The Dating College · Course

Dating Over 40 (and 50, and 60)

Build a dating life that fits who you are now: an honest profile, a real plan, conversations worth having, and room for two full lives. Practical lessons for dating after 40, 50 or 60.

For adults dating after 40, 50 or 60, including after divorce, widowhood or a long relationship, or coming out later in life. No prior course required.

Start level 1 free

Milo and Mia in their early fifties, greying at the temples, chatting in an art gallery.

Your hosts: Milo & MiaThey open the course and turn up along the way, with a few of their friends. Meet them →

The seven levels

21 short courses in 7 levels. Each course has 5 lessons and an exam of 7 or 8 questions (pass with 80%). Retakes are included.

I NewbieBack on the market, with better judgment. Free

The Profile, Revised EditionPhotos From This Decade · The Back Story, Abridged · A Full Life, Not a Scheduling Problem · Low Patience, High Clarity · A Bio That Sounds Like You
Ready, or Just Restless?Ready, or Just Lonely on a Sunday? · Dating After Loss · After the Divorce (or the Long Relationship) · First Time, Later Than Most · Your Patterns, Gently Audited
The Apps Have Changed (and So Have You)Where Grown-Ups Meet Now · Swipe Literacy · The Age Filter, Honestly · The Opening Line, Grown-Up Version · From Chat to Coffee

II ApprenticeThe first date, done properly.

Dressed for the Life You Have NowFit Is the Real Fountain of Youth · Neither 1998 Nor the Fleece · Grooming, Updated · Shoes for Walking Dates · Reading Glasses Are Not a Confession
The First Date, Planned by Someone Who's Done This BeforeThe Invitation · The Daytime Date Advantage · The Venue Test, Revised · Logistics When You Have Dependents · Ending on Time Without Ending Badly
Safety Doesn't RetireTell Someone · The Video Call Check · Romance Scams: The Script · Money Requests Are Exits · Trust the Uneasy Feeling (and Be the Safe Date)

III PractitionerBe interesting. Be interested.

Conversation Without the RésuméThe Follow-Up Question · Share, Then Ask · Topics That Work After 40 · The Organ Recital · Humor, Kindly
Talking About Your Past Without Reliving ItThe Ex Question · Kids, Briefly · Career Highs Without the Lecture · Vulnerability, Measured · Notice Their Signals
The Bill, the Goodbye and the Follow-UpThe Bill, Without the Standoff · Manners Are Still Watched · The Goodbye · The Follow-Up, No Games · Not Interested? Say So Kindly

IV SpecialistSecond dates and second chances.

Texting at Your Own PaceThe Rhythm · Phone Calls Are Allowed Again · Tone Doesn't Travel · Emoji Diplomacy · Plans, Not Pen Pals
The Second Date, and the ThirdRemember the Details · Do Something Together · Show Them a Piece of Your Real Life · Let Them Plan One · Read the Momentum
Rejection, With the Benefit of ExperienceGetting Turned Down · No Means Done · Turning Someone Down Kindly · Ghosting Is Beneath You · Bouncing Back

V ExpertChemistry, consent and the body you actually have.

Chemistry, With ConsentChemistry Is Mutual · Asking Is Still Attractive · Pace Is Personal · Changing Your Mind Is Allowed · Sober Signals
Confidence in the Body You HaveAttraction Doesn't Retire · Scars, Surgeries and Stories · Health Disclosure: What and When · Intimacy After a Long Gap · Sexual Health Isn't Just for the Young
Red Flags, Green Flags and Beige FlagsRed Flags · Green Flags · Beige Flags · Love-Bombing and the Fast-Forward · Trust Your People

VI Distinguished FellowTwo full lives, one relationship.

"So… What Are We?" at Fifty-SomethingTiming the Talk · Labels for Grown-Ups · Exclusive, or Not Yet · Living Apart Together · Going Public
Kids, Grandkids and ExesTelling the Kids · When to Introduce Them · Adult Children Have Opinions · Grandkids, Holidays and Calendars · Exes Who Are Still in the Picture
Money, Grown-Up EditionDifferent Incomes, Same Evening · Who Pays, Revisited · Money Values Show Early · Never Lend What You Can't Lose · Protecting What You've Built

VII MasterA practice, not a finish line.

The Big Conversations, Later in LifeWhere Do We Want to Be in Ten Years? · Retirement Dreams, Compared · Health, Caregiving and the What-Ifs · To Move In, or Not · Asking Without Pressure
Blending LivesTwo Households, Two Sets of Habits · Merging Families Gently · Friends From Before · Traditions, Old and New · Your First Real Disagreement
Master of Grown-Up RomanceKeep Dating After You're Dating · Small Things, Often · Keep Becoming Yourself · Check In · Graduation