An irritating accent, a coworker constantly staring at cleavage, and a confusion about a friend’s expectations.
Dear John: Will Boyfriend’s Solitary Pleasures Lead To Pain?
Masturbation getting in the way of their sex life, a kissy aunt with cold sores, and parents trying to fight princess culture.
Dear John: Haunted By Hook-Up At His Kid’s School’s Drop-Off
Someone bound to remember a regrettable hook-up, a friend who can’t take criticism, and an ill friend who guilts people into getting what she wants.
Dear John: Deathbed Confession Is Good For Whom, Exactly?
A deathbed confession of a stolen ring, gun-proofing a son’s sleepovers, and a badmouthing ex-wife.
Dear John: Should She Be His Sugar-Mama?
A woman making more money than her boyfriend, photoshopping friends’ faces into compromising photos, and a lonely fifth wheel.
Dear John: A Guest Who Brings a Lot of Baggage
An old secret threatens a marriage, a girlfriend won’t open up about changes in her life, and a father of three suddenly wants a motorcycle.
Dear John: Dad Wants to GPS-Stalk His Teen Daughter
Stalker dad, a troubled marriage considers swinging, and an old friend of a spouse reappears, to the letter writer’s dismay.
Dear John: He’s Not Homophobic; He’s Boring-Phobic
Dear John talks about a gay friend, a boyfriend who flees the bed after sex, and a gender-bending boy spending vacation with grandpa.
The Best of Dear John from 2012
Read the best answers by Dear John about sex, relationships, dating, kids, affairs, and more.
Dear John: Cheapskate Dates
Dear John advises on cheap dates, taped sex without consent, and a friend torn between religion and honesty.
Dear John: She Doesn’t Want Him …Until She Can’t Have Him
Dear John addresses a repetitive heart breaker, ripped gifts, and a friend spouting personal information.
Dear John: My Neighbor Is A Pervert
Dear John addresses a guy next door watching porn, a girlfriend posing nude for art school, and a passive-aggressive neighbor.
Dear John: Going From One Bad Relationship To Another
Dear John addresses a bad rebound, a friend who wants a pot-head to get a “real job”, and a cute landlord.
Dear John: Haunted By A Hook-Up
Dear John addresses a bisexual hook-up from the past, a jealous coworker, and an anonymous note about body odor.
Dear John: Breaking Up Is Hard To Do (Like, Really Hard)
Dear John addresses an unclear breakup, contacting a stranger on a train, and fighting in front of kids.
Dear John: He Wants His Space … After Three Years
Dear John gives advice about a suddenly distant boyfriend, a guy who dresses below his age, and friends bashing a son’s career choice.