People write in to ASK MIDLIFE BACHELOR with many types of questions.  Email your questions to us in complete confidence at [email protected].


My Girlfriend Says I Drink Too Much
Should Rebound Bachelor Marry Rich Woman?
Date Someone Separated but Not Divorced?
Girlfriend Pregnant in her Forties
Moving Too Fast in a New Relationship
No Luck Online Dating?
How Much Sex is Normal at Midlife?
Cheap Date – Is He Too Cheap to Keep?
He is Unapologetic about his Relationships with his Ex’s
How Long to Wait to Have Sex?
I Could Not Sleep with the Fat Woman
Boyfriend’s Female Friends are Making Me Crazy
Pregnant Online Date Harrassing Me
Should I Date a Fat Woman?
Online Date Disappears for Weeks at a Time
Needy Woman is Driving Me Nuts
Move On Immediately when Relationship Fizzles
Dating Down Brings Disappointments
Time to Cut Boozer Boyfriend Loose
How to Date a Rich Man or Woman
Relationships Based Only on Lust Often Fail
Rich Man Talks Filthy on First Date
She Wants to Date Mr. Low Self-Esteem
When to Take Down Your Online Dating Profile?
Online Dates Want to Jump into Bed?
Difficulty Dating After Divorce
Rebound Relationships Often Do Not Last
Give Hot-and-Cold Psycho Girlfriend the Boot
You are a Back Burner Boyfriend
Rich Midlife Bachelor Cannot Find Love
Lack of Contact after a Great Date
Should She Get Breast Implants at Midlife?
Dealing with a Marriage Ultimatum
End the “Break Up” then “Get Back Together” Cycle
Dating Someone Married – Like Rielle Hunter Did w/John Edwards
How to Get Past Her Playing HARD TO GET
How Soon is Too Soon to Have Sex?
Difficulties Dating a Cancer Survivor
Her Best Friend Used Her
Mid 40s Boyfriend Too Cheap for Mid 20s Model Girlfriend
Mid 40s Man Won’t Commit
No Date on Valentine’s Day?
New Jealous Girlfriend Turns Psycho
Rebound Bachelor Wants to Marry Again
Sincere Religious Man Chases Widow
New Midlife Boyfriend is Flaccid
Tramp Wife Calls Cops on Husband
You Cannot Force Someone to Love You
Giant Man Hasn’t Had a Girlfriend in 10 Years
Man Allows Ex-Wife to Steal his Self-Respect
Tall Woman Wants to Cross the Friendship Line
Dumped Over Email after 5 Year Relationship
When / How Often to Contact a New Date?
He Won’t Call Me Back – What to Do?
Should I Keep My Odd-Looking Short-Bus Boyfriend?
Man Wants Girlfriend 20+ Years Younger (don’t we all?)
Cannot Get into Platonic Room-mate’s Pants
New Girlfriend Too Hairy Down There
Older Bachelor Needs a Cougar
Hottie Needs to Put Moves on Shy Professional
Psycho STD Scare?
Best Friend Hitting On My Tramp Wife
Should I Have Sex with My Ex?
Older Man Worries Younger Girlfriend Will Stray
When / How to Contact a Blind Date
The Unintentional Tease
Stick with a Long Distance Relationship?
Should High Income Woman Risk Friendship by Dating the Handyman?
Stalker Ex Drives Woman Crazy
Dating Challenges of a High Income Woman
Age 52 and Still a Virgin
Midlife Crisis of Confidence
Mr. Never Married at Midlife
The 30’s Life Crisis
Dumped – Sudden Change Syndrome
Dump the Date You Never See
The “Friends with Benefits” Landmine
No Second Date
Break Out of the JUST FRIENDS Rut
Is He Just Not that Into Me?
Best Way to Dump a Nice Girl?
Some Women Have a Sense of Entitlement
Female Friends – When to GO FOR IT?
Cannot Keep a Girlfriend Very Long
Go for It or Risk Just Being Her Friend
40 Years Old and Cannot Get a Date
Girlfriend Jumps Out of Car at Stoplight – Good or Bad?
51-Year Old Hot Latina Wants Younger Man
Having Time to Spend with a Woman is a Key Advantage
Younger Man / Older Woman
Older Man / Much Younger Woman – YES!

Have you suddenly found yourself single again after having been previously imprisoned in a long-term relationship (ha ha)?  If so, then be sure to check out the sections here on:

Fundamental Truths about Women and Midlife Dating Today
Midlife Bachelor Personal Makeover
Develop a Strategy for Midlife Bachelor Success
Reaching Midlife Bachelor Personal Equilibrium

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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.