Why I Bring All My Baggage on My First Dates

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Welcome to It’s Complicated, stories on the sometimes frustrating, sometimes confusing, always engrossing subject of modern relationships. (Want to share yours? Email pitches to itscomplicated@nymag.com.)

When I first reentered the dating pool after leaving my husband, I made a surprising discovery: Apparently, sometime during the decade-plus that I’d been married, all the single men completely forgot how to read.

At the time, I was feeling, well, like someone who hadn’t been on a first date in more than ten years. I was scared, I lacked confidence, and even though everyone I knew was telling me to “put myself out there,” I had no idea how to do that. So one night after my kids were in bed, I enlisted the help of a friend and some liquid courage, and I made myself a blatantly honest, completely straightforward online dating profile — no spin, no filters. I’m a single mom with a demanding job and not a lot of spare time to waste; I figured the more I shared about who I was, the better.

After a few super-awkward first dates, though, I learned how optimistic it had been to expect the men who contacted me to pay attention to what I’d written. Each and every time, I found myself struggling to keep my anxiety in check as I stumbled through an explanation for something I assumed my date already knew. Things listed front and center in my online profile were treated as total revelations, and usually not for the better:

You’re a vegetarian? How can you be a vegetarian? What about bacon?! This guy seemed actually angry, for some reason. But it was literally in the second sentence of my profile, and besides, how could I have known that bacon-hate was a red flag?

You’re divorced? I don’t believe in divorce. Marriage is forever. Check, please.

Why didn’t you tell me you had kids? I can’t date someone with kids. Um, see my profile, first sentence. Besides, my kids are awesome. Your loss.

For those first dates that made it past the initial round of drinks, I faced another challenge: how to disclose the things that I hadn’t already shared online. I’d been out of the game a while, sure, but I was pretty sure that divorce, trauma, mental illness, and existential crises still weren’t really first-date material.

On the other hand, hold on to a piece of information long enough and it starts to look uncomfortably like a secret, and I wasn’t ashamed of the tougher parts of my past. I was just in uncharted territory. How soon do you share? How much is too much? I had no idea.

* * *

Eventually, enough bad dates made the decision for me. The more dead-end evenings I spent with someone who clearly wasn’t a good match, the sillier it seemed to hold back. So I decided to conduct my own little dating experiment: I would lay everything out on the table from the beginning, with everyone.

The results were … let’s call them mixed. I quickly learned that radical transparency was more complicated than I had planned for. Mentioning my divorce was one thing, for example, but when was the right time to explain that my ex-husband was an abusive serial cheater? I wanted to share this — it’s an important part of my story, one that any potential partners should be aware of — but when one date asked me why I left my ex, I told the truth, and instantly regretted it. In a misguided attempt to commiserate, this guy told me that he had left his ex-wife because he “felt like [he] was going to hurt her.” Yikes. I’m still not sure if he thought he deserved a cookie for not abusing her, or if he was just trying to make conversation. I didn’t stick around long enough to find out.

Another time, we got into the heavy stuff before we even met in person. We’d been chatting for weeks; the night of our date, I put on my favorite black-and-white checked dress and cherry-red lipstick, and arrived early at the bar. As I sat sipping my glass of wine, he texted me: “Sorry, you have too much baggage. I changed my mind.” I was so hurt, I didn’t reply.

Then there was the first date that seemed perfect. We had such a great time that I invited him back to my apartment to watch a movie. I told him about my ex, and he was so gentle with me about it, telling me that it was not my fault. But then we started kissing, and his sexual aggression made me freeze and then panic. How do you tell a first date that you’re a survivor of sexual assault? I couldn’t get the words out, so instead I got up and asked him to leave, shaking. Some baggage, it turned out, I wasn’t quite ready to volunteer.

Still, I wasn’t ready to give up on my commitment to presenting the real me up front. So I amended my strategy: I wouldn’t bring up the heavy stuff on my own, but I’d answer all questions honestly as they came up. It was a happy medium between hiding and awkwardly oversharing.

The next first date I went on was with a person I’d been chatting with off and on for about a month. It helped that by the time we met in person, we’d already discussed some of the important details online: He knew that I was divorced, and that I was a single mom. During our date, when he asked me why I left my ex, I told him. He said, “I am so sorry that happened.” Over a few cups of coffee, I learned some things about him, too — like why his marriage had failed, and his struggles with single parenthood, so similar to mine. He told me about his history of mental illness, and I told him about mine. Then he asked if he could hold my hand.

Experiments need to be replicated to be considered valid, so you might wonder what happened the next time I went on a first date. Fortunately for me, though, I don’t have any other data points to share — that man and I are still together, and married now. Schlepping all my baggage to my first dates, it turned out, was exactly what this divorced single mom–slash–sexual-assault survivor with anxiety and an abusive ex needed in order to find someone willing to help me carry it. And what seemed like weight, in hindsight, now feels more like a solid foundation.

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