All Episodes

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