After a pretty excruciating breakup last year, I took some time off from dating. I’d been in and out of relationships since my separation three years earlier, and I was definitely due for some “me time.” My dating hiatus was lonely but necessary (and mostly well-spent). When I finally felt ready, I made plans and sat waiting for my date at the bar of a restaurant, sipping one of the best martinis I’d ever tasted. It had been an exhausting day, but I forced myself to go on the date anyway. I was trying to stay open to new possibilities. So I scrunched my curls and dabbed my cheeks with one of those newfangled lip-cheek-everything stains, and arrived with hope in my heart. Within moments of his (very late) arrival, I knew I wasn’t interested. It had little to do with the fact that he looked nothing like his pictures, but more that there was no chemistry between us. I carried the conversation, and I couldn’t help but notice that he was hungover, and even shaking, from energy drinks, which he casually revealed was the cause. He couldn’t even eat his beef bolognese (which I’d told him was the best thing on the menu).After chatting for an hour, I asked for the check and, as kindly as I could, let him know that I didn’t feel a strong connection. I could tell he was disappointed while we both awkwardly picked at our food, but so was I. I’d psyched myself up to go and meet someone I’d been having witty banter with via text for weeks, only to be utterly let down.As I drove home, I remembered all too well that opening your heart also has high potential for disappointment. I tried to push away the sinking feeling that maybe I’d been lucky in love too many times. What if I never met someone I had something genuine with again?
Though entering the dating pool (again) felt like a big deal, I knew I’d likely have to sit with my feelings alone. When you’re young and bummed out by a bad date, you get on the phone with a friend. The venting feels good, and it helps you shake off the feelings of dread or dejectedness that may be tugging at you.I fondly remember lounging around friends’ bedroom floors in high school and college, spending hours dissecting practically every interaction we had with guys. Of course, that kind of time-consuming—and probably excessive—bonding is not something for which most people in their 30s have time. (I know I don’t.) But these days, I tend to handle even the most brutal dating and relationship struggles on my own. I’ve barely spoken about every breakup I’ve gone through since my separation, except with a therapist. And last year, when a man I loved moved out of my house, a man whom I thought would be the stepfather to my children, it was essentially the same. A few days after the last of his things were cleared from my house, I met my best friend—who is happily married—for dinner. I was shaken, and though she knew he had only just left, she didn’t ask how I was coping or offer any words of kindness or encouragement. When I mentioned him, she brushed me off, as if it wasn’t at all important.What she didn’t know was that the experience had rocked me even harder than my divorce because I genuinely wanted to maintain a relationship with this man. It was almost like there was the expectation that because I’m a grown adult—not a teenage girl, or a college student—I should be able to handle whatever comes my way. After a previous breakup, she had told me, “Well, you’re the one who wanted to date.” It made me feel like I was no longer worthy of support. I had chosen divorce, after all. If I struggled, it was my own fault. I couldn’t shake the feeling that she thought my post-divorce dating struggles were juvenile. I told myself it’s easy to forget how hard dating is when it’s been over a decade since you’ve been single. Yet I still felt like I was being unfairly judged because I hadn’t immediately fallen into a perfect dating scenario or managed to make something last.
Perhaps it’s common to judge women who are dating post-marriage, but feeling like you can’t find a friend with open ears is isolating. And being a single mom is already a pretty isolating experience on its own. It should go without saying that divorced and dating moms need outlets, too. In the same way that our newlywed friends want to talk about their marriages, we should be allowed to talk, vent, and share about our dating lives. We don't deserve to feel like we are burdens for wanting or needing that. Far too often, though, that’s exactly what happens. Breakups can be devastating at any stage of life, but personally, I’ve struggled more to feel resilient as a divorced mom who hasn’t decided to give up on dating. It’s not that connections are harder to come by now—there are amazing people everywhere. Rather, it’s harder to make relationships work after you have kids, an ex-husband, and an idea about the shape of your life. No one is as pliable as they once were. On top of that, life in general is harder, and therefore, so is healing. Having compassionate friends who want the best for you—whether you’re married or single—is still undeniably important. Unfortunately, that is what feels hard to come by.
The next day, as I shook off the bad date, threw on clothes, and got ready for work, I got a text from a coworker—a divorced mom who had become a close friend in recent months. “Hey! How was your date?” she wrote. I smiled to myself and felt instantly filled with the exact kind of simple and genuine support I was craving. I realized in that moment that just having someone ask was all it took to feel a little lighter. I don’t need a huge circle of friends at this stage of my life. Quality, to me, is much more indispensable than quantity. It's why I've come to value the few authentic connections with other divorced mothers so deeply, and people who are willing to go outside their own experiences and not judge what they don’t understand. Truly, this stage of life is genuinely hard, but there is so much beauty and self-discovery in it, too. I wouldn’t trade it for anything. Having the support of a few good friends helps me to get through my rough moments and to keep feeling empowered through it all. Craving true connection? If you’re ready to date like a human again, sign up for early access to the forthcoming Keepler dating app here.
