Welcome to Ask A MWLTF (Yes, that’s Mother Who Likes to F*ck.), a monthly anonymous advice column from Scary Mommy. Here we’ll dissect all your burning questions about motherhood, sex, romance, intimacy, and friendship with the help of our columnist, Penelope, a writer and mental health practitioner in training. She’ll dish out her most sound advice for parents on the delicate dance of raising kids without sacrificing other important relationships. Email her at askpenelope@scarymommy.com.

Dear MWLF,

I’m the mom of two great kids, and two years ago, their father and I had an amicable divorce. After taking some time to enjoy my new single life and reconnect with myself, I decided I was ready to get back out there and download a bunch of dating apps. This was all new for me. My ex and I had married at a time when if you wanted to go on a date with someone, you had to go up and talk to them first. I was intrigued and excited when I realized this awkward hurdle had been removed by technology. I made a cute profile and went at it.

About four months later, after going on, I don’t know, two dozen dates with random suitors, I was ready to get myself to a nunnery. I like to think of myself as a pretty open-minded person. I’m not especially shallow, I don’t really care how much money someone makes or how tall they are or if they can run a marathon. And having just gotten out of a long marriage, I also wasn’t looking for a super-serious commitment off the bat. And yet still…wow.

In my four months of internet dating, I met men who seemed perfectly nice by text, then turned out to be in the throes of active alcoholism, housing insecurity, or extreme financial crisis. I met a man whose divorce had caused him so much stress he’d ground out all his teeth. I met a man who was beginning to rebuild his life having recently left a cult. I met angry men and impotent men, cheating men and narcissistic men. After four months of dates that ended up feeling more like therapy sessions with me as the therapist, I’d pretty much decided to close up shop and live out the second half of my life with my other divorced friends and a series of canine companions. There were worse fates.

Then, just when I’d given up, I ran into my son’s eighth grade teacher at a coffee shop. We started chatting, first about school, then about a bunch of things that had nothing to do with school. I felt a real connection, but figured nothing would come of it. Then I ran into him at the same place the next weekend, and once again ended up talking for hours. What can I say? I’m smitten, and I sense the feeling is mutual.

However, when I mentioned the connection to a friend, she seemed concerned. Wasn’t I worried about crossing boundaries? What if…. and then she laid out a variety of scenarios that might lead to the teacher getting fired or my son finding himself caught in the middle of my love life. I can see her point. I’d been so thrilled to have felt an authentic connection with a seemingly decent human that it didn’t occur to me I might be treading down a dangerous path. I don’t want to make a mess for anyone, especially my kid. At the same time, I really like this guy. Obviously dating my son’s teacher is less than ideal, but is it absolutely off the table, or is there an ethical work-around?

Dear Less-than-Ideal,

As a late Gen-X’er who paired off right before the age of swiping, then found myself navigating its gory workings in middle age, I often ponder how odd it must have been to be a single adult dating before the internet. When I ask older friends and family how they met people back then, their answer is generally something like, “You went places and talked to people, and if you liked them, you asked if you could see them again.” It was almost like the entire world was one giant dating app, except instead of liking and swiping in solitude, people engaged in real-time human interactions. It must have been exciting. It also, I imagine, must have made the boundaries between who and where one could date more porous.

Today, with many workplaces discouraging romantic entanglements (for some good reasons), it almost feels transgressive to find oneself romantically drawn to a person who isn’t a stranger, especially when that person plays a role in some other aspect of your or your family’s life. When I brought your question to one friend who worked for decades as a high school history teacher, his response was unequivocal. “Don’t do it,” he said. “The quality of your child’s relationship with their teacher is one of the most important predictors of their emotional and academic success. If you start dating one of those teachers, there’s no way not to create a triangle. Your kid’s relationship with the teacher could now be compromised by your own.”

It’s hard to argue with this logic. Boundaries are essential in maintaining healthy relationships, particularly in a school or work setting, and especially when children are involved. That said, I found myself, like you, wondering if there wasn’t some way to take a softer stance. When I asked another friend who worked in education administration for several decades, she could see the dilemma. “As every single parent like me knows well, time is precious, and it’s really, really hard to meet someone worth your time. If there’s a real connection there, it’s just too rare to squander.” For her, the answer seemed to be dating mindfully. “If you’re just dating to have fun, then your kid’s teacher is not the right person for that. There are a lot of people you can have fun with. But if you're dating with intention and looking for a serious relationship, then you should really be going about it very slowly, getting to know someone for a long time before you introduce them to your kids or family.”

She went on to note how these days the term “dating” has become synonymous with being in a relationship. “But dating can actually mean going on dates with someone. Getting to know them. Having coffee with them. It’s okay for that stage of dating to last a long time. If you have kids, maybe it should. And last I checked, the school year is only nine months.”

The bottom line is that while boundaries are important, there’s also real value in meeting people you encounter in real life, not only through apps. And when you have kids, much of your life revolves around them and the other adults who play a role in it. That being the case, pacing, patience, and mindfulness might offer a third path between squelching a budding connection and throwing caution to the wind.

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