He Had The Key To Her Heart, But Not Her Jail Cell



Last month, my friend Jill spent the night with the guy she was seeing, Kyle. There was only problem: His parents were extremely strict and she wasn’t actually allowed to be there.

They were planning on beating the system by waking up at 7AM, before his parents woke up. Naturally, they overslept.

At 9:30AM, Jill called our friend Marissa.

“Mariss, you have to come get me,” she frantically whispered. I’m hiding out in Kyle’s basement until his parents go out to breakfast.” Continue reading

Is That Your Thong Wrapped Around My Chihuahua’s Head?


BEVERLY HILLS CHIHUAHUA (2008)<br /><br /><br />
PIPER PERABO (left), CHLOE (right)My friend Marissa (the fake belly dancer) told me a hilarious story that reminded me of one of my favorite episodes of Frasier.

One morning, after spending the night with her boyfriend, she started getting dressed to go home. Unfortunately, she was missing something: her thong. She looked all over his room, and then eventually gave up and left the house commando.

Later that day, her boyfriend called her hysterically laughing. Continue reading

When Having Alley Sex With A Hooker, Always Be Sure To Look For A Five O’Clock Shadow


I have a bunch of friends that work in the sanitation department – and let me tell you…those guys have some stories.

One night at four in the morning, one of the guys, who I’ll call Lou, came across a hooker.

“For thirty bucks I’ll give you a blowjob,” she said.

“Frank, you gotta let me borrow thirty bucks,” Lou said to his coworker. “I promise I’ll finish the rest of the route.” Continue reading

When There’s Nothing But A Guitar Between You & Your Girlfriend’s Parents


photoMy friend Jack recently took up the guitar. One morning, he woke up at his girlfriend Lucy’s house and decided to sneak into the living room in his underwear to practice.
As he sat there playing a Greenday song, he heard the jingling of a lock. In walked Lucy’s parents, holding cleaning supplies and breakfast (their weekly tradition which he had completely forgotten about).
Shit, Jack thought. What am I gonna do now??



The following is a guest post from a JenAndMen reader (who I’ll call Frank). Frank emailed me at JenAndMen@hotmail.com to tell me about a time he was caught by an uncle of his girlfriend-at-the-time, while she was…well, while she was doing something that no one would ever want their uncle to see…

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Giving New Meaning To “A Balcony View”



Two of my good friends, Lucy and Jack, went on vacation to Aruba a few years ago. They had a beautiful room, but were a little annoyed that it wasn’t beachfront but, rather, on the third floor. Rather than let it ruin their trip, they decided to see the light in the situation — privacy.

One afternoon after going for a swim they decided to “consummate their love”. Anyway, after about a half hour, Jack saw something in the corner of his eye, which made both of them turn toward the window. Horrified, they came to a realization: Close the curtains even if your room isn’t on the ground level. Continue reading

Is It Weird To Sit Next To My Boyfriend At Restaurants?

As you already know, my boyfriend, Mark, and I are constantly disgusting those around us by canoodling, kissing, and gazing into each other’s eyes. I was hoping it would get better but I actually think it somehow got worse.

A few nights ago I met Mark in Manhattan for dinner at Tony Dinapoli’s. We sat across from each other and held hands under the table and played footsie over the table. Not too bad, right? Okay there may have been minor gazing. A few air kisses. And one real kiss when I got up because I couldn’t resist any longer. Alright we’re disgusting. I’ll pay the dry cleaning bill for the shirt you just vomited on.

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While On The Train: To Approach Or Not To Approach, That Is The Question


Only-in-New-York-1My friend Joe and I were discussing train flirting the other day. He had seen a really pretty girl on his way to work, and didn’t know if it was appropriate to say something to her.

While going back and forth about it, he came up with a really good line. If the girl got off at his stop, he’d say, “Listen, you really don’t have to stalk me. I’ll just give you my number, it’s okay.”

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Ever Notice The Person That Makes You Feel The Best Can Also Make You Feel The Worst?


If you’ve ever been in love — or at the very least happy with someone — you can attest to the fact that the person you’re with can affect your entire mood. A fight can make your day miserable and making up can chase that black cloud away immediately.

I guess the real question is, How can someone that makes you feel so great also make you feel so horrible? They can make you feel like you’ve finally got it right; you’re not alone, weird, destined to die by yourself. Then, in the drop of a hat, something they say can make you feel all those things ten-fold, because you thought you had found the person you were meant to be with, and now you’re second-guessing them, the relationship, and yourself.

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Guys, Just Look Pretty & Don’t Speak; I Like You Better When You’re Silent


Girls always get the bad rep of having big mouths, but I’ve come to realize over the past 10 years of dating that I like guys a lot more when they’re completely silent. I have yet to come across a guy that didn’t piss me off at least three times a day. And that’s seriously low-balling it.

It’s as if they go out of their way to piss me off, hurt my feelings, disgust me, or flat out repulse me. I only date good looking guys, so really if they just called, texted, and spoke less, I really feel like we’d have a better shot.

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I Sent A Guy A Text About Another Guy By Accident!


This is just sad on my part. I was once talking to my friend Chris about a guy I had been seeing a couple weeks prior. The conversation turned to whether or not he was a good kisser. I proceeded to go into detail about his terrible kissing skills. Then I looked up at the name on my iPhone screen.

It. Wasn’t. Chris’.

I realized that I had been sending these texts to a new guy, David, I was talking to! FML isn’t even the word. Continue reading

“Jen, Your Eyes Are Dark Like Shit So Maybe They Have Blood & Bile In Them”


No, that quote is not made up. Sadly, it was said to me while on a first (and clearly sole) date with someone.

I once went on a date with someone I met in a bar. I had only spoken to him for a couple minutes when he told me he had to run and asked for my number. We texted for the next week, and spoke on the phone for a little over an hour one night. Then he asked if I wanted to go to dinner that weekend.

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I Hate When My Male Friend Touches Me In A Bar & Other Guys Think We’re Together


There’s nothing worse than a guy not approaching me in a bar or club because he thinks I’m dating my guy friend. It’s one thing to have a guy not want to approach me, but to miss out because my stupid friend keeps touching my back or arm is just infuriating!

A couple weeks ago, I went out to a bar with two of my friends (one male, one female). For whatever reason my male friend, Mike, kept grabbing my arm while he spoke to me, putting his hand on my back, etc. Now, I know what you’re thinking — and you’re wrong. Mike was actually into my girl friend! He just talks that way!

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Make Me Put My Guard Back Up & You’ll Need A Guard


I recently wrote about a guy Ross (yeah, that asshole). The story from this post actually took place a day before he told me he could tolerate me.

Ross and I were texting after about a year of no contact, post-dating. At first he was sweet, you know, to lure me back in…then he went right back to being the ass I had blocked from my memory.

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“Jen, You’re On My ‘Shit-I-Can-Tolerate, But Wanna Smack A Little Bit’ List”


No, you did not misread the title of this post. A guy actuallyyyyyyy saiddddd thatttttt to meeeeeeee. Okay, deep breaths. In, out; in out.

Do you remember the post l’ll Go From Hot To Cold So Fast You Won’t Even Know What Hit You? Because he obviously did not.

Three weeks ago I began talking to a guy that I used to date. Now you know why I used to date him. Anyway, I was bored and sent him a cutesy text with 5 things I liked. (Greek salad, fuzzy socks, etc) and the fifth thing on the list was “When you entertain me.” I felt that it was less cheesy than saying “You” and sounded cute.

I got back a list of his 5 Likes, none of which had anything to do with me. When I jokingly inquired about this, I received THIS… Continue reading