All episodes
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