All episodes
Back From Vacation & Spiraling About the Future
Dating Advice I Ignored (And Regret Not Taking Sooner)
From I Do to We Do
Difficult In-Laws, Shared PTO & Relationship Dynamics
I Stopped Dating My Type and Found My Fiancé
Not Fighting Isn’t the Same as Being Close
The Shift, Freedom vs. Stability & My Secret Half Marathon
Career Pt. 2: How I Actually Make Money as a Podcaster & Influencer
We Flew to London for a Surprise Engagement Weekend
My “Dream Job” Paid Me $34K and Broke Me: Part 1 of My Career Story
"Should We Get Married?"
Becoming a Mom at 18 Didn't Stop Me From Living My Life
He Made Valentine’s Day Reservations — Do I Owe Him a Gift?
When Your Friends & Family Don't Support Your Relationship
Losing Yourself in a Relationship and Finding Yourself Again
All Our Friends Are Moving Away & We're Trying New Hobbies
Going on a GLP1 Changed My (Dating) Life
Why Dating Feels Confusing (& What Actually Helps)
Does Our First Date Anniversary Count?
How to Stop Dating Burnout and Start Meeting People IRL
What Not Settling Actually Looks Like
What Happens When You Actually Try to Change Your Life
What It’s Really Like Being a Single Man at 37
Guilt Can Actually Improve Your Relationships
20-Week Challenges, Who Am I Online? & Dating Dilemmas
From Situationship to Marriage: What Actually Changed
When Your First Love Becomes Your Last
The Hard Conversation That’s Making Our Marriage Stronger
45% of Men Have Never Approached a Woman
The Year I Slowed Down: Career Pressure, Marriage & Burnout (2025 EOY Ep)
Proof Love Existed Before Apps
What We Wish We Knew Before Getting Married
How to Spot Red Flags Early with a Former Military Interrogator
Jake’s Year in Review & a Jets Fandom Therapy Session
Life in Your 30s Without a Plus One
What Every Women Needs to Know About Fertility in Her 20s & 30s
Did I End It Too Soon? Dating Regrets & One-Sided Convos
"How EMDR Therapy Saved My Dating Life"
What Your Work Life Says About Your Love Life
Am I Working Hard Enough?
How Losing Her Job Changed Her Entire Dating Life
I Had a Surrogate…and Then I Got Pregnant Too
Why Are Married Men Flirting With Me & Other Mixed Signals
What Dating as a 34-Year-Old Guy Is Really Like
You, Your Husband and His Mother
The Stories We Never Told About Getting Fired
EWhat Moving On and Feeling Secure Actually Looks Like
Are You “Doing the Work” or Just Performing It? with Therapist Rebecca Marcus
Breaking News, Syracuse Recap & How Jake’s Really Doing
Solo Q&A: "Help, My Best Friend Disappeared Into Their Relationship"
The Love Story You Didn’t See on Love Is Blind
Is Having A Boyfriend Embarassing?
What If You Haven’t Been Loved the Way You Deserve Yet?
What Running The NYC Marathon Actually Felt Like
What Healthy Intimacy Actually Looks Like (& How To Built It)
Why Men Are Getting Dating Wrong—And What Women Actually Want
Unlearning The Dating Rules That Are Keeping You Stuck
Jake’s First Kiss & Other Things He Never Talks About
How to Get Over A Crush
Should You Stay or Should You Go?
My Friend Hooked Up With Someone’s Boyfriend — AITA?
“What It’s Really Like to Be Single at 49”
EA Closer Look at Women's Health
“Sure, I Love Football” and Other Dating Lies We All Tell
Am I Settling or Just Being Realistic?
The Art of Good Communication
Flying to Italy & a Listener’s Emotional Cheating Confession
How Our Friendship Survived Different Life Stages
The Anti-Anxiety Approach to Modern Dating
What We Wanted to Be When We Grew Up vs. Kids Today
How To Date Intentionally This Cuffing Season
Why Some Couples Divorce and Others Find Their Way Back
Our New Home & Our Unpopular Take on Wedding Speeches
From Finance Bro to Full-Time Musician: Owning Your Story in Dating
What Happens When You Sit Down With All Your Exes
Should You Reach Back Out or Let Them Go?
Answering Your Biggest Dating & Friendship Dilemmas
Dating Burnout, Rock Bottom, and the Power of Being Alone
Fall Date Ideas That Don't Suck
“He Cheated, Got Someone Pregnant… and Then Called Off Our Wedding 2 Weeks Before”
Falling In Love & Designing Her Dream Life 5000 Miles From Home
Would We Have Found Love on Reality TV?
My Running Journey: From Hating Running to Training for the NYC Marathon
Is Everyone a Narcissist Now?
The End of an Era
“I Almost Let My Body Image Ruin Everything — Including My Wedding”
Recovering From Infidelity: Can Love Survive Betrayal?
What Would 13 Year Old Us Think Of Us Now?
Trust Your Gut, Not Your Group Chat
What If You Don’t Want the Life Everyone Else Has?
How the Jonas Brothers Were Our Matchmakers
I've Never Been In A Relationship Before
Choosing Myself After the Breakup
Is Traveling Without Your Partner a Relationship Red Flag?
Love Won’t Fix You — But These Things Might
If This Was Your Friend’s Relationship… Would You Be Worried?
Relationship Milestones & How Our Love Story Almost Didn’t Happen
Trying to Get Pregnant While Trying Not to Fall Apart
"You’re a Nice Guy, But…" Dating Horror Stories
Why We Track Every Date — and You Might Want To