A sunbathing nude neighbor, a friend snooping through pictures, and a daughter meeting her mother’s new boyfriend.
Dear John: Do I Really Want An ‘Escort’ For My 26th Birthday?
A 26-year-old virgin hiring an escort for his birthday, a boss feeling undermined, and the myth of the perfect male body.
Dear John: Remaining A Couple Will Require A Third Person
Time away from an ex who is sleeping with someone else, serial break ups, and a husband who is uninterested in sharing a social life.
Dear John: It Feels Too Right To Be Wrong
An Eleanor Roosevelt-type extramarital affair, pubic grooming, and a friend who loaned out the money they owed him.
Dear John: Pro Golfer Wants To Play Her
A chance to get with a pro-golfer who is married, a self-conscious man with gynecomastia, and keeping a daughter from her grandparents awful relationship habits.
Dear John: An Affair To Forget
A late discovery of an affair, a thankless favor, and a second breakup from wanting to get back with their ex.
Dear John: I Think My Boss Is Having An Affair
A boss who might be having an affair, a friend going crazy with tattoos, and neighbors who are suddenly dog-crazy.
Dear John: Boyfriend’s Sexy Talk A Total Turnoff
A guy saying suggestive things in front of her son, a coworker who got mailed pot, and a couple on opposite ends of the political spectrum.
Dear John: He Thinks It’s Hot, I Think It’s Not
A boyfriend’s lovemaking preferences, a roommate who drops into events without invitation, and exercise getting in the way of the marriage.
Dear John: Getting Girlfriend’s Son Off The Couch
A sedentary son, a boyfriend planning an unpleasant vacation, and girlfriend who hangs up.
Dear John: He Says I Cry Too Much
A boyfriend who thinks his girlfriend cries too much, a guy who thinks his gay friends have too much PDA, and a son playing violent video games at a friends house.
Dear John: With His Father Dying, So Are His Chances To Talk
A last chance for a son to reconcile with his dying father, a father pushing his son to be involved in aggressive sports, and a boyfriend who was abused as a child.
Dear John: My Womanizing Roommate Is After a Girl I Like
A flirty roommate, a disappointed friend after a job opportunity doesn’t pan out, and a mom who doesn’t want her son to study abroad.
Dear John: Should She Leave Her Son With Her Boyfriend?
Questions about her babysitting choices, a boyfriend with an atrocious apartment, and a step-father selling off the mother’s prized possessions after her death.
Dear John: My Co-Worker Makes Me Feel Dirty
A germaphobe coworker, a boyfriend who used to see escorts, and a regretful past of bullying.
Dear John: Are Her Feelings More Important Than The Mortgage?
An unreasonable spouse over insurance, missing information about a sister, and a broken ankle on a neighbor’s icy porch.