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 »

When I told my friends that I went and grabbed a drink by myself at Happy Hour they were shocked. “Don’t you know how that looks?” they asked me. Many women think it looks like a move you pull when you’re trying to get laid, when really, maybe all I was trying to do was get a half-priced glass of Sangria and Buffalo Wings (don’t judge the pairing, it’s delicious.)

Independence is attractive. Having enough confidence to say “table for one” is beautiful, and frankly, quite difficult to acquire. TwentySomethings are generally surrounded by people, all. the. time. From roommates to classes, parties to multiple job hopping, mixers to double dates, in between it’s hard to find that sacred time of solitude. It’s often easier to stay surrounded than to forge out on your own, because being alone means there are decisions to make; what you want, sans your friends influencing opinions (God love them).

Do you order Chinese food every night because you’re craving the same Chow Mein you’ve been eating for the past week or because your roommate always gets it? Do you really want to see 27 Dresses AGAIN, or is there an Indie flick you’ve been dying to catch….? The truth is until you do things for yourself it’s terribly difficult to answer these questions because you’ve never asked yourself what YOU wanted before.

This is no simple process. Alone time scares many a confident person. Knowing where to find your fulfillment outside of friends is often hard to do. Friends fulfill me, sharing fulfills me, my family and the random dude who engaged in conversation over a beer pong table (sometimes) fulfills me. But, on some days being able to sit with a cup of tea, or take a walk with my Ipod fulfills me more than ANY OF those things.

Here are some suggestions for those of you who are looking to move forward into your lonesome with grace, excitement, and security. Trust me, after a while, you’ll learn to LOVE IT: Read More »