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 »