All Episodes

My Boyfriend's Side Hustle Is Ruining Our Relationship

Why is My Ex-Fiancé's Profile Picture My Dog?!

Does He Just Want a Wife?

Bumble’s New AI Matchmaker “Bumblebee” Explained

Can Someone Truly Change After Cheating?

Dr. Orna On The Biggest Mistake Couples Make

Should You Tell Your Ex You’re Pregnant?

Married a Gay Man… And We’re Completely Monogamous ft I Married a Gay Man

Is a Breakup Revenge Post Ever Okay?

He Won’t Go To Therapy But Says I’m the Problem

The “Girl You Don’t Need to Worry About” Problem

Why Hot Takes Are Ruining Dating Advice ft. Dear Shandy

Ryan Seacrest’s Dating Red Flags Make No Sense

Should You DM the Girlfriend If You’re the Other Woman?

He Matched With Me… And My Brother! A Dating App Nightmare

What’s the Right Way to Approach Someone IRL?

The Moment His TikTok Fame Ruined the Date

My Friend & My Ex Are Hooking Up!

Why Situationships Hurt More Than Breakups

Follow These Rules For Meeting The Family

What Changes In A Relationship After Kids?

My Partner Makes Me Feel Stupid… Now What? ft Emma Willmann

I Dumped Him in Public So He “Wouldn’t Make a Scene” ft Tiff Baira

What Are the Rules of an Open Relationship? ft Ashley Gavin

Is “Right Person, Wrong Time” Actually Real? ft Logan Ury

I Love My Boyfriend But I’m Scared To Move In Together

The Silent Relationship Killer you CAN Avoid ft Aleen Dreksler

Is He Avoiding Sex On Purpose? ft Dr. Naomi

Would You Date Someone With 2 Boyfriends? ft Bob The Drag Queen

Should You Break Up Over Bad Kissing?

Is A 14 Year Age Gap Too Much? ft Yamaneika Saunders

He Cheated for Almost a Year — How She Finally Found Out

He Fights Dirty With His Family—Will He With Me? ft Matteo Lane

Why Dating Feels So Negative Right Now ft. Matchmaker Maria

When Body Image Becomes a Dating Issue ft. Sami Sage - Co Founder of Betches

He Dumped Me Because Of My Music Taste?!

Why Money Conversations Matter Early in Dating ft Vivian Tu

He’s 24, I’m 37 - Can We Really Be In Love?

I Can’t Stop Comparing Myself to His Ex!

Coming Out After Kids ft Chris Appleton

My Ex Wants Our Dog Back

How to Spot Swinger Signals

We're Engaged, So Why Am I Still Hidden on His Socials?

Would You Date Someone With Immature Friends?

Is Publicly Exposing Cheaters Wrong?

The Biggest Dating Week of the Year

New Year, New Dating Rules

Is Saying Your Dog is your Kid an Ick?

Is Christmas A Relationship Test?

Is a Boudoir Shoot As Christmas Present a Good Gift?

Who Covers Travel Costs After a Breakup?

Why Your Ex’s Instagram Still Messes With Your Head

How Old Is Too Old To Be Gaming?

Will Jeff Bezos and Lauren Sánchez's Relationship Survive 2026?

When Is Too Early To Reveal A Kink?

Should I Break Up Before or After the Holidays?

How to Answer ‘Why Are You Still Single?’

How Do I Navigate My New Polyamorous Relationship?

Jennifer Lawrence’s Secret TikTok a Red Flag?

8 Years of U Up? Our Wildest and Most Iconic Moments!

Is Saying 'Boyfriend' Cringe?

Dating Titles: Exclusive vs Boyfriend

How to Know You’re Ready to Move In

Did Selena Gomez and Benny Blanco Win Halloween?

Halloween Reveals Your True Relationship Status

Have These Dating Trends Gone Too Far?

Mom Kisses Son, Major Ick

Is the Pen Pal Dating Trend Back?

How To Date Someone Outside Your Faith

You’ve Got Mail: The OG of Online Dating

When Is the Right Time to Share Your Number?

It's Taylor Swift & Mean Girls Day!

30 Taylor Swift Shows Later… Red Flag?

Is Selena Gomez “Shrekking”?

How to Date Your Roommate

I Spoke to My Partner’s Mistress & This Is What She Told Me ft Dateable Podcast

Taylor & Travis Got Engaged, Now You’re Panicking

Is It Rude to Ask For a Plus One?

How to Survive a Sports-Obsessed Partner

Are Men Wearing Shoe Lifts an Ick?

Decoding Weird Boyfriend Habits

How to Get Deep Without Scaring Your Date ft. Kat Sadler

How To Date On A Budget

Spotting the Lies Before You Swipe ft. Kamie Crawford

Am I Dating A Disney Adult?

Whitney Cummings Breaks Down Toxic Behavior & Real Friendships

How to Date Intentionally When No One Else Is

Long-Distance Love or Just Bad Timing?

How To Clean Up Your Feed After a Breakup

Does 'The Materialists' Hate Matchmakers?

Is It Okay to Date Your Brother’s Best Friend?

Too Soon to Reveal Feelings?

Is Going Out Alone a Red Flag?

How Long Is Too Long to Be Single? ft. Gals on the Go

He Calls His Mom Every Night?!

Who Really Deserves an Apology After a Breakup? ft. Atsuko Okatsuka

Can Weight Gain Change Your Relationship?

Are You Settling or Leveling Up?

Banned From Hinge for Ending It After Date 3

The Rom-Com That Could Never Be Made Today

Is LinkedIn the New Dating App?

Do You Really Need Instagram to Date?

How to Nail the First Date Look

Hinge Warned Me She Was a Scammer!

Speed Dating Tips You Need to Know for a Second Date!

Tired of the Apps? Try This Summer Challenge

His Mom Helped Him Break Up!

Where Are All the Eligible Men?

Divorce Drama: Should the Side Piece Pay?

Matchmaker's Guide to 'The One' ft. Matchmaker Maria

Do First-Date Kisses Ruin Long-Term Potential?

Are West Village TikTok Girls Ruining NYC?

Can You Judge a Date by Their Scent?

Is It Chemistry or Friendship? Exploring New Relationships with Maren Morris

Can You Be Jobless AND Dateable?

Is My Honesty Driving People Away?

Can I Be In Love Without Being In Lust?

I Stole My Exes Baby Name, AITA?

He Hardly Says 'I Love You'... Should I Be Worried?

Jay Shetty Pep Talks the Group Chat

How Do I Tell My BF He Has Bad Breath?

Can You Date Outside Your Socioeconomic Status? ft. Dr. Jaimie Glick

How To Ask Your Friends To Set You Up

Peloton, Playbills & Petty Moves with Cody Rigsby & Andrew Chappelle

Chelsea Handler Ghosted by Andrew Cuomo?!

When Should You Archive A Pic Of Your Ex?

Why Won't Men Approach Women Anymore?

How To Clean Up Your Life ft. Summer Rose

When Is It Too Soon to Post About Someone?

I Exposed My Cheating Ex

My Ex’s New Girlfriend Moved In Next Door

I Gave Him Everything...Then He Dumped Me Ft. Spritely

How Your Dating Profile Is Keeping You Single

How To Manage Dating an Over-Texter

Make a Follow-Up Date or F*ck Off

I Got Dumped The Day After Our Anniversary

When Does A Partner’s Joke Go Too Far?

What It’s Really Like in the Netflix’s "Love is Blind" Pods

Can I Spend Valentine’s Day With My Situationship? (Lightning Round Special)

Should I Go No Contact With My Ex?

Is My Buff Body Scaring Away Men?

Why Won’t My Partner Initiate Sex?

Bachelor Blindside: Matt James & Rachael Kirkconnell Split

How Do I Approach My Gym Crush?

If Carrie Bradshaw Is The Worst, So Are You

Avoidant Discarding: The New Ghosting?

Do I Want A LDR For The Wrong Reasons?

Casual Dating, Demanding Careers And Dating In A New City

How Can The Let Them Theory Help Me? ft. Mel Robbins

Did I “Win” The Breakup?

Am I Really Undateable? Ft. Logan Ury

Spot Red Flags & Avoid Bad Dates In 2025

How Soon Should I Ask Their Salary? ft. Ramit Sethi

Will Cheating Karma Catch Me In My Next Relationship?

What Will 2025 Bring My Zodiac Sign? ft. Kelley Knight

How Do I Date While I’m Home For The Holidays?

Dating Pulse Check: Should I Invest Or Move On?

Is It Too Early To Be Annoyed With The Person You’re Dating?

Jared Saw His Soulmate And Now He’s Scared

Post-Date Confusion And Why We’re Happy For Selena Gomez

Modern Dating: Why ChatGPT Should Edit Your Breakup Text

Lightning Round: Navigating The Holidays With A SO

Cuffing Season: Signs Of Casual VS Committed

Cuffing Season, Casual Sex And Dating Complications

The Seven-Year Itch: The Anniversary Episode

Is The "Single Mindset" In A Relationship Real?

Politics, Dog Poop, and Whiskey Dick

Should I Ask My Hot Doctor Out?

Is It Romantic Or Creepy To Track Down An Old Match?

Halloween Hookups & Costume Red Flags

My Boyfriend Loves To Vape And I Hate It

Why Do My Dates Keep Canceling On Me?

Is It Weird That My Boyfriend Doesn’t Post Me?

I Hate When Other Women Compliment My Fiancé

My BF Is Divorced And Still Healing

Rematching On The Apps & Keeping Exes Around

Should I Take Him Back Now That He’s In Therapy?

The Best And Worst Cities To Date In 2024

Just Because You Got Engaged Doesn’t Mean You Should Get Married

Why Does My BF’s Stability Turn Me Off?

Heather Graham's Affirmations Helped Me Find A Husband ft. Heather Graham

I’m Turning Into My BF’s Mom And I Hate It

Is Sexual Compatibility A Valid Reason To Break Up?

Is He Really Busy Or Is It Just An Excuse To Pull Away?

I’ve Been Engaged Three Times, Why Can’t I Get It Right?

How Honest Should I Be With My Date?

How Do I Deal With A Crush While My Boyfriend Is Long Distance?

Is A Bad Weekend Enough To Break Up With My Boyfriend?

Instagram Breakups & Girl Code For Friends' Exes ft. Kaitlyn Bristowe

Lightning Round: How To Deal With A Football Obsessed Partner

Compromise Is For Couples

The Pros And (Mostly) Cons Of Going On A Dating Show

My BF’s Sense Of Humor Gave Me The Ick

How Do I Talk To My SO About Grief? ft. Dr. Naomi Bernstein

Why Do Exes Compliment You During A Breakup?

Easy Ways To Let Your Date Know You Like Them

Don’t Skip This Step When You Delete Your Dating Apps

Is It My Responsibility To Train My BF?

Ho Phase Appreciation And A Realistic Look At Married Life ft. The LadyGang

Why Love Island’s Casa Amor Isn’t A Real World Risk

The Urge To Win The Breakup

It’s OK To Lie On Dating Apps Sometimes

How To Be A Better Dating Consumer Of Men

The Economics of Dating

I Dated Like It Was A Job ft. Rachel Feinstein

Am I Being Too Emotionally Slutty For My Partner?

I Had A Meet-Cute With A Man In Finance

My Guy Friend Confessed His Feelings, So I Ghosted Him

The Fine Print Of #DatingTok Advice

Coming To Terms With Your Kinda-Ship

My Mom Is In Her Divorced Era. How Can I Help Her Date?

I Love My BF, But He Hates My Dog

Love, Limerence, And Cop Outs ft. Olivia O’Brien

They Always Come Back For The Wrong Reasons

Should I Tone Down My Personality To Attract More Dates? ft. Emma Willmann

The Curse Of The Cool Girl

Why Being Mad About A Wasted Relationship Isn’t Helping You

A Friends-To-Lovers Story Gone Wrong

My Husband's Ex Is Being Petty. Can I Be Pettier?

Can I Turn My Friend-To-Lover Back Into A Friend?

Why The “When You Know, You Know” Spark Might Be Missing ft. Matthew Hussey

Could A 'Certified Lover Boy' Ever Commit?

The Situationship Cycle ft. Dulcé Sloan

Where Does A Digital Affair Fall On The Cheating Scale?

Can I Force A Closure Conversation After A Breakup?

I Took My Ex Back and He Dumped Me—Again!

Should It Matter That My BF’s Mom Dislikes Me?

Are Some Women Doomed To Be Alone Forever?

Can You Be Partners In Love And Business? ft. Nick and Elyse Oleksak

Is It Just Me Or Is The Dating Pool Polluted?

Feng Shui, Dating Intentions, & Jared’s Sh*tty Energy ft. Jeannette Cieszykowski

What Is The Right Way To Compliment A Man?

Erotic Energy, Rethinking Infidelity, And Psychotherapy ft. Esther Perel

The Worst Kind Of Rematch on Hinge

A Message To Cheaters

AITA For Thinking You’re Full Of Sh*t?

SOS: I've Invested Too Much In A Dead-End Situationship To Walk Away

If It’s Giving Boyfriend, Just Say That

Is Jared Just Like The Bachelor? ft. Joey Graziadei

When To Walk Away From The Person You’re Dating

How To Break Up Like A Gentleman

Was This A Red Flag Or Is My Internalized Homophobia Showing?

I Hate My BF’s Therapist

V-Day, TikTok Backlash, And Where The Single Men Are

Bland DMs: Why You Might Be The Problem

Get Pookie TikTok Away From Us

Icks Are Ruining Dating ft. Jay Shetty

Failures Make You A Better Dater

SOS: Does My Ex Want Me Back Or Is She Messing Around?

What’s Wrong With Settling?

The Hard Truth About Getting “The Ick”

How Much Does Your Past Impact Your Dating Future?

Beware Of Breakup January

Are You Dating An Aidan Or A Mr. Big?

How I Got Engaged After 6 Months Of Dating ft. Rosebud Baker

Did Jared Find Love On His Blind Date?

Rizz, Sober Dates, And Dating In 2024

It’s The Week Of Nothingness

Toxic Exes, Moms, And Ruining Christmas

Who Won The Date With Jared?

Rejections Are Good For You

The Problem With Playing It Cool

Should I Be Cleaning My Boyfriend’s Apartment?

You Want To Be The Prize, Not The Pick Me

Crystals, Spells, And WTF Is Up With Jared ft. Kelley Knight

Your Words Are Like Spells: Cheating, Standards, and Situationships

The Love Of Your Life Is A Teammate, Not A Goalpost Ft. Vir Das

‘Tis The Season For Hometown Hookups

SOS: Insecurities Are Cockblocking My Dating Life

Thanksgiving Prep: Is It Too Early To Invite My SO?

6 Years, 500 Episodes, And More Dating To Solve

When The Honeymoon Phase Ends, What’s The Next Step?

Jared VS Jorge: Is Jared Really 10% Away From All Men?

Is Caspering The New Ghosting? (Debating This Year’s Spookiest New Dating Terms)

How Honest Should You Be During A Breakup? Ft. Sam Morril

Dating Is So Much Easier Now That I’m Married

Dating When You Don’t Want Kids ft. Girls Gotta Eat

The Problem With Dating Dog People

It’s Not Your ADHD, You’ve Got Dating App Fatigue

Bumble’s New Update: Isn't This Just “Love Is Blind”?

37, Single & Gay ft. Emma Willmann

Why Does My BF Keep Backing Out Of Plans?

My Interracial Relationship Isn’t An Insult ft. Nimesh Patel

Introducing: Ask Men Anything with Emma Willmann (Ft. Jared Freid)

Can You Be Old-Fashioned In A Modern Dating World? Ft. The Golden Bachelor

And Just Like That, We’re In A New Season Of Love

You Can’t Find A Date Because You’re Missing The Point

Surviving Your Family Trip As “The Single One”

How To Tell If It’s A One-Sided Setup

Nothing Good Comes From Keeping Your Ex Around

My Boyfriend Doesn’t Want Kids, But He’s A Father

Sometimes, You’ve Got To Take The “L”

Lightning Round: How Do I Know If They’re “The One”

Does Cheating Once Make You A Cheater For Life?

Who’s Responsible For Texting After The Date?

My Exes Don’t Exist To Me Ft. Sasheer Zamata

The Unspoken Rules Of Arguing With Your SO

Should I End My Situationship Before It Gets Serious?

Does A Small Age Gap Still Make Me A Cougar?

How Petty Are Exes Allowed To Be?

Can A Relationship Ever Survive A “Break”?

Is It Fair To Ask Your Partner To Subsidize Your Dreams?

How Do I Get Over A Breakup If Nobody Was The Villain?

Can You Really Be Friends With An Ex? Ft. Robyn Schall

How Bad Were Jonah Hill's Texts Really?

Some Dishonesties Are More Dangerous Than Others Ft. Dr. Drew

I’m Single And Happy, But Should I Try Dating Anyway?

Enough With The Beige Flags

Your Issue Isn’t Your Baggage, It’s How You Address It

You’re Putting Too Much Pressure On The Penis Ft. Dr. Emily Morse

What’s An Appropriate Age Gap?

Husband Or F*ck Off: What Happened Next?

How Long Should I Wait For Him To Propose?

You’re Wearing The Wrong First Date Outfit Ft. Liza Lieberman

Announcement: Subscription Update!

What’s A Socially Acceptable Way To Ghost?

Rejection Isn’t Always As Deep As It Feels

What Are The New “Love Languages?”

What’s The “10-Monther” Timeline?

Scandoval And The Audacity Of Men

Heather McMahan’s Guide To Relationships

How Do I Know If I'm Ready To Date Again?

Is He Self-Sabotaging Or Does He Just Not Like Me?

Why Can’t I Make It Past A 3rd Date?

Is Lust Worth Risking A Friendship?

Is Being Exclusive Different Than A Relationship?

Is He That Busy Or Am I A Benchwarmer?

Getting Your Situationship To The Next Level

Is It Okay To Play Games In Some Dating Scenarios?

Why Do I Keep Getting Textzoned?

We Matched, We Connected, He Canceled

Does Your Parents’ Opinion Of Your S.O. Actually Matter?

Behind The Scenes Of A Set Up By Jordana

Am I A Rebound Or Is He Ready To Move On?

How Much Does Your Resume Matter On The Apps? Ft. Jesse Metcalfe

Am I Insecure Or Is He Being Inappropriate?

The Dating Mistakes Everyone Makes

Blindsiding Is A Spectrum Ft. Rebel Wilson

SOS: Can We Be Just Friends If We Made Out?

The Betchelor Crossover: Love Is Blind Eps. 1-2: The Beginning

Am I More Invested In The Relationship Than My BF?

Does Swiping Count As Cheating? Ft. Adam Pally

Why Are Situationship Breakups So Painful?

Why You Should Have A Roster Ft. Violet Benson

The Problem With #DatingTok

SOS: How To Make First Dates Feel Less Like Interviews

Breadcrumbing, Cookie-Jarring, & Cobwebbing: Dating In 2023

Is It “Limerence” Or True Love? (Oversharing Sneak Peak)

So Jared, Why Do Men Say Things They Don’t Mean?

Lightning Round: Do Men Hate Situationships As Much As Women?

SOS: Husband Or F*ck Off

How Much Can You Embellish On Your Dating App Profile?

Valentine's Day Dates: The Archive Dive

Nothing Happens When You Least Expect It Ft. Jay Shetty

Was Your DTR Talk Too Vague?

Do You Need To Be Single To Work On Yourself?

What Counts As Cheating?

SOS: Blindsided By A Breakup

Is Ambition A Valid Reason For A Breakup?

Why Can't I Commit To A Fifth Date? (Jared's Oversharing Therapy Session)

The Problem With Being Comfy

How To Revive A Dating App Match

Don’t Fall For A Selfish Apology

How Much Does Sexual Chemistry Matter?

Playing It Cool Is Overrated

How To Be More Charming

You’re Not Annoying, He’s Just An Asshole

Make Your Dating Life About You

What Does Emotional Availability Actually Look Like?

Does Splitting The Check On The First Date Mean He’s Not Into It?

To Play Games Or Not To Play Games

How To Ask For More Romance In A Relationship

Was He Using Me Or Did He Just Change His Mind?

Are You Too Picky Or Not Picky Enough?

How Gender Norms Are Hurting Your Sex Life Ft. Emily Nagoski

Do I Need To Live In A City To Date?

How To Deal With Weird Texts From An Ex

Sliding Vs. Deciding

Do You Have To Like Your S.O.’s Friends?

The Anniversary Episode

Can Family Dynamics Be A Deal Breaker?

Why Won’t My Friends Set Me Up? Ft. Fortune Feimster

Do You Have To Reply To A Breakup Text?

Why Doesn’t He Ask Me Any Questions?

Why Do Men Make Promises They Can’t Keep? Ft. Delaney Rowe

Is “He’s Just Not That Into You” Still Accurate?

How To Talk About Money With Your S.O. Ft. Ramit Sethi

Am I Giving Up If I’m Not On The Apps?

Stop Romanticizing Your Ex

Do Guys Care Less Once It’s Official?

Should I Reach Out Again If The Timing Wasn’t Right?

Lightning Round Part 2: Embracing Disappointment, The World’s Saddest Pep Talk, and Romantic Coffee Dates

Will Losing Weight Fix My Relationship?

Lightning Round Part 1: Adam Levine, Standing Out On Dating Apps, & Living With A Disgusting

What Should You Expect When Visiting A Long Distance Fling?

How Much Time Do You Need Between Relationships?

Are You Dating Like You’re In A Relationship?

How To Avoid Dating App Burnout

How Secure People Respond To Rejection

How To Take The Pressure Off Of Your Dating Life

Are Work Crushes Hurting My Love Life?

“The Rise Of Lonely, Single Men”?

Can You Trust A Drunk Text?

Should I Join A “Are We Dating The Same Guy?” Facebook Group?

How Much Vetting Is Too Much Before A First Date?

Would You Want To Be On A Singles List?

Do You Actually Want To Know Why They Ended It?

Am I Trusting My Gut Or Being Judgemental? Ft. Zoey Deutch

Stop Worrying About The Friend Group

What’s The Right Texting Ratio?

Can Height Be A Deal Breaker? Ft. Patti Stanger

Can I Ask My BF To Clean Out His Following List?

Do Men Avoid Hookups To Avoid Blame?

It’s Not You, It’s Your Explore Page

Are Men Really Intimidated By Me?

What Do Men Actually Mean When They Say They’re Not Ready?

How Is He Not Thinking About The Future?

Does The “Crazy/Hot Scale” Still Hold Up?

“Better Than Nothing” Relationships Are Actually Worse Than Nothing

Is It Inflation Or Is He Just Not That Into Me?

How To Spot A Guy Who’s Just Telling You What You Want To Hear

How To Block Someone In An Empowering Way

Should You Pre-Qualify Your First Dates?

Can You Wait TOO Long To Have Sex?

Should I Call Out A Vibe Shift In My Relationship?

What’s More Important, Chemistry Or Connection?

Vague Questions Get Vague Answers

How To Do A Mini Reveal

How Should I Interpret Confusing Communication From My Ex?

What’s The Right Answer To “How Are You Still Single?”

How Do I Stop Comparing Myself To My Boyfriend’s Ex?

Is The Saying “When You Know You Know” Actually True?

Is This A Red Flag Or Am I The As*hole?

When Does A White Lie Become A Regular Lie? Ft. Rebel Wilson

How To Take The Hint After Shooting Your Shot

Dating Before & After College

“The Ultimatum” Review

How To Weed People Out On The First Date

You Can’t Hack The Dating Apps

The Key To A Better Dating Life Is Your Life Outside Of Dating

Does Being "Adventurous" Mean Putting Up With No Effort?

Is It A Good Sign If A First Date Lasts a Long Time?

Are Men Intimidated By Women’s Success?

Better App Conversations Come From Better Prompts

Men Picture The Breakup, Women Picture The Wedding

The Upside Of A “Failed” 3-Monther

Is Ghosting Ever Okay?

The Only Dating Rules That Matter Are Your Own

Temporary Relationships: Every Man’s Dream?

Is Instagram The Ultimate Relationship Test?

Is Sliding Into The DMs Less Creepy When Women Do It? Ft. Taylor Tomlinson

Is Going On Dates The Same As Dating? Ft. Sebastian Stan & Daisy Edgar-Jones

Is Timing a BS Excuse?

Closing The Sexting Gap

Is The Instagram Follow A Big Deal In Dating?

How Do I Stop Being A “Cool Girl”?

Does Acting “Coupley” Actually Mean Anything?

Winter Dating Pep Talk

Can We Still Be Friends If He Wants To Hook Up With Me?

Valentine’s Day Lightning Round: Embrace The Cliché

“And Just Like That...” Season Review

Will Men Settle Down With Literally Anyone If The Timing Is Right?

Does Anything Justify Not Texting Back For Over A Week?

How NOT To Do Long Distance Relationships

West Elm Caleb Is Everything That’s Wrong With Modern Dating

Stop Judging Yourself So Much When Dating

Can Awkward Sex Be A Deal Breaker?

Is It Normal To Have FOMO When You’re In A Relationship?

It’s Okay To Admit You Don’t Want Something Casual

Is It A Red Flag If My Boyfriend Stays In Touch With His Ex?

Is It Possible To Separate A Potential Love Interest From Their Income?

What Does “Settling” Actually Mean?

Why Do Some Women Reject “Sweet” Guys?

Jordana’s Wedding: A Dramatic Reading (U Up? With Benefits Excerpt)

Does Every Situationship Deserve A Breakup?

Why Does He Keep Texting Me Without Planning A Date?

Does It Matter How Many People They’ve Slept With Before You?

All Too Well (Taylor’s Version) (J&J’s Version)

Jared Reviews Jordana’s Wedding

Do I Really Need My Stuff Back From My Ex?

You Are Your Explore Page

When To Take The Loss In Dating

The Pros & Cons Of Meeting On The Apps

How To Handle A Breakup With A Coworker

Lightning Round: Thanksgiving Invites, Holiday Gifts, And Nosey Family Members

How To Stop Wasting Time On People Who Aren’t Making You A Priority

Do Exes Always Come Back? Ft. Ricky Velez

When Should Couples Start Mixing Finances? Ft. Berna Anat

Is Dating Easier For Men?

The Best Way To Approach Failed Situationships

What Is “The Reveal”?

How To Cut Ties With The Guy In Your DMs

How To Talk To Your S.O. About Sex

How To Write An Effective Standard-Setting Text

What Are The Signs That You’re In Love?

When Is It Okay To Have A Serious Conversation Over Text?

How Dating Buzzwords Might Be Hurting Your Love Life

Am I The F*ckboy?

Would You Really Want To Know Why Someone Broke Up With You?

How To Confront Your S.O. About Sketchy Texts

How To Know If You’re A Rebound

Are Different Political Views A Deal Breaker?

Can I Be Confident And Insecure At The Same Time? Ft. Violet Benson

What Does A F*ckboy Get Out Of Being Friends?

What To Do When You Let Your “Crazy” Show Too Soon Ft. Giannina Gibelli

How Long Is Too Long To Wait For A Text Back?

Should I Accept A “Hangout” Date?

What You Should Ask Yourself Before You Break Up Ft. Logan Ury

Lightning Round: Dating In The Age Of Social Media

Does Playing Games Ever Work?

Why Would He Act Like My Boyfriend But Not Want To Date?

Can You Set Your Standard Too Low?

How To Date Multiple People At Once

When Is It Time To Block Someone?

What Does Being A F*ckboy Actually Mean?

Your Love Language Is Whatever You’re Getting The Least

Is Cheating Always A Deal Breaker?

How To Date In Your Twenties Ft. Dr. Meg Jay

Why Am I Offended If I Don't Even Like Him?

How To Know If The Timing Is Off Or If They're Just Not That Into You

Lightning Round: Your Summer Dating Questions Answered

What To Do When You Catch Feelings And They Don’t

Why Don’t My Friends Like The Guy I’m Seeing? Ft. Iliza Shlesinger & Margaret Cho

Am I Settling Or Did I Just Find The Right Person Early? Ft. Lori Gottlieb

How To Tell If A F*ckboy Has Actually Changed

Am I Being Avoidant Or Do I Just Not Like Him?

How To Keep Your Summer Fling From Fizzling Ft. Jared’s College Ex, Ashley Bisman

Should I Call Out A Breadcrumber?

Is It Weird To DM Someone If You Didn’t Match On The Apps?

Is Infidelity Inevitable? Ft. Dan Savage

Do I Have What It Takes To Have A Hot Girl Summer?

Why Do Exes Come Back Pretending To Want Friendship

Lightning Round: Dating App Pictures, Bad Kissers, And Emotionally Slutty Boyfriends

Are Personality Types Relevant In Dating?

How To Hit On Someone Without Being Creepy Ft. Camille Kostek

Is Alcohol F*cking Up My Dating Life?

Dealing With A Breakup

How To Tell Your Best Friend You Have Feelings For Them Ft. Tinx

Will My Relationship Survive After The Pandemic?

A Matchmaker’s Guide To Finding Love Ft. Matchmaker Maria

Is Faking An Orgasm Anti-Feminist?

Not Everyone Who Doesn’t Want To Date You Is A F*ckboy

How To Have Casual Hookups Without Feeling Disrespected

Is My Coworker Flirting Or Just Being Friendly?

What You Should Know Before You Pay For Dating App Features

Is He Bad At Planning Or Does He Just Not Care?

Are You Setting Your Standards Or Avoiding Rejection?

How To Spot a Lazy Dater Before You Get In Too Deep

Lightning Round: Dating App Tips, F*ckboy Streaks, And Running Into Exes

Why Do People Still Get Married?

How Long Should It Take For Them To Say “I Love You”?

Am I An As*hole If I Keep Hooking Up With Someone Who Has Feelings For Me?

Can You Call Dibs On A Dating App Match?

How Many White Lies Make A Red Flag?

Do I Really Want To DTR Or Is It Just Relationship Anxiety? Ft. Victoria Justice

How To Ask For What You Want In Bed Without Offending Your Partner Ft. Dr. Emily Morse

Should I Wait To Break Up Until It’s More Convenient To Move Out?

How Do I Know If The Person I'm Dating Is Ready To Move On From Their Ex?

How To Apologize To An Ex You Treated Poorly

Is It Ever Worth Trying To Make It Work With a Bad Communicator?

How To Set The Expectation That You Won’t Be Hooking Up Before A Date

How To Get A Straight Answer About Why Your Fling Suddenly Ended

Can I Ask My Partner To Pay More If They Make More? Ft. Mike Johnson

How Do I Tell My New Partner About My Food Issues? Ft. Aleen Dreksler

What Are The Valentine’s Day Expectations In A New Relationship?

How To Not Die Alone Ft. Logan Ury

Is There A Way To Salvage A Relationship With Very Different Marriage Timelines?

How Many FaceTime Dates Equal One IRL Date?

How To Get Your Parents To Stop Pressuring You To Date

Everything You Need To Know About Dating With Herpes Ft. Erica Spera

Should I Tell Him I Snooped On His Phone If I Didn't Like What I Saw? Ft. Stephen Colletti & James Lafferty

Does An Expensive Date Imply That He Wants A Relationship Or Sex?

Is It Normal To Keep Track Of Every Date You’ve Been On?

How To Spot An A*shole Who’s Pretending He’s a Nice Guy

Is There Ever A Chance A Long Term Hook Up Can Turn Into A Relationship?

Is It a Bad Sign if He’s Saying He Doesn’t Want to See Me Until the Pandemic is Over?

How To Move On In The Midst Of A Pandemic

How To Get A Guy Who Won't Date You To Stop Looking At Your Instagram Story

How Do I Get Over An Ex Moving On Too Quickly? Ft. Bo Burnham

Is It Possible To Turn An Out-Of-Town Fling Into Something Real?

Here Are The Signs That Your Boyfriend Is Trying To Break Up With You

Does A Random “How Are You?” Text Mean They’re Looking To Hookup?

How Do I Relay That I Want An Expensive Engagement Ring Without Seeming Shallow?

Why Would An Ex Swipe Right On My Dating Profile?

Is It Okay To Judge Someone You're Dating By Their Friend Group?

These Are The Signs You Shouldn’t Go On That First Date

Do I Have a Right To Ask The Guy I'm Seeing Why He's Following Girls On Instagram?

Is It Worse To Be A Cynical Dater Or A Naive Dater?

How Soon Should You Expect To Get Daily Messages From A Person You Started Dating?

Does It Count As Cheating If He's Getting Nudes From Someone He Never Met?

Is It a Dealbreaker If Your Significant Other Won’t Get a Dog?

Should I Keep Talking To Someone Who's In An Open Relationship?

Where's the Line Between Being Shady and Wanting Privacy?

Is It Ever Too Early To Tell a Guy You’re Really Into Him?

Is It Time to Start Accepting That Closure Isn’t A Real Thing?

Is It Possible To Wait Too Long To Have Sex With Someone?

Can I Improve My Dating Life By Moving to a New City?

Is It Worse To Do The Slow Fade Or Ghost Someone Completely?

Should I Stop Seeing A Guy That Won’t Call Me His Girlfriend?

How Do I Get My Boyfriend To Talk About His Erectile Dysfunction?

Is It Fair To Judge My Partner For Not Being Ambitious Enough?

What's the Best Way to Handle Rejection?

Should We Stop Asking People What They’re “Looking For” On A Dating App?

Should I Reach Back Out To Someone Who Ghosted Me?

Can You Ask Someone To Delete Your Nudes After You Break Up?

How Detailed Should A Breakup Text Be After Just A Few Dates?

Can You Ever Assume You’re In A Relationship With Someone Without Having “The Talk”?

How Do I Get My Boyfriend To Spend More Time With Me? Ft. Dr. Naomi Bernstein (Jordana’s Sister)

Why Does He Keep Texting Me If He Won’t Make A Date?

How Do You Signal To A Guy That It’s Okay To Approach You In Public? Ft. Girls Gotta Eat

Is It A Red Flag If Someone Expresses Strong Feelings Right Away?

The One Where We Talk About Indian Matchmaking Ft. Aparna Shewakramani

Should I Be Worried That My Boyfriend Won’t Talk About Marriage?

Is It Normal To Obsess Over My Boyfriend’s Ex?

How To Interpret An Ex's Viewing Of Your Instagram Stories

Do You Deserve An Explanation If Someone Ends Things After the Third Date?

Is It Possible To Go From Sexting To Dating?

The One Where Jordana Got Engaged

Why Do People Keep Cancelling On Me Before Dates?

Is It Okay To Be Jealous Of My Boyfriend’s Hot Female Friend?

How to Judge a Guy By His Birthday Text

Why Are Some People Always In Relationships And Others Always Single?

How Do I Get My Partner To Compliment Me More?

Should I Respond To A Random Text From An Ex?

How Do I Get My Partner To Improve Without Insulting Them?

Why Was My Ex Able To Move On So Fast And I Can’t?

Is It A Huge Mistake To Tell A Guy That You’re Open To Something Casual?

Is It Okay To Ask Your Quarantine Fling Not To Hook Up With Others?

Is This Relationship Real Or Just A Quarantine Distraction?

Is It Okay To Like Photos Of Your Friend’s Ex?

Should Couples Stop Moving In Together Before Getting Engaged?

Who Gets To Decide Where You Quarantine As A Couple? Ft. Mark Manson

How To Tell If You’re Bored In Your Relationship Or Just Bored Of Quarantine

What Do You Do When You’re Fed Up With Quarantine Dating?

This Is What It’s Like To Quarantine In A New Relationship Ft. Sam Morril & Taylor Tomlinson

Are You Willing To Go On A FaceTime First Date? Ft. Nicole Byer

How Do I Know If My Partner Is Ready To Move In With Me?

How To Admit That Your Toxic Hookup Is Never Going To Change

Love In The Time Of Corona

How Many Times Should I Let Him Reschedule?

U Update: He Wouldn't Call Me His Girlfriend

The One Where We Talk About Love is Blind

How Do I Turn My Work Hookup Into A Real Relationship?

Am I Allowed To Be Upset With My Partner About What They Did Before We Were Exclusive?

Should You Expect A Valentine’s Day Date After A Month Of Dating?

When Is It Time To Admit Your Long Distance Relationship Isn’t Working?

Should I Come Clean About My Past On A First Date? Ft. Jordana’s Sister

Is It A Bad Sign If My Partner Still Talks About Their Ex? Ft. Luann de Lesseps

Why Do So Many Daters End Things At The Three Month Mark?

What Should You Do If You Find Out Your Partner Cheated On Their Ex?

How Do I Break The Cycle of Hooking Up With a Guy Who Won’t Date Me?

How Do I Handle A Guy Who Tries to Make It Too Sexual Too Fast?

Is It Important To Show Off The Person You’re Dating On Social Media?

When Is The Right Time To Unfollow An Old Hookup?

What Do I Do When My Partner Sucks At Buying Gifts?

How Soon Can You Start Dating After A Breakup?

Can You Ever Really Be Friends With An Ex?

How Do I Avoid Being The Drunkest Person In The Room?

How Do I Find Closure After An Unexpected Breakup?

If A Guy Likes My Instagram, Does That Mean He Likes Me?

Is It A Mistake To Follow Someone To Another City Just For Love?

How Often Do I Need To Text My Significant Other While I’m Away?

Would You Swipe Right On Someone From NSYNC? Ft. Joey Fatone

What’s the Best Way To Decline a Request For Nudes?

The Easiest Way To Get From A Dating App Convo To a First Date

Do I Get To Care About Who My Partner Used To Sleep With?

Is It Shallow To Only Want To Date Rich People?

How Do I Confront My Partner About Their Terrible Texting? Ft. Jonathan Van Ness

What’s the Best Way To Be Broken Up With?

Why Are Guys So Afraid Of Commitment?

What Counts As An Appropriate First Date Location?

How Do I Bring Up Weird Instagram Activity Without Sounding Crazy?

Should I Delete My Instagram Photos With My Ex? Ft. Rachel Lindsay & Travis Mills

How Many Dates Should It Take To Decide if You Have Sexual Chemistry With Someone?

Is It Hot Or Offensive To Leave Right After A Hookup? Ft. Tyler Cameron

How Do I Slide Into A Guy’s DMs Without Seeming Desperate?

How Do I Handle The Guy Who Wants To Take Things Slow?

Does It Count As Cheating If Your Partner Pays Strangers For Nudes?

Is It Better To Be The Dumper Or The Dumpee?

Who Should Pay For The Couples Vacation? Ft. Maddie Poppe

Is It A Deal Breaker If Someone Late Cancels A Date?

How to Stop Comparing Your Relationship to Everyone Else's

Is It Ever Okay To Question The Sexuality of the Person You're Dating?

What’s Worse, Looking Jealous or Crazy?

What Percent Of The Time Should You Expect To Be Happy In A Relationship?

Should I Put My Instagram Handle In My Dating App Profile?

Am I Being Ghosted Or Did The Conversation Just End?

When Is The Right Time To Ask If Someone Is Looking For A Relationship?

Are You Obligated To Reveal Your Phone Passcode In A Relationship? Ft. Dr. Helen Fisher

What’s The Difference Between Sexual Preference And Sexual Racism? Ft. Ronny Chieng

Can A Relationship Survive A Huge Body Transformation?

When Is The Right Time To Ask Someone To Move In Together?

How Do I Show Guys On Dating Apps That I'm Not Only Interested In Hooking Up?

Is Jealousy In A Relationship Flattering Or Annoying? Ft. Vinny Guadagnino

How Do We Ask Our Partners For More Sex?

Is It Tacky To Talk About Money With The Person You’re Dating?

How To Stop Sleeping With Someone Who Doesn't Want To Date You

Is Refusing to Define The Relationship A Dealbreaker? Ft Nev Schulman & Laura Perlongo

What To Do When He Can't Get It Up

How Do I Say "I Love You" First?

How Do I Hit On A Guy At The Gym?

How Many Dates Should You Wait Before Sleeping With Someone?

What Do We Owe An Ex After a Breakup?

Bonus UUP?: Live At Murmrr Theatre

How Do I Wear Lingerie Without Looking Stupid?

Bonus U UP?: Live At Underground Arts

How Long Into Dating Someone Should You Expect To Have Valentine's Day Plans?

Bonus U Up?: Live At Sixth & I

Were Jim and Pam Assholes or the Best Couple Ever?

What To Do When You're Blindsided By A Breakup

How to Date as A Single Parent Ft. Chris Distefano

How to Get A Guy To Go Down On You Ft. Violet Benson of Daddy Issues

Does The Person I’m Dating Care About My Instagram Brand?

Should You Be Mad If Someone You're Seeing Is Still Updating Their Dating App Bio?

Did Carrie And Big Have An Abusive Relationship?

Why are Millennials Having Less Sex than Our Parents' Generation? Ft. Kate Julian

What's The Best Way to Tell My Significant Other That They’re Getting Fat?

Were Ross and Rachel On A Break?

Is It Too Soon To Take A Trip With My BF?

Why Aren’t Stable Relationships Sexy?

Are Dating Apps Bad For Society? Featuring Nancy Jo Sales

Is Halloween the Best or Worst Hook-Up Night?

What Do I Do If My Significant Other Is Texting Their Ex? Ft. Johnny Bananas

How Do I Make the First Move Without Coming Off Desperate?

Bonus U Up?: Live At Canton Hall Ft. Raven Gates

What’s The Difference Between Loving Someone and Being “In Love?”

How Do I Stop My Boyfriend From Acting Like a Drunk Asshole? Ft. Girls Gotta Eat

What’s The Best Way to Get Someone to Stop Texting You?

Did Instagram Ruin My Relationship? Ft. Corinne Fisher

Bonus: U Up? Live At The Comedy Cellar (10 PM Show) Ft. Michelle Wolf

When Do You Introduce Your S/O To Your Friends?

Bonus: U Up? Live At The Comedy Cellar (8 PM Show) Ft. Matteo Lane

Is It Crazy to Call Someone Out After Stalking Their Instagram Story?

How to Know You're Chasing The Wrong People

Is a Cheap Guy a Dealbreaker?

To Text or Not To Double Text

Should I Swipe Right on Someone I Know IRL?

Can I Go Through My S/O's Texts?

Why Do Guys Stop Putting Effort Into Long Term Relationships? Ft. Hinge Founder Justin McLeod

Why Do Guys Really Send Dick Pics?

Bonus: U Up? Live at the Comedy Cellar (10PM Show) Ft. Liza Treyger

What's The Ideal Day of the Week for a First Date?

Do You Have To Break Up If They're Not The One?

Bonus: U Up? Live at the Comedy Cellar Ft. Andi Dorfman

Should You Tell Your Partner About A Time You “Almost” Cheated?

How Important Is It That Your Significant Other Likes Your Family?

Can You Start a Real Relationship From an Instagram Thirst Trap?

When's The Right Time To Talk About Your Sexual History? Feat. Taylor Strecker

Once a Cheater Always a Cheater?

Is It OK to Ask How Many People They’ve Slept With? Feat. Andy Cohen

How Do You Handle The First Fart In a Relationship? (Ft. Jax Taylor)

How Long Should I Put Up With a Guy Texting Me Without Asking Me Out?

How Do You Extend a Vacation Hook-Up?

What Do I Get a Guy For His Birthday If We've Only Been Dating a Month?

The Reason Guys Don’t Make Plans in Advance

What's The Proper Post Breakup Protocol?

How Do I Tell Someone I'm Seeing That I'm a Virgin

How Soon Should I Get Back on Dating Apps After a Breakup? Ft. Hannah Bronfman

Should I Hide the Fact That I Smoke Weed on a Dating App?

Is It Messed Up That My Boyfriend Goes to Strip Clubs?

What Do Guys Really Think of Fake Boobs?

How Many Dates Should You Wait Before Adding Someone On Instagram?

How to Plan a Date Without Looking Desperate

Stop Instagram Stalking Your Exes with Whitney Cummings

Do Women Have More to Gain From Marriage Than Men?

Is It OK to Talk About Your Ex?

How Much Porn is Too Much Porn?

If You’re Not On His Instagram It’s Not Official

How Many Drinks Should I Have On A Date?

What’s The Best Way To Dump Someone?

Should You Have ‘The Talk’? The Great Debate

Blowjobs Are a Selfless Act

Don’t Text for A Specific Response

Girls Trying Not To Be Crazy Is What’s Gotten Guys Laid for Centuries

Is it ever okay to fake an orgasm?

You're Not Better Than The App

Why Does My Boyfriend Rarely Seek Out Sex?