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

Ever caught yourself pretending to be a Deadhead just because he is? Guilty as charged.

This week, Maddy and Jen unpack just how much we let other people’s opinions influence the way we show up—on Instagram, on first dates, and even in our own heads.

Why do we shape-shift to please others? Who are we really trying to impress? And how do we know when we’ve crossed the line from harmless tweaking… to full-blown personality catfishing?

Key takeaways:

• You don’t owe the world access to your inner world.
• Having a cringe worthy moment is totally human. And, trust us, the only person ruminating about it is YOU.
• The goal isn’t to be liked by everyone— if you like yourself 60% of the time you're winning at life.
• Opposite action to shame = the antidote to self-editing.

Key takeaway from Maddy:

• Always check the UV index, always wear sunscreen!!!

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