OyChicago blog

Once upon a time, I was lucky in love.

Nathan and I hit it off at his 20th birthday party at Washington University in St. Louis. We became fast friends between the kisses, parties and laughs.

Several months after we started dating, I joined his intermural Ultimate Frisbee team and sprained my ankle colliding with a teammate. After the game, Nathan helped me up the stairs to my apartment and fetched me an ice pack. It was the first time someone wanted to take care of me -- and make out with me. Isn't that all anyone ever wants?

Throughout the next several years, Nathan helped me understand sports and politics. He was brilliant, humble and hilarious. He could kick most people's butts in racquetball. He loved to travel and explore restaurants with me. Somehow I had found an amazing man -- I always told him how lucky we were.

It wasn't all peaches and sparkles all the time, though. After our first year of dating, we did the long distance thing when I took a job in Indiana and he had a year left of school. When it was over, I didn't hesitate to join him in Milwaukee as he began medical school. Three years later, my job ran out of funding, but I got an offer in Chicago -- the city where Nathan was hoping to match for his residency; the city where we were both born and had family. Doing long distance again after more than four years together was not ideal, but we knew it would be temporary.

Then came Match Day, and Nathan matched in Milwaukee. He was upset. He was looking forward to a change of scenery, and he wouldn't get it for another few years at least. I cried about it, but knew it would be harder for both of us if we weren't together. Things were better for both of us when the other person was around.

A month later, Nathan proposed at the Trevi Fountain in Rome, the pinnacle to a wonderful, nearly two-week adventure. "Ilana, I love you. I want to do it all with you. Will you marry me?" It was the happiest day of my life until the day we got married.

I came back from our trip and started looking for jobs in Milwaukee again (while wedding planning), hoping to find something before my lease in Chicago ended. When I came up empty, I moved in with his parents in the suburbs to at least shorten the distance between Milwaukee and Chicago. By December, I quit my job and moved back to Milwaukee without anything lined up. Again. For him -- for us. We were married in May.

^{Ilana and Nathan on their wedding day.}

It was just a year ago January that I remember sharing with Nathan some amusing anecdote about a colleague's dating misadventures. We both chuckled, glad that we didn't have to date as adults. I told him it sounded hard, exhausting and frustrating. How lucky we were, nearly nine years after our first kiss, to only have to date each other.

And then, one month later, Nathan died unexpectedly. Needless to say, I didn't feel so lucky anymore. I was a widow at 29 years old.

The day after I finished sitting shiva for Nathan, I told my boss that I wanted to move back to Chicago. I felt a strong need to continue cultivating my relationship with my in-laws, and brothers-in-law. I spent the last nine Thanksgivings with them, including this past one, the first without Nathan. They were my family. I wanted access to a vibrant city, where I could run into old classmates at events or on the street. I needed to be in a city where people knew me before I was a part of "IlaNathan."

Of course, I also knew I needed to be in a city where there were other Jewish unmarried 20- and 30-somethings, people with whom I could learn, laugh, explore and hopefully -- one day -- love. In Milwaukee, my friends were almost entirely couples getting ready to start families; the Jewish life there was stifling and devoid of ample age-appropriate single, Jewish men.

For months and months after Nathan died, my heart wasn't open to letting another man in, yet my fingers were going through withdrawal without Nathan on the receiving end of my texts. Maybe I wasn't ready for love, but I needed something -- someone -- to fill this tremendous void, someone to check in on me, flirt with me, admire me, and, yes -- send me thoughtful emojis.

I asked other young widows what was appropriate. It turns out, there's no Emily Post to guide you through the dos and don'ts of widowhood. They said anything that made the days more manageable -- that made me feel less sad in the moment -- was the right thing to do. "You do you," is a common mantra among this peer group.

Regardless, friends were surprised when I went on my first first date in nearly a decade. Friends judged. Friends were in disbelief that I was moving forward, and that I was no longer part of the couple they had admired for so long.

^{Ilana (bottom right) with Nathan's brothers and their significant others.}

I judged too. I too was in disbelief. On my second date, I left and cried the entire car ride home. Is this my new life? Going out with guys who live in apartments that smell like a locker room? Guys with makeshift coffee tables made out of plastic hampers, littered with papers and unidentifiable sticky substances everywhere? Guys who need convincing that an eight-hour first date is a bad idea? Having to explain to these guys what happened to the one I was with for nine years?

Apparently, this is my new life.

At first, I was upfront about being a widow. I included a line about it on my dating profiles. I didn't want to waste my time with someone who wasn't emotionally mature enough to handle my loss. But as time went on, I decided that wasn't fair. Most people don't include their dating history on their profile -- why should I?

Eventually, the "W" I felt emblazoned on my chest faded. My coping mechanism of choice has been to schedule myself stupid. I am determined to continue putting myself out there, to meet people who can introduce me to more people, to cast as wide of a net as possible.

So far, I have met people at happy hours, alumni events, Shabbat gatherings, speed-dating events, and a ton of other young professional programs. I smiled. I drank. And I told my story.

I joined a book club and told them about Nathan. I opened up to my colleagues about why I quit my last job and moved to Chicago. I'm sure I have made a lot of people uncomfortable -- but I'm not sure I care.

^{Ilana (right) at a Jewish young adult event.}

And I've continued to date, mostly through the online dating platforms I never thought I'd have to use. And it is exhausting, frustrating and hard. I've been on maybe two or three dozen dates since Nathan died. I've cried after some, and harder after others.

But I'm opting to spend much of my time offline, because it only takes a few minutes of talking to someone to know if there's potential for romance, or to find out that they're younger than 26. Of course there isn't anything inherently wrong with being in your early or mid-20s, but I know in my heart of hearts that as a now 30-year-old widow who at one very recent point in time had baby names picked out with her husband, men of a certain (younger) age simply aren't going to get me.

The loneliness can be consuming, but I know I'm not alone in my quest to find another Jewish partner. I know I'm not even alone in knowing what I'm looking for, though I don't know that I'll be able to recognize it in a package that's not Nathan. I know there are others my age (and older) craving events that offer a better chance of developing more meaningful connections.

So I continue to look for my next beshert, sometimes with a slightly jaded outlook after now being alone for a year -- sometimes with a more hopeful outlook when I meet someone inspiring, someone who makes me laugh and is able to teach me about something I wouldn't have otherwise known.

There's still so much I don't know, but one thing I do know is that as sad as I am and as unlucky as I feel, I'm lucky to have known Nathan. I only hope that one day, someone else feels as lucky to know me.

For more stories in the "Single, Jewish and Figuring It Out" series, visit oychicago.com/single.