The gals are back with a catch-up episode filled with life updates, new obsessions, and candid confessions!!

Jen shares her big news (spoiler: she’s pregnant again!) while Maddy is catching flights, leaning into a fresh outlook on dating, and calling in her favorite professional organizers (again) to get her life in order.

They close the episode by answering listener questions on everything from navigating dating apps after a long relationship to setting boundaries with in-laws to figuring out when it might be time to let go of a dream.

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Connect with us:

Email us your questions at: hello@areweokay.com
Follow Jennifer on Instagram: @manhattan.wellness
Follow Maddy on Instagram: @downtownbehavioralwellness

Downtown Behavioral Wellness: Founded by Maddy Ellberger, Downtown Behavioral Wellness is a private therapy practice in NYC specializing in Dialectical Behavior Therapy (DBT) and Cognitive Behavioral Therapy (CBT). The practice focuses on providing evidence-based treatments for young adults and middle-aged clients dealing with life transitions, anxiety, and the unique challenges of their 20s, 30s, and 40s. Whether you're grappling with relationship issues, career stress, or emotional regulation, Downtown Behavioral Wellness is there to support you every step of the way.

Manhattan Wellness: Led by Jennifer Teplin, Manhattan Wellness is a boutique therapy practice dedicated to helping young professionals in New York City. Specializing in issues such as anxiety, depression, self-esteem, and major life transitions like dating, engagements, and new motherhood, the team at Manhattan Wellness provides compassionate, individualized care to help clients navigate the ups and downs of their 20s and 30s.

Co-Host: Maddy Ellberger
Co-Host: Jennifer Teplin
Executive Producer: Wicked Child Studio, Hailey Rovner Malach

From career burnout to the pressure of finding fulfillment in your job, the gals break down what it really means to spend 90,000 hours of your life at work and what to do if every one of those hours feels like torture.

They unpack why it’s okay if your job isn’t your passion, the freedom that comes from separating work from identity, and how hobbies, boundaries, and a little creativity can change the way you experience your nine-to-five.

Key Topics:

• Why your career doesn’t have to define you
• Practical tools to cope when quitting isn’t an option
• How comparison at work (and in life) can rob you of joy
• The difference between stepping away vs. stepping toward in a career change
• Dealing with the struggle of money vs. fulfillment

If you’ve ever wondered whether you’re stuck in a cycle of living just for Friday night... this episode might be the reset you need!

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Connect with us:

Email us your questions at: hello@areweokay.com
Follow Jennifer on Instagram: @manhattan.wellness
Follow Maddy on Instagram: @downtownbehavioralwellness

Downtown Behavioral Wellness: Founded by Maddy Ellberger, Downtown Behavioral Wellness is a private therapy practice in NYC specializing in Dialectical Behavior Therapy (DBT) and Cognitive Behavioral Therapy (CBT). The practice focuses on providing evidence-based treatments for young adults and middle-aged clients dealing with life transitions, anxiety, and the unique challenges of their 20s, 30s, and 40s. Whether you're grappling with relationship issues, career stress, or emotional regulation, Downtown Behavioral Wellness is there to support you every step of the way.

Manhattan Wellness: Led by Jennifer Teplin, Manhattan Wellness is a boutique therapy practice dedicated to helping young professionals in New York City. Specializing in issues such as anxiety, depression, self-esteem, and major life transitions like dating, engagements, and new motherhood, the team at Manhattan Wellness provides compassionate, individualized care to help clients navigate the ups and downs of their 20s and 30s.

Co-Host: Maddy Ellberger
Co-Host: Jennifer Teplin
Executive Producer: Wicked Child Studio, Hailey Rovner Malach

Season three is here (!!) and the gals are back and better than ever. After a summer of spontaneous trips, parenting chaos, and the occasional existential crisis, Jen and Maddy are diving headfirst into one of their favorite dating topics: the chase.

Why is it that sometimes not being wanted feels more exciting than actually being wanted?

From the rush of a story view to the infamous “want to be wanted syndrome,” Jen and Maddy break down the psychology of why we get hooked on mixed signals, the role attachment styles play, and how to tell the difference between fantasy and reality when it comes to dating.

If you’ve ever found yourself obsessing over a text or turning a story view into a love letter -- this one’s for you, sis!

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Connect with us:

Email us your questions at: hello@areweokay.com
Follow Jennifer on Instagram: @manhattan.wellness
Follow Maddy on Instagram: @downtownbehavioralwellness

Downtown Behavioral Wellness: Founded by Maddy Ellberger, Downtown Behavioral Wellness is a private therapy practice in NYC specializing in Dialectical Behavior Therapy (DBT) and Cognitive Behavioral Therapy (CBT). The practice focuses on providing evidence-based treatments for young adults and middle-aged clients dealing with life transitions, anxiety, and the unique challenges of their 20s, 30s, and 40s. Whether you're grappling with relationship issues, career stress, or emotional regulation, Downtown Behavioral Wellness is there to support you every step of the way.

Manhattan Wellness: Led by Jennifer Teplin, Manhattan Wellness is a boutique therapy practice dedicated to helping young professionals in New York City. Specializing in issues such as anxiety, depression, self-esteem, and major life transitions like dating, engagements, and new motherhood, the team at Manhattan Wellness provides compassionate, individualized care to help clients navigate the ups and downs of their 20s and 30s.

Co-Host: Maddy Ellberger
Co-Host: Jennifer Teplin
Executive Producer: Wicked Child Studio, Hailey Rovner Malach

Before the gals take a (small) hiatus for the summer - Jen and Maddy reflect on everything this past year has brought them—both on and off the mic. They get honest about what it's like to do a podcast with your best friend, share what they’ve learned (and what they haven’t), and set intentions for the summer ahead. See ya soon! HAGS <3

Connect with us:

• Email us your questions at: hello@areweokay.com
• Follow Jennifer on Instagram: @manhattan.wellness
• Follow Maddy on Instagram: @downtownbehavioralwellness

Downtown Behavioral Wellness: Founded by Maddy Ellberger, Downtown Behavioral Wellness is a private therapy practice in NYC specializing in Dialectical Behavior Therapy (DBT) and Cognitive Behavioral Therapy (CBT). The practice focuses on providing evidence-based treatments for young adults and middle-aged clients dealing with life transitions, anxiety, and the unique challenges of their 20s, 30s, and 40s. Whether you're grappling with relationship issues, career stress, or emotional regulation, Downtown Behavioral Wellness is there to support you every step of the way.

Manhattan Wellness: Led by Jennifer Teplin, Manhattan Wellness is a boutique therapy practice dedicated to helping young professionals in New York City. Specializing in issues such as anxiety, depression, self-esteem, and major life transitions like dating, engagements, and new motherhood, the team at Manhattan Wellness provides compassionate, individualized care to help clients navigate the ups and downs of their 20s and 30s.

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Co-Host: Maddy Ellberger

Co-Host: Jennifer Teplin

Executive Producer: Wicked Child Studio, Hailey Rovner Malach

This week, Maddy and Jen dive into friendship breakups—what it means when a once-close bond starts to shift. They explore when to move on, when to reconnect, and how life changes like sobriety, divorce, or grief can shake up your inner circle.

Key Takeaways:

• Friendships often fade more than they explode—and that’s normal.
• Life transitions (like moving, getting married, or getting sober) can shift who feels aligned.
• It’s okay to reach back out, even after time has passed.
• Not all relationships are meant to last forever—and that doesn’t make them failures.
• You can grieve a friendship the same way you grieve a breakup.

Connect with us:

• Email us your questions at: hello@areweokay.com
• Follow Jennifer on Instagram: @manhattan.wellness
• Follow Maddy on Instagram: @downtownbehavioralwellness

Downtown Behavioral Wellness: Founded by Maddy Ellberger, Downtown Behavioral Wellness is a private therapy practice in NYC specializing in Dialectical Behavior Therapy (DBT) and Cognitive Behavioral Therapy (CBT). The practice focuses on providing evidence-based treatments for young adults and middle-aged clients dealing with life transitions, anxiety, and the unique challenges of their 20s, 30s, and 40s. Whether you're grappling with relationship issues, career stress, or emotional regulation, Downtown Behavioral Wellness is there to support you every step of the way.

Manhattan Wellness: Led by Jennifer Teplin, Manhattan Wellness is a boutique therapy practice dedicated to helping young professionals in New York City. Specializing in issues such as anxiety, depression, self-esteem, and major life transitions like dating, engagements, and new motherhood, the team at Manhattan Wellness provides compassionate, individualized care to help clients navigate the ups and downs of their 20s and 30s.

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Co-Host: Maddy Ellberger

Co-Host: Jennifer Teplin

Executive Producer: Wicked Child Studio, Hailey Rovner Malach

This week, Maddy and Jen are going through their mail bag and answering your questions. From how to handle credit card debt in a new marriage, to whether your political differences can survive the honeymoon phase, to navigating a best friend’s move to the suburbs—we’re covering it all... so, hop on in and join us!

Key Takeaways:

• Lead with how you feel in tough confrontational moments with loved ones.
• DON'T TAKE MEDICAL ADVICE FROM TIKTOK.
• Your values matter more than your politics.
• Friendship isn’t about convenience—it’s about effort.
• If it’s a real fear, treat it like one.

Connect with us:

• Email us your questions at: hello@areweokay.com
• Follow Jennifer on Instagram: @manhattan.wellness
• Follow Maddy on Instagram: @downtownbehavioralwellness

Downtown Behavioral Wellness: Founded by Maddy Ellberger, Downtown Behavioral Wellness is a private therapy practice in NYC specializing in Dialectical Behavior Therapy (DBT) and Cognitive Behavioral Therapy (CBT). The practice focuses on providing evidence-based treatments for young adults and middle-aged clients dealing with life transitions, anxiety, and the unique challenges of their 20s, 30s, and 40s. Whether you're grappling with relationship issues, career stress, or emotional regulation, Downtown Behavioral Wellness is there to support you every step of the way.

Manhattan Wellness: Led by Jennifer Teplin, Manhattan Wellness is a boutique therapy practice dedicated to helping young professionals in New York City. Specializing in issues such as anxiety, depression, self-esteem, and major life transitions like dating, engagements, and new motherhood, the team at Manhattan Wellness provides compassionate, individualized care to help clients navigate the ups and downs of their 20s and 30s.

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Co-Host: Maddy Ellberger

Co-Host: Jennifer Teplin

Executive Producer: Wicked Child Studio, Hailey Rovner Malach

Dating can feel like a full-time job—and when you finally meet someone who seems normal enough, it’s tempting to skip the slow burn and dive in headfirst. But before you have the “what are we?” conversation, Maddy and Jen want you to take a breath.

This week, the gals are breaking down green flags, dealbreakers, and the questions you really need to ask before locking it down.

Three questions to ask before defining the relationship:

• Is it chemistry or compatibility?
• Do we want the same things out of life—at least in the near term?
• How does this person show up when things aren’t easy?

Connect with us:

• Email us your questions at: hello@areweokay.com
• Follow Jennifer on Instagram: @manhattan.wellness
• Follow Maddy on Instagram: @downtownbehavioralwellness

Downtown Behavioral Wellness: Founded by Maddy Ellberger, Downtown Behavioral Wellness is a private therapy practice in NYC specializing in Dialectical Behavior Therapy (DBT) and Cognitive Behavioral Therapy (CBT). The practice focuses on providing evidence-based treatments for young adults and middle-aged clients dealing with life transitions, anxiety, and the unique challenges of their 20s, 30s, and 40s. Whether you're grappling with relationship issues, career stress, or emotional regulation, Downtown Behavioral Wellness is there to support you every step of the way.

Manhattan Wellness: Led by Jennifer Teplin, Manhattan Wellness is a boutique therapy practice dedicated to helping young professionals in New York City. Specializing in issues such as anxiety, depression, self-esteem, and major life transitions like dating, engagements, and new motherhood, the team at Manhattan Wellness provides compassionate, individualized care to help clients navigate the ups and downs of their 20s and 30s.

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Co-Host: Maddy Ellberger

Co-Host: Jennifer Teplin

Executive Producer: Wicked Child Studio, Hailey Rovner Malach

This week Maddy and Jen are diving into a topic that hits hard no matter where you are in life: fertility.

Whether you're partnered, single, child-free by choice, or deep into planning, Maddy and Jen unpack what it means to want (or not want) kids—while confronting timelines, social pressure, and the emotional rollercoaster of egg freezing and family planning.

Key Takeaways:

• Fertility is a mind game as much as a medical one. Whether you're actively trying, freezing your eggs, or not sure what you want yet, the emotional toll of fertility decisions can be intense—and it's okay to feel all of it.
• There’s no “right” timeline. The pressure to hit milestones by a certain age is real, but not always helpful.
• Couples therapy isn’t just for crises. If you and your partner are on different pages about timing, money, or readiness, talking it out before it becomes a problem can make a huge difference.
• Supporting friends through fertility struggles is tricky—but doable.
  Radical acceptance, clear boundaries, and reminding yourself that their pregnancy doesn't threaten your future one is key.

Connect with us:

• Email us your questions at: hello@areweokay.com
• Follow Jennifer on Instagram: @manhattan.wellness
• Follow Maddy on Instagram: @downtownbehavioralwellness

Downtown Behavioral Wellness: Founded by Maddy Ellberger, Downtown Behavioral Wellness is a private therapy practice in NYC specializing in Dialectical Behavior Therapy (DBT) and Cognitive Behavioral Therapy (CBT). The practice focuses on providing evidence-based treatments for young adults and middle-aged clients dealing with life transitions, anxiety, and the unique challenges of their 20s, 30s, and 40s. Whether you're grappling with relationship issues, career stress, or emotional regulation, Downtown Behavioral Wellness is there to support you every step of the way.

Manhattan Wellness: Led by Jennifer Teplin, Manhattan Wellness is a boutique therapy practice dedicated to helping young professionals in New York City. Specializing in issues such as anxiety, depression, self-esteem, and major life transitions like dating, engagements, and new motherhood, the team at Manhattan Wellness provides compassionate, individualized care to help clients navigate the ups and downs of their 20s and 30s.

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Co-Host: Maddy Ellberger

Co-Host: Jennifer Teplin

Executive Producer: Wicked Child Studio, Hailey Rovner Malach