OyChicago blog

I consider myself a late bloomer. My first kiss took place my senior year in high school while I was on winter break with my family and I didn’t have a boyfriend until senior year in college. No one asked me to prom and I’ve only said, “I love you” to one boy.

I’ve had my share of casual dating relationships and one dating spree— it ended quickly when I started mixing up my dates’ names. I’m definitely not the most experienced relationship girl, but thanks to some good luck and determination on his part, I have been with my boyfriend Jason for five years.

We met in the fall of 2006. I’d already been in two relationships that summer and was actively trying to be single for awhile. When I graduated from college, I also graduated from my first real relationship. (I know it sounds cliché, but it was true.) He was a few years older than me and a “townie” with not much of a future and I was returning to Chicago. I knew we had no forever-after together and it didn’t take me long to rebound. A week after graduation, I went on my birthright Israel trip, where I fell fast and hard for a fellow participant. In retrospect it was silly, but Israel brought out the naïve romantic in me and I’d pretty much convinced myself by the time I got back to Chicago that I was going to marry this guy. It didn’t help that everyone else on my trip thought so, too.

Well, we got home to Chicago and tried to date for a bit, but it fizzled quickly and dramatically (at least on my end) and as a way to distract myself from the pain, I rebounded again with a guy and an awful pick up line, “do you have a piece of gum?” He turned out to be perfectly nice with a perfectly nice summer internship in Chicago that guaranteed the fling would last only as long as the warm weather.

In late August, I moved into my own apartment and set out to be single girl in the city. I’d clearly been getting into relationships too quickly with the wrong guys (even the perfectly nice one) and needed a break from the dating scene altogether— my own dating detox. But one random Friday night soon after, my cousin asked me to attend a party in the suburbs being thrown by his sister’s boyfriend’s younger sister. Did you follow that? Well, I barely did and I didn’t want to go spend a night with a bunch of random people I didn’t know in Glenview. As part of my dating detox, I was actually enjoying spending Friday nights cooking dinner at my new place for my girlfriends. But at the last minute something made me change my mind and I decided to go.

He was the first person I met that night. It was raining and he’d been outside trying to grill food for the party. He had this big, adorable grin on his face and was soaking wet, which just made him even more attractive. You could tell from his happy, outgoing demeanor that he was the kind of person everyone wanted to be around all the time, including me…but just as friends. Later that night, I learned he was single, which meant that it was my job to set him up, but not with me, with one of my friends. Yep, little-miss-matchmaker was so preoccupied matchmaking for others (and trying to be single herself) that she attempted to set up her beshert with someone else.

Fortunately for me, my set up failed— neither my friend nor Jason had any interest in the other person— and after several weeks of wooing on his part, I gave in. Best decision I ever made. Being single is overrated when the right person comes along. And sometimes your gut just knows its right even when the rest of you hasn’t caught up yet. Bottom-line, you can do everything wrong and still end up with the right person—even when you least expect it.