Illustration: Alice Zhang
I received my first dick pic on public transit, after dropping my kids off at school. I wasn’t even halfway through my latte. New to dating apps and dating in general, I’d been chatting with another recently separated soul. We were planning to meet for what would be my first date in 20 years when a pixelated icon appeared. As a safety precaution, I had to tap to actually open the picture, which should tell you a bit about what can happen in dating apps. I closed one eye and reluctantly opened the image, hoping it was a puppy.
The photo that greeted me was later dubbed “the worst dick pic I have ever seen” by a millennial colleague, a self-proclaimed expert who had allegedly seen hundreds of them. I was livid. Yes, I’d been flirty, but I had not requested this. I replied with all-caps anger, then blocked him.
Unwanted dick pics aside, the bigger truth I had to face was how I wanted to participate in sexting culture. When I downloaded several dating apps shortly after my 17-year marriage ended, I was venturing into a brand new world I knew little about. I knew even less about how I would like to be treated in this world.
Does everybody sext now? In my experience, if you’re actively dating the answer is yes. As I’ve learned firsthand and also through my work as a coach supporting women through new life experiences, online dating and sexting are not all bad. A lighthearted approach to the latter can help you explore and understand who you are as a sexual being and allow you to connect with your desires. All it takes is the right attitude, some common sense and a willingness to push yourself, ever so slightly, out of your comfort zone.
Prior to my divorce, I had not dated since the early days of the web. Unsurprisingly, perhaps, I was immediately shocked by the behaviour of the people I came across on apps. Men asked where I lived, what colour bra I was wearing and what my sexual appetite was—within moments of chatting. I felt unsafe and uncomfortable, but I convinced myself that I had no choice but to accept sexting as the price of admission for my search to find love and sex again.
Soon, I was having eight to 10 very flirty conversations all at the same time, via direct messages with different men in different dating apps. (I started out on Tinder before trying Bumble, Plenty of Fish, OkCupid and finally Hinge.) After two decades of sleeping with the same person, I felt overwhelmed. I also realized that I had some social conditioning to undo. Growing up in a traditional Armenian household and being taught about Christianity through Catholic school, I internalized stories that made me believe women should not own their sexuality and that wanting sex was shameful. Fast-forward to now, and sexting was everywhere. I was forced to confront my own apprehensions. Sure, I could choose to not use dating apps, but the bigger issue was that I did not know how to connect to my own desire. And so I decided to lean into sexting. Here’s what I’ve learned.
Feeling unattractive after my separation, I knew I needed to feel better about myself in order to be flirty with other people. So I stood naked in front of the mirror every morning and tried to identify a body part I liked. I ordered lacy underwear sets. I began to post selfies on days I thought my outfit was cute or my hair looked good. The instant validation from friends, colleagues and admirers encouraged me to play with my new identity as a single woman, to claim space and to really start to see myself as beautiful again.
Another piece of advice: Practise texting sexy sentences to yourself through the Notes app on your phone. What would you ask for if you weren’t embarrassed, scared or feeling shy? Learning how to speak your desires is an essential practice for women who have traditionally suppressed their wants to be more agreeable to partners and authority figures.
My first foray into advanced sexting began after a lunch date with a sexy-accented European intellectual, whom I quickly dubbed El Profesor. We shared a kiss under umbrellas, and I was elated when he texted later that day to say he’d had a lovely time. Then he sent a selfie of himself looking dashing in a blazer. My curiosity was piqued. When he asked for a selfie in return, I quickly posed in my T-shirt, snapped and sent. A second selfie appeared, this time with his blazer removed, followed by the caption “Your turn.” Huh?
Panicked, I shut down the conversation. Later, I decided El Profesor could be my gateway to getting comfortable sexting. The next night, feeling a bit tipsy, I put on my best negligee, crawled into bed, took a deep breath and snapped some photos. Careful not to include my face, I sent a pic of my cleavage. Game on! Things progressed in surprising ways, with photos volleying back and forth. Did I enjoy it? To be honest, it wasn’t my favourite, but I felt like I’d ticked another sexual milestone off my rookie list. What I couldn’t shake was the feeling of shame. I’m a mom! What if my kids found these images? I quickly deleted the pictures and the exchange.
After our first sexting session, El Profesor’s “Wanna play?” requests came in night after night. I did not have enough outfits to play this game. More importantly, I realized I was performing. “I’m sorry, but I don’t think we’re a romantic fit,” I texted, feeling proud for being true to myself.
Following a summer of first dates and sexy flings, I took a seriously long break. On my next round, sex was still a driving force in many conversations, but I had changed my approach. The photos I shared were fun but not salacious, and I was clear about what I was looking for: “You’re for me if you’re also looking for a Jane Austen–style slow burn in lockdown.” This helped eliminate those looking for instant gratification. I also began to pay attention to which conversations made me feel good, and which ones brushed up against what I now knew were my limits.
Getting comfortable with rejection, both giving and receiving it, is crucial when online dating. So often as women, we feel we have to be nice and placate the other person. But in online dating, the other person lives in your phone. A polite “No, thank you, that’s not for me” is a good way of telling someone their message didn’t land. If a bruised ego leads to persistence or insults, simply block and delete.
After six months of being single between spurts of dating, I met a man who helped me release my shame around desire and pleasure. After we’d casually dated for a few months, he texted one night to ask what I’d like to do on our next date, I responded with a cool “What were *you* thinking?” He sent back a parade of words so salty, I would be mortified if my mother ever saw the interaction. More racy messages followed. Receiving these texts thrilled me every time, but I still felt intimidated when trying to reciprocate. I wanted to write super-spicy comebacks, but it just wasn’t in my wheelhouse.
Despite the great sex and conversation, that relationship fizzled out. I fired up the apps yet again and soon fell in love with a man who was “just right.” Our sexting was playful; I would often burst out laughing and simultaneously be turned on. Returning his banter exercised a part of my brain that I had closed off for decades. Turns out, I’m pretty good at sexting with the right person—it was just a matter of figuring out what that looked like.
I have no regrets about my trial-and-error phase in the wide world of sexting; it made for lots of learning and some really great stories. I’ve discovered I’m not a Playboy photographer, nor a bunny, and that for me, my flirtations are best left for face-to-face conversations. I’m currently single again, but the next time I receive a sext, I’ll know how to respond in a way that feels true to me.
The internet is forever. While you might trust the person you’re sharing with, it’s far too easy for the recipient to screenshot and share. This goes for texts as well as photos.
Apps like Instagram and Snapchat have a disappearing-photo messaging option. (But be aware that the receiver can still take a screenshot of the image.)
Keep explicit photos “hidden” through your phone’s existing photo app, or use a password-protected photo album or app. This is especially important if your children have access to your phone.
Over time, you’ll get good at trusting your gut. Until then, consider paying for a fake number (also known as a burner) that you access through an app on your existing phone. Texts and conversations will remain within the app, which you can bury in a folder that your kids won’t look in.