I had been looking for my Option B, so it was time to use one of those dating apps. I tried to network, but all of my friends’ friends — to quote one potential connector — were “either married, divorced with like 10 kids, 50 or older, gay, and/or totally horrible.”

I’m 36. I am an innovative, hardworking educator. I have had successful previous relationships. I’m smart. I’m funny. I’m successful. I’m super-pleasant, most of the time. Sure, I was widowed at 27, but we all have our baggage.

I’ve had fits and starts. I was engaged to a lovely guy, but then he died. (Pour one out for that lost love. Thank goodness I’m well-adjusted now.) There was the time, after that, when I got engaged to another guy, but he lost his mind and humiliated me. I’m grateful now that he dumped me spectacularly. There was the Sephardic guy, who seemed like a good idea until he kept on dismissing everything I had to say about Judaism, even though I’ve been teaching about it for the past 20 years. There was the Israeli guy who had a wife and had been “meaning to get divorced” but hadn’t gotten around to it.

Boys, bye.

Here we are. Again, after so many fits, we find our reluctant heroine at one of her starts.

Most of the matches on this particular app (I have tried many, including hosting a live dating show with myself as a prize), improbably, were named Daniel. This particular Daniel seemed pretty emblematic of my matches from this app: tall (I’m not sure this app allows guys who are shorter than 6 feet tall?), hardworking, and religiously compatible. He wanted to talk on the phone, which was fine. Much like some of the other suitors, he talked a big game. He also seemed to be trying to figure out if I have sex on the first date without actually asking, which I’ve found is typical.

A sample conversation:

Him: Hey baby, I miss you, send a picture.

SBB: [Rolls eyes as he doesn’t even know me to miss me, sends a picture of self as an actual baby in a bonnet, captioned: “Me as a baby.”]

Baby picture

Him: I mean now.

SBB: [Sends picture of my feet in Adidas socks from Costco, propped up on my coffee table as a I write a curriculum, captioned: “Working hard.”]

Him: You’re funny, Sarah.

SBB: Thank you. Please don’t call me baby. My friends call me Sara Beth.

This Daniel and I talked on the phone two days in a row. He feels really close to me, he sees this going somewhere. He thinks we have a great connection. Would I like to go to his beach house? Interested in meeting his celebri-boss? Do I want him to cook for me? Do I like to see movies? What’s my favorite TV show? His varied heritage meant lots of good food, guilt, and parental involvement. He has a car — want him to drive me somewhere?

I did a fair amount of reflecting and redirecting in my responses. To wit: You seem sweet and fun. I would like to see if I like you in person. Just in case you’re curious, I am not going to sleep with you on the first date. I love when people cook for me, but I’m kosher and mostly vegetarian. Your celebri-boss is also my brother’s celebri-boss, so that isn’t so exciting for me. I like lots of movies, but if you haven’t seen Spaceballs we should hang up right now and you can call me up when you’re done watching your homework, and then we can talk about how Unbreakable Kimmy Schmidt emulates my style. And I have my own, car, actually, and I’ve paid her off and she is hanging out at her country home (my friends’ house) in Westchester.

This was overall a fairly good conversation as [dating app-precipitated] conversations go. We made plans to go out that weekend.

The next morning, my alarm went off, and I jabbed at my phone with the hatred of a thousand burning suns, and then squinted at the screen, sans glasses. My phone was very close to my face when I saw the words of the text: “I hope you can handle me.” I couldn’t make out the picture attached to the text. As I unlocked the phone, I chuckled, and thought: I hope you can handle ME, since I’m a widow and a Jewish educator and a memoirist and a struggling consultant, and, let’s be honest, I just want to get married already.

I opened the text to the full screen, and the photo popped up. I squinted, rotated the phone. What IS that?! I can’t…what am I looking at…? OHMYGOD EW EW EW!

I gasped, locked the phone, tossed it on my bed, and grabbed my glasses.

I AM IN MY THIRTIES AND HE JUST SENT ME A DICK PIC!?

Whilst figuring out how to delete the phallus from my phone and my laptop, I groaned out loud. Once I’d calmed down, albeit only slightly, I replied, “What gave you the impression that I wanted dick pics!?”

He said he thought it was a fun way to get me excited to hook up with him, that he thought I’d enjoy it, and that he’d felt a connection. I wasn’t rude or mean or judgemental, but I decided to push it. I was hoping that his grossness, if handled properly, could stop with me. I asked him what about “she thinks I’m cute and fun to talk to” leads to “I should send her a picture of my erect penis”?

“I had no idea it wasn’t the right thing to do,” he said. “I really thought you were into me,” he said.

A team of friends by my side, I took (dick-free) screenshots of our back-and-forth, asking them what they thought. They advised me how to move forward (don’t), what to say (why bother?), and how to say it (wow, you can’t stop educating, can you?). I found myself educating a (theoretically) grown-up 39-year-old cis-male about why it isn’t OK for him to send, without consent, a picture of a penis — to anybody.

I explained that I don’t, and nobody should, do anything without consent. I explained that when one of my students does something like this, they get sent to the guidance counselor to learn that this is sexual harassment. Unlike him, these teenagers are expected to lack impulse control and sense.

I explained what IS appropriate to send. On text and chat, I send pics of what I’m seeing in front of me, tasty food, or maybe a cool pic from my worldwide travels.

He apologized and I thanked him for that. I also said I couldn’t talk to him anymore.

The rest of the day, I deeply dove into this experience with friends (and a barista). Dick pics are an inexcusable offense, we agreed, but why? I wanted to know why this is a thing that exists in the world we live in today. How is it possible that I’m dating in a time when, for some people, it is customary to get a potential suitor excited with a picture of genitalia?

I talked to my friend from high school, Gabe, who has been dating parallel to me. “Am I missing something, Gabe? You use the apps, too!” (We’re just friends. I like to screenshot when he’s a match for me, and then text it to him and make plans to hash out our dating lives over Thai food, followed by planning to be roommates in 10 years so he can call 911 if I fall in the shower.)

“No,” Gabe agreed with me. “It’s not you, and that’s not normal. I would never do that. It’s not supposed to happen on apps like that. I’m so sorry that happened to you.” He sighed. “It’s akin to assault.”

Jake, a friend who is a gay undergrad, said, “Yeah, it happens on Grindr and some other apps, but that’s really specific.” He looked at me sympathetically. “Straight boys aren’t supposed to do that. How old is he?” I told him. “That’s insane. He is way too old for that!”

My mentor and friend, after discussing a professional project, inquired about my personal life. I told her about the dick pic. She gasped, and then soothed: “I am sure you can find someone better.”

I explained to her about the choices available in my age bracket for dating, a process I have described as “wading in the Gowanus looking for swans.” We’re all messed up in one way or another: widowed at 27, like me. If not widowed, then a sociopath, or divorced, or super-childish, or a mama’s boy, or someone who messes around with psych meds — and illegal drugs — without the support of a medical professional, or some glorious combination of all the above. I told my mentor, sadly, that some days, I’m not sure that I’m going to find someone, better or not, as much as I’d like to. I’m also fighting my you’re-mid-30s-so-just-settle-already urges.

After discussing with more friends from varying backgrounds, we’re all in agreement that a man who is a grown up, has his own job and multiple businesses, should know not to send an unsolicited dick pic. Ever. We also agreed that he was lucky I did him the service of explaining this to him.

After Picgate died down, some time passed. My phone lit up with a call from another guy from the app.

Here I go again.

On my own.

Maybe THIS is the one!

I really hope he doesn’t send a dick pic.

Sara Beth Berman

Sara Beth Berman is a writer and experiential educator living and working in New York City. She is finishing her first book, a memoir about love, loss, and hilarity. Find her on Instagram and Twitter for beautiful realness, educational wonder, occasional rants, and reflections on being an unwedded widow. She used to be a near-professional waterskiier and loves her car more than is probably healthy.