All Episodes

Dear Rollie D: I Keep Waiting For A Special Occasion That Never Comes To Use My Household Items

Dear Rollie D: I Keep Buying Expensive Items For Hobbies Then Not Using Them

Dear Rollie D: I Feel A Need To Excel At All My Hobbies & It's Driving Me Nuts

Dear Rollie D: My Co-Worker Is ALWAYS One-Upping Me

Dear Rollie D: I Make Commitments With Friends Then Don't Want To Keep Them

Dear Rollie D: I'm Always the Initiator of Plans In My Friend Group

Dear Rollie D: I'm Tired Of My Kids Playing "Good Cop, Bad Cop" With My Partner & I

Dear Rollie D: I'm the Last Friend Living In My Hometown

Dear Rollie D: I'm Tired of Being the 3rd Wheel

Dear Rollie D: I'm Living With A Human Tornado

Dear Rollie D: My Friend Only Comes To Me When They Need Something

Dear Rollie D: My Partner Feels Like A Stranger After A Busy Summer

Dear Rollie D: I'm Already Mentally Winding Down From Summer

Dear Rollie D: I'm Struggling With How To Best Use My Vacation

Dear Rollie D: I'm Always the Driver & I'm Tired of It

Dear Rollie D: My 15 Year Old Is Growing Distant

Dear Rollie D: My Boyfriend Is Great, But He Hangs Out With A Female Best Friend

Dear Rollie D: I've Fallen In Love With My Best Friend

Dear Rollie D: I'm Overwhelmed w/ Being My Family's "Fixer"

Dear Rollie D: I Struggle To Finish A Book

Dear Rollie D: My Dad Wants To Go Fishing Every Weekend

Dear Rollie D: I'm Tired of Being the Point Person for Family Gatherings

Dear Rollie D: I've Fallen Into A Nostalgia Trap

Dear Rollie D: I'm Suffering From Post-Vacation Blues

Dear Rollie D: Did I Bite Off More Than I Can Chew With My Purchase Of A Home?

Dear Rollie D: My Collection of Personal Stuff Is Too Large

Dear Rollie D: I've Over Volunteered My Time And Feel Guilty Letting It Go

Dear Rollie D: I'm Losing Touch with My Close Girlfriends

Dear Rollie D: I Haven't Been Doing Well With My Resolutions

Dear Rollie D: I Enjoy Being A Hermit... Is That Bad?

Dear Rollie D: I'm Feeling Overwhelmed By All the Wedding Invites I'm Getting

Dear Rollie D: Help! I Swiped Right On Someone I Know On Tinder!

Dear Rollie D: My Parents Need A Crushing Amount of Help with Technology

Dear Rollie D: My Summer Sleep Is Suffering

Dear Rollie D: My In-Laws Keep Showing Up Without Notice

Dear Rollie D: My Car Is Getting Older

Dear Rollie D: I'm Tired of Always Being the Reliable Friend

Dear Rollie D: My Kids Are Getting Restless On Summer Break

Dear Rollie D: My Summer Body Hasn't Arrived

Dear Rollie D: I Caught Feelings For Someone Who's Only Here For Summer

Dear Rollie D: My Summer Weekends Feel Too Full

Dear Rollie D: I'm 24 and Feeling Stuck

Dear Rollie D: I'm Worried My Hobbies Are Embarrassing

Dear Rollie D: I'm Slacking At Work Due to the Sun

Dear Rollie D: I Feel Like A Zombie After Long Weekends

Dear Rollie D: My Fix-It List Is Overwhelming Me

Dear Rollie D: I Feel Like An Impostor At Work

Dear Rollie D: I'm Dreading A Visit From My Parents

Dear Rollie D: My Money Keeps Disappearing

Dear Rollie D: My Girlfriend Might Not Be Ready For What I'm Ready For

Dear Rollie D: My Kids Are Having A Meltdown Waiting for Summer

Dear Rollie D: I'm Struggling With My Husband's Camping Itinerary

Dear Rollie D: I've Overbooked My Schedule

Dear Rollie D: My Brother Won't Stop Asking For Money

Dear Rollie D: My Plants Are Dying!

Dear Rollie D: My Friend Cancels On Plans Last-Minute

Dear Rollie D: I've Almost Succeeded With A Big Goal

Dear Rollie D: My Boyfriend Makes Me Feel Small

Dear Rollie D: My Boyfriend Still Texts His Ex

Dear Rollie D: I Feel Overly Criticized By My Wife

Dear Rollie D: Life Feels Mundane w/ My Partner

Dear Rollie D: I'm Having Issues With My Neighbor

Dear Rollie D: My Kids Always Want To Be Outside

Dear Rollie D: I'm Having A Quarter-Life Crisis

Dear Rollie D: My Diet Isn't Working Out

Dear Rollie D: I'm A Burnt Out Yes Man

Dear Rollie D: My Co-Workers Push Boundaries

Dear Rollie D: I Want To Be Considerate with My Pranks on April Fool's Day

Dear Rollie D: I Got Too Ambitious with My Spring Cleaning

Dear Rollie D: I'm Too Stressed To Doodle

Dear Rollie D: My Son Is A Phone Zombie

Dear Rollie D: Should I Get A Puppy?

Dear Rollie D: I'm Overwhelmed By the Arrival of Spring

Dear Rollie D: I Got Too Drunk On St. Patrick's Day

Dear Rollie D: My Job Has Lost Its' Spark

Dear Rollie D: It's Time To Get My Act Together

Dear Rollie D: It's Friday the 13th and I'm Dreading It

Dear Rollie D: My Fifteen Year Old Is Testing Limits

Dear Rollie D: There's A Barista....

Dear Rollie D: My Close Friend Is Single

Dear Rollie D: My Ten Year Old Son Is A Handful

Dear Rollie D: My Wife & I Are Having A Tough Winter

Dear Rollie D: February's Dragging On Forever & I'm Feeling Flat

Dear Rollie D: Remote Work Is Taking A Toll

Dear Rollie D: Valentine's Day Disappointment

Dear Rollie D: I Need To Set Boundaries With My Parents

Dear Rollie D: My Friend's A "Negative Nelly"

Dear Rollie D: My Boyfriend Leaves His Dirty Socks Everywhere

Dear Rollie D: My Girlfriend Is Dropping Hints About Valentine's Day

Dear Rollie D: My Boyfriend Always Orders For Both of Us