The Double Message

After a year on Tinder, I realized I might use my time more effectively if I knew more about my date than what could be conveyed in a string of 10 emojis. So I joined OkCupid, and answered questions about my preferred cuddle position, political leanings, tolerance for spicy food, and desire to reproduce.

Unlike on Tinder where I rarely got any messages more elaborate than “hi,” ambitious daters, clearly having read my profile, looked for clever ways to start a conversation. Jennifer’s first message demonstrated that kind of raw ambition, citing to a mishap I referenced under the category: “The Most Embarrassing Thing I’m Willing to Admit.” My disclosed mishap involved urinating all over myself using the “She-Wee”–a device used to pee standing up. Apparently Jennifer had a similar story of woe to share.

A 35-year-old doctor from the east coast, Jennifer looked familiar in that very generic sense. For some reason, I felt underwhelmed by her very well put-together profile. Her photos followed the proscribed formula: hiking photo, dog shot, obligatory body shot, another dog shot, and a picture of her in doctor scrubs looking happy with her co-workers.

Jennifer’s message certainly represented the most clever to date, but even though it caught my attention, I didn’t respond. I had already booked a few dates that week, and didn’t feel like trying to coordinate schedules with a doctor. A day or two passed and Jennifer did the un-thinkable: She “Double Messaged” me.

Jennifer’s Second Message: “I never second-message anyone, but you said [in your profile] ‘life is too short for secrets, hiding the ball, and swallowing emotion’ and I interpreted that as that I should try again and see if I can convince you to have a drink with me. I think we could potentially have some really good and interesting conversations.”

I’ve long debated whether, in the formation of a romantic relationship, it ever makes sense to suffer the indignity of Double Messaging. For those not familiar with the intricacies of modern dating, Double Messaging usually takes place over text or a dating application’s message platform. If you were the last to send a message, the best practice is to wait until the other person picks up the conversation thread again. But in the fast-paced New York City dating scene, that might mean you’ll never hear from your person-of-interest again (until you awkwardly run into them on the train and pretend you didn’t see them). The boldest among us might endeavor to send a second message on the off chance of inviting the person back into your orbit.

Jennifer’s choice to quote back the first line of my profile (about being open and taking emotional risks) stoked my ego in just the right way. Sure, I didn’t interpret my statement to mean I should go out with every person who asks twice, but then, again,  I wanted to reward that kind of dedication to the cause of getting my attention.  I responded.

My first message to Jennifer: “Hi  Jennifer, Whoa. A double message. I’m flattered. And your first message was one of the best (or the best) I’ve ever received on here (I’m new(ish) to this website). I should have rewarded that effort by dignifying your message with a response. And I did really appreciate your first message. . .  Since you did just quote me back about ‘hiding the ball,’ I didn’t write back just because my ‘dance card’ got a little full… So if you can be patient with my scheduling, I’d love to meet up. . .Thanks again for writing twice!”

I figured coordinating the schedules of a doctor and a lawyer might take a month, and I decided I could spare an hour for a woman who had just swallowed her pride for her first Double Message ever. Surprisingly though, Jennifer offered a wide array of time slots and I squeezed her in early the next week.

In terms of logistics, I had told Jennifer that I didn’t want to drink on a weeknight and suggested a walk. Jennifer countered that we could, at least, meet at a bar. She picked a convenient location close to my last meeting of the day.

When I got to the bar, Jennifer had already finished some oysters and half a beer. Although I knew the area, I told her I hadn’t ever noticed this bar before, and apologized that it took me a few minutes to find it. Jennifer responded only: “This is the bar where my parents met for the first time.”  Intense. I also guessed we were not going on a walk, at least for a while. I ordered a glass of wine.

Despite the intense opening, Jennifer had the first date down to a science, inserting cute but impressive stories about her work as a doctor, and also taking the time to ask me personal yet appropriate questions. I found her uncanny ability to quote to my profile and remember fun facts about my life slightly jarring, but, I figured, at least she had done her homework (I really had not).

Given my busy month, I had not focused on the date until the walk over. But, trying to review Jennifer’s profile while searching for the bar had annoyed every other New Yorker on the sidewalk, and had contributed to my slightly tardy arrival. I gave up after making it through the second photo of her posing with her dog.

Next, Jennifer and I exchanged the details of our respective “She-Wee” disasters, each telling the story of that unfortunate time we had managed to spray urine all over ourselves. Her story involved a hike and a wet pair of pants.

My story took place at a Long Island Beer Fest. Even though the event had just started, the bouncer informed me that I could not re-enter if I left to go to the parking lot. Confessing that I had urinated all over myself in a Port-A-Potty,  I managed to negotiate 10 minutes to regroup.

I then painted the colorful and humiliating picture of me sitting in my friend’s parked car with no clothes on below my waist in a very full parking lot. I had attempted to wash and dry my clothes with a bottle of hand sanitizer and a few wet naps—the only tools I found on the floor of her car. Having placed my underwear and pants on the AC vents, the car started to smell of urine and alcohol. Kind of hospital-esque, actually.

The story culminated in an even more graphic depiction of me sobbing in vast Long Island parking lot as passersby observed the spectacle. Running out of time, I called my best friend Cynthia for advice. Having purchased the She-Wee as a gift for me years earlier, Cynthia seemed like the right person to call. Cynthia had advised me to squeeze back into my soggy under garments, leave the event (thus exceeding the bouncer-imposed time limit), and find myself a mall to replace my sullied outfit. Cynthia even helped me negotiate re-entry with the bouncer 40 minutes later.


The cause of my urination humiliation.

As a conscious dating strategy, I almost always bring up the fact that Cynthia is my best friend, platonic soulmate, and the first woman I ever dated. Cynthia lives across the country but my last serious girlfriend cringed at the mere mention of her name. So, in the interest of never “hiding the ball,” I don’t omit Cynthia from stories in which she appears, and let her come up early in any dating situation, even if not by name. Luckily, Jennifer reacted well to my friendship with my first girlfriend, and asked some curious but, again, appropriate questions.

I began to feel a little restless talking about Cynthia (I try not to go too far into my dating past on a first date), and attempted to pivot the conversation. But before I could, Jennifer turned to me and said: “I have something to tell you but first, promise me, you won’t run away.” Okay, I nodded with great uncertainty, looking down to see if my boots were laced up.

“That first girlfriend of yours: what if I told you I know her?  And what if I told you I’ve seen photos of you on social media with her over the last 10 years?

I froze.

“Ok, don’t run away,” Jennifer implored

As I’ve lamented in past posts, the lesbian world is tiny, even between the east and west coast. But Cynthia had done very little dating since our relationship, had visited the east coast one time, and had no friends that met Jennifer’s description. So how?

“Don’t run away,” Jennifer repeated, as she prepared to explain.

Jennifer told me that she had roomed with Cynthia’s childhood best friend, Laura, in college. Incidentally,  Laura had introduced me to Cynthia a decade ago. I searched the recesses of my brain and scrutinized Jennifer’s now increasingly familiar face.

“Wait,” I said.  “Stop.”

My mind began to race and suddenly, I felt like the dumbest person alive.

“You don’t just know my first girlfriend—you had sex with her. You were her first. You’re THAT Jennifer.”

Jennifer nodded, “yes, I’m THAT Jennifer.”

I had been Cynthia’s second lady encounter, and here I was sipping drinks with Cynthia’s first.

The details of this very significant sexual moment in Cynthia’s sexual biography started pouring into my mind, and soon, I realized I knew way too much.

Jennifer confessed that she had followed my relationship with Cynthia (through Laura’s and Cynthia’s social media), had thought I seemed “cool” and wanted to meet me. That charming Double Message strategy about not “hiding the ball” now struck me as highly manipulative.

But Jennifer saw it otherwise: my popping up on OkCupid seemed to hold some kind of cosmic significance for her. Jennifer told me she was tired of dating: “I want to meet my person already.” As she saw it, only a single Double Message stood between her and a lifetime with her “person.” What Jennifer hadn’t stopped to consider was that I was not looking for my “person.”

“Don’t run,” Jennifer repeated a third time.

Double Messaging with Cynthia
Note the 15-hour time lapse between my first two messages to Cynthia. Four hours after I shamefully Double Message, Cynthia responds. After my failure to immediately respond to Cynthia’s first message, Cynthia freaks out and Double Messages me. A Double Double Message

At the end of the date, when Jennifer asked me to go on a second date, I declined politely.  I had stayed put long enough, and now, I did want to run.

But, my refusal prompted Jennifer to make three clearly-prepared counter-arguments:

  • 1) Assuming that my feelings might have been influenced by her disclosure strategy, she protested that her encounter with Cynthia had occurred 15 years ago—a romantic lifetime ago.
  • 2) Further, Jennifer insisted, she deserved credit for telling me about our shared connection up front—”within an hour of meeting” and “not hiding the ball.” She had apparently debated long and hard how to disclose this connection with her friends. Said debate apparently led her to the conclusion that a true upfront disclosure risked my refusing to go out with her at all.
  • 3) Finally, Jennifer argued that we were “on paper” a great match—namely, age appropriate New York professionals with a shared elite educational background. This description of our supposed compatibility proved the biggest turn off of all.

Jennifer had conjured an imagine of me as a person—and even us as a couple—purely through demographic information she had collected on the Internet. OKCupid prompts you to answer questions about nearly every aspect of life, from sexual kinks to overly specific idiosyncratic dating behaviors:

Screen Shot 2018-07-30 at 9.44.12 PM

A sample random question I have yet to answer.

After you answer a few dozen of these questions, OKCupid offers you a “match percentage” with every other potential date on the Internet. So long as both you and your potential match answer the same question, you can compare and contrast answers. By analyzing these hundreds of questions, you could conceivably collect more raw data about a person before ever meeting than you might learn organically in a lifetime.

Exacerbating the situation, Jennifer possessed additional information gleaned through mutual friends on social media over the course of a decade. Evidentially, Jennifer had created a version of me that exists only in the ether.

I’ve come to learn that Internet dating poses a serious risk of investing in the idea of someone without any sense of real life chemistry. To avoid a colossal disappointment on the first date, I try never to indulge in more Internet stalking than is necessary to reassure myself that my date isn’t psycho killer. I definitely do not stalk people’s questions, and try to just trust in the OKCupid algorithm–better to not see how the sausage is made.

But, embarrassingly, during the same week that I met Jennifer, I fell victim to my own little Internet let down. Even if Jennifer’s instinct towards “fate,” supremely turned me off, I came to understand its origins.

Just as Jennifer was busy deceptively Double Messaging me, my very secret college crush appeared on OkCupid as one of my highest matches in New York City. I say “very secret” because, at the time of this crush, I wasn’t even out of to myself. I never interacted with my crush one-on-one. I pretty much just admired her from afar, and thought, perhaps I respected her as a role model (which I’m sure I did).

After contacting her and confessing my college feelings, we actually planned a time to hang out. Because I had been the one to prompt the meet up with my overly bold disclosure, I let College Crush take the lead in terms of where the date might go and how it might end. She walked me towards home (but not all the way…), gave me a warm hug, and said she definitely wanted to see me again.

After she told what she thought I wanted to hear—that we should hang out again—I felt that rush of adrenaline so rarely experienced in the sterility of online matchmaking. And even though I’d like to think I would never have included having a shared “professional background” on my list of compatibilities, like Jennifer, I put College Crush on a present-day pedestal based on nothing more than a high match percentage and a 15-year-old crushette from college.

When I followed up to make a second date, College Crush responded intermittently with tepid enthusiasm (this is called “Frosting”), and then simply stopped responding (this is called “Ghosting”).

My last text put the ball in her court, asking her to let me know when she might be free to hang out again. That was more than two weeks ago. But, at least I know better than to  Double Message her.



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