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Protecting Your Balls

Take it from Evan Jacobs: wear compression shorts. You don’t want to go where he’s been. I am a hypochondriac. I always have been, always will be. On the other hand, I have many legitimate problems....

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The Prostitute Who (Almost) Saved My Relationship

VirtualTourist A few weeks into a relationship, Evan Jacobs was obsessed. Not with his new girlfriend—with his plan to pay for sex in Amsterdam. I met my ex-girlfriend by replying unironically to an...

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My Dad, the UFO Expert

Fourth grade isn’t exactly a walk in the park, but for Evan Jacobs, having a dad who knew a lot about space aliens was the ticket to social acceptance. It’s been mostly downhill from there. ♦♦♦ My...

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Chronicles of a Phone Sex Addict, Part I

Image via thedailyaffair.com Evan Jacobs’ first love was the voice of a girl he’d never met. Thousands of dollars and hours of therapy later, he’s still coming to terms with his phone-sex addiction. To...

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How to Date Your Ex’s Best Friend

‘The ideal Evan Jacobs—the brash, confident stud I still want to be—existed for nine months of my sophomore year at the University of Chicago.’ It’s hard to go through life without regrets. Sometimes...

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Chronicles of a Phone Sex Addict, Part II

In college, Evan Jacobs—the ‘saddest egotist of all time’—stole his mother’s work phone and retreated to the seedy world of phone-sex party lines. His mom nearly lost her job. Evan got a shrink. Hi....

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My Hemorrhoids Make Dating Pretty Awkward

You are about to read the most entertaining story you’ve ever read about hemorrhoids. “This is my finger,” says Dr. Brandeis. I ask him, giggling, if he’s at least going to take me to dinner first....

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Humor Lessons From a Third-Rate Comedian

Walking embarrassment Evan Jacobs tells you everything you need to know to alienate friends and irritate people. How to be funny? There is no one less qualified to give out this information. I am not...

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How to Lose a Girl in 10 Semesters

Evan Jacobs recalls the one that got away, and how he let her go. To me, she was Becky. To anyone else: Rebecca. I met her my on first day of college. I turned down a dorm hallway, and there she was,...

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Image may be NSFW.
Clik here to view.

Protecting Your Balls

Take it from Evan Jacobs: wear compression shorts. You don’t want to go where he’s been.I am a hypochondriac. I always have been, always will be. On the other hand, I have many legitimate problems. As...

View Article

Image may be NSFW.
Clik here to view.

The Prostitute Who (Almost) Saved My Relationship

VirtualTouristA few weeks into a relationship, Evan Jacobs was obsessed. Not with his new girlfriend—with his plan to pay for sex in Amsterdam.I met my ex-girlfriend by replying unironically to an...

View Article

Image may be NSFW.
Clik here to view.

Chronicles of a Phone Sex Addict, Part I

Image via thedailyaffair.comEvan Jacobs’ first love was the voice of a girl he’d never met. Thousands of dollars and hours of therapy later, he’s still coming to terms with his phone-sex addiction.To...

View Article

Image may be NSFW.
Clik here to view.

Chronicles of a Phone Sex Addict, Part II

In college, Evan Jacobs—the ‘saddest egotist of all time’—stole his mother’s work phone and retreated to the seedy world of phone-sex party lines. His mom nearly lost her job. Evan got a shrink.Hi. Uh...

View Article


Image may be NSFW.
Clik here to view.

My Hemorrhoids Make Dating Pretty Awkward

You are about to read the most entertaining story you’ve ever read about hemorrhoids.“This is my finger,” says Dr. Brandeis.I ask him, giggling, if he’s at least going to take me to dinner first. And...

View Article

Image may be NSFW.
Clik here to view.

How to Lose a Girl in 10 Semesters

Evan Jacobs recalls the one that got away, and how he let her go.To me, she was Becky. To anyone else: Rebecca. I met her my on first day of college. I turned down a dorm hallway, and there she was,...

View Article


Image may be NSFW.
Clik here to view.

Humor Lessons From a Third-Rate Comedian

Walking embarrassment Evan Jacobs tells you everything you need to know to alienate friends and irritate people.—-How to be funny? There is no one less qualified to give out this information. I am not...

View Article

Image may be NSFW.
Clik here to view.

How to Date Your Ex’s Best Friend

‘The ideal Evan Jacobs—the brash, confident stud I still want to be—existed for nine months of my sophomore year at the University of Chicago.’It’s hard to go through life without regrets. Sometimes a...

View Article


Image may be NSFW.
Clik here to view.

My Dad, the UFO Expert

Fourth grade isn’t exactly a walk in the park, but for Evan Jacobs, having a dad who knew a lot about space aliens was the ticket to social acceptance. It’s been mostly downhill from there. ♦♦♦My...

View Article
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