From the time I was 18 until I was 25, I was almost always in a relationship. So when I moved to New York City in the Fall of ’04 to pursue my dreams, I welcomed being single with open arms. This was a time for me to be me and not Jess Connected to Someone Else. I was 3,000 miles away from everything and everyone I’d ever known and was chasing my dreams. This was my time to shine.

The first year was great. I delved myself into my studies, my social life in and out of school, and working. I was too busy for a boyfriend and I had countless experiences and made countless friends that I probably wouldn’t have if I’d been in a relationship at the time. I got to dive head first into the fashion and social world of NYC, something I’d only thought could happen on TV and had experiences where I often found myself asking, “Who am I and how the heck did I get here?”

As year two of being single came along, I was a little more antsy about finding someone, not to mention a tad embarrassed that I’d been in New York (a city of millions) for over a year and couldn’t find someone to snuggle with. But I was still livin’ the life and accepting my singledom.

Year three came and went - without a boy - and now that I’ve hit the four year mark, well it can be downright depressing.

I’ll admit it, having been single for four years has taught me a lot about myself and my personal independence: how much stronger I am (emotionally, mentally and physically) than I ever thought, and how I truly can make it on my own. In that same breath, though, it’s been extremely tough and oftentimes makes me question my self-worth: what could possibly be wrong with me that I can’t find a boyfriend? What am I doing that scares men off? I’ve gained a bit of weight, could that be the problem? Read More »

Some of us got lucky when we moved in. We had friendly, personable roommates who respected our space and kept us sane through finals week. Some of us ended up in one-room hell for a year. There are as many ways for a roommate to suck as there are humans on the planet, but here’s a few standout stinkers:

The Social Drinker
Or, in other words, the roommate that’s only social when she’s drunk. You spend the whole day together, share the same bathroom, use the same shelf for your snacks, and probably own the same deodorant, but the only things you say to each other all day will be “I’m going to class” and “Mind if I get the light?” You don’t hate each other or even dislike each other, but somehow you never seem to have a conversation longer than fifteen seconds. Unless it’s Thursday evening and she’s into the vodka, of course. Then she’s your best friend, and she always wonders why you guys never talk, why she’s never gotten to meet all your cool friends, how much she hated that stupid haircut you had at orientation, and eventually she passes out and you don’t speak to each other for another week.

The Invisible Woman
You know she exists, because you saw her parents on move-in day, and the pile of laundry in her hamper sometimes varies in size. But she’s never in the room when you come back from class, she’s never brushing her teeth or taking a shower, and nobody ever comes looking for her. There’s the empty shell of a human life: bed always made, textbooks neatly lined up on the bookshelf, television never turned on. Your room feels like it’s being haunted, as if there’s some presence only half there. Sometimes you see her outside, chain-smoking and looking waifish. Read More »

While you were up way past your bedtime watching Michael Phelps dominate the pool in Beijing, you probably missed out on some serious stuff happening back here in the states.

Like the fact that Hollywood is breaking apart at the seams.

Seriously, everyone is heading to break-up city! Even the rock solid couples…

Like Paris and Benji! Say it ain’t so! I thought this was the real thing. I thought this was forever. I guess “forever” in Paris’s mind means, “Until something more scandalous comes along that can get me back in the public eye.” This time, it was Chris DeWolfe, the Co-Founder of Myspace, that did the trick. And, while I liked the idea of her and Nicole having matching husbands, I think this new couple is a match made in heaven. She loves overwhelming the world with pictures of herself….and he runs the company that does just that.

I just can’t wait to see what kind of pictures/videos surface online from this relationship. A Night in Paris Part Deux? Read More »

God, it feels good to be single again. I recently broke up with my boyfriend of two years, and I know that this move solidified my future as an old maid. I know I’ll never find a guy more perfect for me than my ex, and that I’ll probably die alone. But, damn, it feels good to be single.

When you’re single, it can be hard to sit back and watch your attached girlfriends in their romantic endeavors. They get flowers from their boyfriends; they always have a date to a party; they have someone to cuddle with in the morning. But they also don’t have the opportunities that you have as an independent woman.

My (ex)boyfriend and I had been doing the long-distance thing for a while. I am currently trying to find my career path, but I had to keep trying to get a job close to him. This eliminated a plethora of job opportunities for me. When you get ready to graduate college, you can move anywhere you want or take any job that’s offered to you.

The girls who are involved have to make their life decisions with their partner. True, they can opt for the long-distance thing, but that still makes moving much harder than it does for you, the single gal with no emotional baggage.

Since reemerging onto the singles scene, I’ve also been feeling less stressed. Personally, I’ve had a lot on my plate lately, and I felt like even the daily “goodnight” phone call was cutting into what little time I have to spend on everything else. It takes effort to make a relationship work. True, it’s great to have a boyfriend to vent to or to seek reassurance from, but when you are trying to balance jobs, school, extracurriculars, and other responsibilities, sometimes it’s nice to be able to focus on you without feeling selfish. Read More »

You know those people that always seem to be in love? Annoying, right? But even more annoying, and frustrating, are those people that not only love freely but have their sentiments reciprocated. They bounce from one long-term, healthy relationship to another seamlessly, never regretting the past or even pausing for a good cry and a pint of Ben and Jerry’s.

And they make the rest of us look like emotionally immature, sexually frustrated, constantly single idiots.

But hey, you know what? Single’s not the worst thing. Because beneath the sun-touched, crystal-blue emotional coastline of those happy loving couples, there are gloomy storms. There are flashes of suspicious lightning and sudden tidal waves that crush the fishing canoes of stability on the rocks of impatience. There are the riptides of boredom that drown the surfers of passion. There is a dead seagull in the reeds, and it is gross and smelly.

Sexy and Stressed-out
One rather obvious downside of monogamy is that it isn’t polygamy. You can’t just go jumping every pile of bones in sight. And that might not a downside to some, since a sudden increase in sexual partners can turn your genitals into a giant bullseye for emotional instability, STDs and scary unwanted babies. But even if you aren’t planning on turning your dorm room into an all-hours Orgy 101 lab section, a monogamous relationship can turn even the most innocent girl-boy relationships into a nervous stressfest.

Maybe you’re visiting the guy you’ve been chums with since second grade, when you broke your hand launching your Big Wheel off of ramps you begged your dad to build. Maybe you’re going to catch a movie with an old friend who didn’t just bring his girlfriend — he brought the engagement ring to show off, too. Maybe he brought his boyfriend. The most physically intimate act you might commit is a badass fist-pound when you cut some guy off at a light. And yet, when you turn your cell phone back on, you’ve got four missed calls, a jittery text saying “were r youu!!!” and a voicemail that’s nothing but incoherent, angry sobs. And you’d say it’s paranoid and crazy, but at the same time, you know you’d be doing the same thing if he were having “a movie night with Katie” or whatever. People in relationships get protective, and it’s easy for that to damage long-standing — often longer-standing than the relationship — heterosexual friendships. Read More »

Put this under Things You Should Not Do If You Want To Remain A Happy Person: finding out what your ex is up to now.

To preface, I’m not talking about the person you dated for a month who you kind of cared about but never enough to commit and / or introduce him to your friends. If you want to look through that guy’s Facebook or Myspace, go ahead. Seeing him with his arms wrapped around another girl will probably do nothing but make you kind of glad you’re no longer seeing someone who thinks weird neck tattoos of skulls are cool.

But look, if you loved the dude (or chick), and it kind of ripped your heart out when things ended, do yourself a favor let them remain a mystery. Don’t try to find them on Facebook if you’re not already connected, unfriend them if you are, don’t ask mutual friends about who they’re dating, and for the love of god, DON’T GOOGLE THEM.

I am a naturally nosey person, but after The Big Ex and I split up years ago, I refused to seek out information on the girl he started dating a mere few weeks after our 4 year stint ended. I knew my friends had info, I could tell by their eyes whenever they tried to jump away from the subject, but I never pressed them. And when information was accidentally spilled to me, I made a conscious effort to change the subject and told people “I really don’t care to know”. It was hard, because I did care to know, but I knew that need for knowledge was coming from a macabre place in my brain that loved to torture the rest of me. Read More »

My first night back in Los Angeles, after a year of living in New York, I ended up at a bar on Sunset called Coach & Horses. It was dark, dank, a jukebox kind of place. I started talking to a guy, a friend of a friend, about our jobs, favorite movies, favorite television shows. He worked in the writer’s room of a popular TV show, we were both addicted to “Top Chef,” and we agreed that the first four seasons of the “West Wing” were brilliant and far surpassed seasons five thru seven.

It was refreshing to talk to a guy who shared my interests and taste, because in New York it was hard to find someone I had anything in common with. I felt like I’d struck gold, and then I remembered: I wasn’t in New York anymore. This was Los Angeles, a city full of my kind of people.

It’s not just a myth that everyone in Los Angeles works in the entertainment industry in one capacity or another; you’re hard pressed to find someone with no industry connections. Everyone in LA seems to have a script they wrote tucked under their arm, and most would rather win an Oscar than a Nobel Peace Prize. Some might hate this, but I love it and talking to this guy at Coach & Horses felt incredibly good. Read More »

As that song your mother listens to on the Oldies station says, “breaking up is hard to do (oo).” Especially these days when people have all sorts of options when it comes to communication. It sometimes seems that people sit down and contemplate the absolute worst way to dump someone…and then do it.

Below is my list of the top five ways to dump someone. If any of these have happened to you, I feel for you sister; I really do.

1. Instant Message. A friend of mine was recently dumped via AIM. By her boyfriend of six months. Six freaking months and he didn’t have the decency to do this in person. The last time I was broken up with on instant messenger was in 8th grade, and even then it was barely acceptable. Any self respecting male over the age of 15 should muster up enough cojones to do their dirty work in person. Douchebags.

2. Text (Rusty Cartwright style). This method is highly unrealistic, at least in my experience. For me there would be no confirmation; the jerk would just disappear off the face of the earth until I ran into him at 1 am in sweatpants at the library. Still, the guy who employs this tactic is a little bitch, in my own humble opinion. If you are ever or ever have been dumped in this manner (or the aforementioned AIM breakup) then you probably don’t need me to tell you that honey, you are waaaay better off without that prick. Read More »

Last Sunday night I found myself at Barney’s Beanery in West Hollywood. It was Memorial Day weekend, so the bar was packed. I’d come with friends, so I wasn’t looking to talk to any guys, but looking around I was surprised at how many cute, normal looking ones there were.

There were tons of adorable nerdy boys wearing glasses and semi-skinny jeans who looked like they’d just come to chill and have a good time with their friends. Yeah, there were a few desperate-looking ones in buttoned-down collared shirts and pressed slacks, but I just ignored them. I couldn’t understand why my friend S (identity protection) always complained to me about not being able to find datable girls in Los Angeles, there seemed to be plenty of cute guys. So I decided to put myself in his shoes, and I looked around for girls. It was an eye opener.

To start with, there were five guys to every girl, and for every normal-looking, attractive girl, there were ten über-slutty ones. I saw one majorly stacked blonde wearing a blue dress so low cut I could practically see the surgery scars on her nipples. Fake tans, platinum extensions, and cheap stilettos were everywhere. We weren’t in some swanky bar on Sunset, and these girls weren’t going to find their future investment banker husband here, this was Barney’s, a bar full of currently unemployed, future TV showrunners. I suddenly felt incredibly bad for S. Read More »

Today, while sitting in the salon in my hometown and having the prerequisite hairdresser chit chat with the guy who’s been doing my hair since high school, the old “so, you got a boyfriend?” question came up.

These days, I don’t even try to stop my chuckle when I answer, “nope”.

We talked a little about why my river has run so dry for so long, and as he ran his scissors through my bangs, my hometown hairdresser goes “well, it’s probably because you’re a real person.”

This is not the first time I’ve been called real. And it’s not the first time this “realness” has been connected to me being single.

What are we to surmise from this?

Does being real immediately put me in some kind of realness cage? A desolate place where people who can’t be anything other than themselves are gawked at by the rest of the fake society? Is being real like having some kind of horrible birthmark on my face — something that frightens potential suitors away with its blatant obviousness? Are we real people like the cyclops kitten; so weird no one wants to get too close but can’t exactly look away? Read More »