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Ask Jack

Ask Jack offers straightforward, thoughtful advice for men navigating relationships, confidence, sex, work, identity, and the complicated situations life throws their way. Real questions. Honest answers. No judgment.

couple intimacy communications
Ask Jack

How To End an Extramarital Affair with a Coworker

Jack Heart
You’ve been having an extramarital affair a coworker HIS QUESTION Dear Jack, I never thought I would admit this but here it goes. I’ve been having an extramarital affair with a coworker for the past […]
girl social media
Ask Jack

What To Do When Your Girlfriend is Addicted To Social Media

Jack Heart
What to do if your girlfriend is obsessed with social media His Question: Dear Jack, Let me start out by saying – my girlfriend is great. She’s smoking hot and she’s really down to earth […]
man feeling insecure about his size
Ask Jack

I’m Insecure About My Penis Size. What Do I Do?

Jack Heart
“IS THIS NORMAL, OR IS SOMETHING WRONG WITH ME?” HIS QUESTION Dear Jack, I’m embarrassed to even write this, but I’m insecure about my size. I’ve avoided dating, I compare myself to other guys, and […]
Young man closely examining his face in a bathroom mirror while watching appearance-improvement content.
Ask Jack

I’m Caught Up in Looksmaxxing and I Can’t Get Out

Jack Heart
Caught in the Looksmaxxing Trap? Dear Jack, About six months ago I started looksmaxxing. Skincare routine, gym consistency, better haircut, watched videos on posture and jawline stuff, even started tracking what I eat more carefully. […]
Man reflecting
Ask Jack

Should I Start an OnlyFans to Make Extra Money?

Jack Heart
Thinking of Starting an OnlyFans Account for Extra Money? His Question: Dear Jack, I’m behind on bills and I keep seeing people online talking about how much money they make on OnlyFans. It seems like […]
man in mirror with grooming tool for use with his genitals
Ask Jack

How to Shave Your Pubes Safely: A Guide for Men

Jack Heart
Affiliate Disclosure: Guy Counseling is a participant in the Amazon Services LLC Associates Program. Some links in this article are affiliate links, which means we may earn a small commission on qualifying purchases at no […]
no contactrule
Ask Jack

When Should I Use the No Contact Rule and For How Long?

Jack Heart
How the no contact rule benefits guys after a break up Are you thinking of employing the no contact rule after a breakup? Trying to weigh the pros and cons of taking such a drastic […]
Ask Jack

Can a Straight Guy Fall in Love with a Gay Man?

Jack Heart
Is it possible a straight guy can be attracted to the same sex? His Question Dear Jack, I’ve found myself in the oddest situation. I’m 31, married to a woman and have a child. For […]
man reading book depressed
Ask Jack

10 Great Novels You Should Read if You’re Feeling Depressed

Jack Heart
10 Books To Read When Depressed When you’re feeling a bit down in the dumps, a great story might offer some comfort and inspiration in trying times. There are plenty of self-help books out there […]
girlfriend cheats on you
Ask Jack

My Girlfriend Cheated On Me – What Should I Do?

Jack Heart
“MY GIRLFRIEND CHEATED ON ME – PLEASE HELP!” HIS QUESTION Dear Jack, Recently, I learned that my girlfriend cheated on me. To make a long story short, I found out after seeing her with another […]

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