocks, we’re switching things up with a Ranch Water 🍾 (tequila, fresh lime juice, and Topo Chico) and keeping the momentum going because the grind doesn’t stop! We recorded two episodes in one night, so we skipped the weekly recap and got straight to the topics. First, we dive into privacy in relationships. Do you need your partner’s passcode? Should couples share passwor...

Twelfth Sip/Episode: Non-Sexual Turn Ons + Expensive Dates + Soft Girl Activities 22.05.2026

This week on Cali on the Rocks, we’re keeping it simple with our old faithful margaritas 🍾 (don’t worry y’all, the creative cocktails are coming back soon 😂). We start things off by recapping our Mother’s Day weekend before getting into our first topic: top non-sexual turn ons 😍 because sometimes it really is the little things that matter. In our Take 10, we discuss the report claiming this gen...

Eleventh Sip/Episode: Hot Girl Summer Isn’t Just About Being Outside | Met Gala Looks + Spicy Convos 15.05.2026

This week on Cali on the Rocks, we’re back sipping on our reliable favorite — Carlo Rossi Sangria 🍾 because it’s quick, easy, and definitely gets the job done. After recapping our week, we get straight into our first topic: what does “Hot Girl Summer” actually mean? Why does society automatically connect it to partying, twerking, and heauxing when it can mean so much more? Then we get into the Me...

Tenth Sip/Episode: Girls Trips + Grudges + Growing Up | Still Sipping Through The Chaos 🍾 08.05.2026

This week on Cali on the Rocks, we’re celebrating a milestone — Episode 10!!! đŸžđŸ‘đŸœ Of course we had to pop open another Cutwater (which may or may not have had us feeling loose all over again 😭) and take a moment to congratulate ourselves for making it this far. Thank y’all for rocking with us through all the laughs, hot takes, and chaotic moments. Then we get into our week — Jenn talks about g...

Ninth Sip/Episode: Loose as a Goose 🍾 Zodiac Signs We Don’t Mess With, Dating Woes & Crazy Hot Takes 01.05.2026

This week on Cali on the Rocks, we might’ve started off a little strong
 because that Cutwater Long Island Iced Tea had us feeling loose as a goose real quick. 😳🍾 We kick things off reminiscing about our 20s and the drinks that had us outside — from the Hulk to the Superman to Nuvo
 whew, those were the days. Then we get into our weekly recap — Jenn shares her current struggles with the dating p...

Eighth Sip/Episode: Never Say Never | Spinning The Block + Exes + Surgery Talk 😳💉 24.04.2026

This week on Cali on the Rocks, we’re keeping it simple with margaritas and getting straight into the real conversations. 🍾 After our weekly recap, we ask the question
 would you ever spin the block on an ex? And can you really be friends with an ex, or once it’s done
 it’s done? In our Take 10, we get into the lawsuit involving Live Nation and Ticketmaster — because we definitely want our funds...

Seventh Sip/Episode: Do Men Want To be Courted Now?? | Get It Back In Blood đŸ©ž | Can’t Win For Losin’ 17.04.2026

This week on Cali on the Rocks, we’re feeling a little nostalgic as we sip on some old school Carlo Rossi Sangria and recap our week. 🍾 Then we get into the real question
 would you hit on a guy first, or does he need to shoot his shot? We talk about men being socially awkward in person and why it feels like, at this point, men want to be courted
 and we’re not sure how we feel about that. 🙄 In...

Sixth Sip/Episode: What It Means To Be a Girl’s Girl? | A Real Bitch’s Real Bitch 10.04.2026

This week on Cali on the Rocks, we’re starting things off with a quick recap of our week — including a special shoutout to Jen’s nail tech Holly (IG @hollybae.ig) at Kristin’s Nail & Spa for always keeping her set flawless đŸ’…đŸœ Then we get into our main topic: what does it really mean to be a “girl’s girl”? We break down our definitions, share our thoughts on girl code, and talk about who we belie...

Fifth Sip/Episode: Millennial Teenage Heart Throbs + Hot Takes + “Big Money” Energy 🙄 03.04.2026

This week on Cali on the Rocks, we’re mixing nostalgia with a little confusion
 because what is really going on out here? 🍾 We start with a weekly recap, then get into our thoughts on the Boys 4 Life Tour featuring B2K and Bow Wow — and of course, we had to talk about our throwback heartthrobs 😍 Then we get into today’s dating world and ask the real question
 why are men calling women “big money...

Fourth Sip/Episode: Bad Dates + Good Men Still Exist | Messy Convo With Special Guest D Finesse 27.03.2026

This week on Cali on the Rocks, we’re getting real about dating, nightlife, and everything in between. 🍾 We kick things off with a weekly recap, including a date that didn’t quite hit the way it was supposed to
 and a singles mixer that definitely shifted the energy (because yes, there are still generous men out there 👀). We’re also joined by special guest D Finesse, and the conversation gets re...

Third Sip/Episode: Oscars Looks + Ate or Hate | Controversial Oscar Talk + Top Black Movies |Take 10 20.03.2026

This week on Cali on the Rocks, we’re getting into everything — from the Oscars to culture conversations you don’t want to miss. 🍾 We start with our Oscars recap, breaking down the red carpet and putting these looks to the test in our Ate or Hate segment — because let’s be real
 everybody didn’t eat. Then we switch it up and give you our Top Black movie list, featuring classics like Crooklyn, Boy...

Second Sip/Episode: Gen Z Coming For Millennials They Tried It! Fashion + Shade + Generational Drama 13.03.2026

This week on Cali on the Rocks, we had to address the internet drama — because apparently Gen Z thinks millennials are the worst dressed generation?! Yeah
 they definitely tried it. In this episode we unpack the generational debate, defend millennial fashion, and ask the real question: how are you critiquing us when you don’t even know who Whitney Houston is? In our Take 10 segment, we get into th...

First Sip/Episode: How We Met, Are We The Problem??? Why Y’all Look At Us This Way??? 06.03.2026

Welcome to the very first episode of Cali on the Rocks — where shit gets rocky, but we sip anyway. 🍾 In this episode, we’re introducing ourselves, sharing how we met, and diving into the realities of friendship as millennial women. We talk about how we think people perceive us, how friendships evolve, and what it really means to show up authentically as friends. This is just the beginning — and t...

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