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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.

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 […]
applying your cologne men
Ask Jack

Should I Put On Cologne Before Sex?

Jack Heart
When you are thinking of spraying on cologne before intimacy HIS QUESTION Dear Jack, I’ve got a question that might strike you as odd. Do you think it is OK to put on cologne before […]
hypnosis forget someone
Ask Jack

Can Hypnosis to Forget Someone After Breaking Up Work?

Jack Heart
Does hypnosis to get over your ex work? HIS QUESTION Dear Jack, Recently, I broke up with a person I dated for a year and am having a hard time getting over the relationship. I […]
ashamed of size
Ask Jack

I’m Ashamed of My Equipment Size and It’s Ruining My Love Life

Jack Heart
When you are embarrassed about your equipment size HIS QUESTION Dear Jack, It’s taken me a long time to write this note because it’s so embarrassing. Perhaps the best way to do this is to […]
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 […]
condom cheating
Ask Jack

If She Insists on a Condom, Is That a Sign of Cheating?

Jack Heart
You are both exclusive, but she still wants you to wear a condom Jack offers answers to tough questions men want to know about love, romance, and relationships. His Question Hi, Jack, I’ve been dating […]
Libras - men in love
Ask Jack

What to Do If She Dumps You and Then Wants You Back

Jack Heart
She dumps you and now wants to get back together She’s gone forever…no wait, she’s back again. Your girlfriend dumped you, but now she wants you back. Is it time for a victory lap or […]
meeting parents over coffee
Ask Jack

Meeting Your Girlfriend’s Parents Do’s and Don’ts

Jack Heart
Meeting your girlfriend’s parents? Here’s some tips! “His palms are sweaty, knees weak, arms are heavy There’s vomit on his sweater already, mom’s spaghetti He’s nervous, but on the surface, he looks calm and ready” […]
men's cologne bottle
Ask Jack

Is Wearing Cologne on a First Date OK?

Jack Heart
When you aren’t sure if it’s OK to wear cologne. HIS QUESTION Hi, Jack, This may sound like a silly question but here it goes. I am wondering if it is OK to wear cologne […]
gemini man with a woman
Ask Jack

How To Approach a Woman You Don’t Know with Confidence

Jack Heart
Want her number? Here’s how to get it Struggling with how to approach a girl and ask for her number? Hoping to break the never-ending cycle of chickening out and regretting it later? Need some […]

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Check It Out

  • condom cheating
    If She Insists on a Condom, Is That a Sign of Cheating?
  • men's cologne bottle
    Is Wearing Cologne on a First Date OK?
  • girl social media
    What To Do When Your Girlfriend is Addicted To Social Media
  • Young man closely examining his face in a bathroom mirror while watching appearance-improvement content.
    I’m Caught Up in Looksmaxxing and I Can’t Get Out
  • applying your cologne men
    Should I Put On Cologne Before Sex?

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