I first tried online dating in the fall of 2001. I was a freshman in college and had quickly determined there were few suitable matches for me at my Southern liberal arts school, so I joined a new site called Match.com. In 2001, my model for online dating was based on the email correspondence in “You’ve Got Mail,” so I took to writing missives to my matches, delving into the nuances of my musical preferences and the complications of my extended family in equal measure.
Over the next 15 years I kept coming back to online dating, trying out most of the major platforms in succession: Match, eHarmony, OkCupid, HowAboutWe, Tinder, Bumble, Hinge, Happn. The appeal of meeting people outside my tightly knit social and professional circles always outweighed the slog of wading through pools of strangers, hoping to find the one perfect fit.
Over time, the rules of online dating shifted, especially when the swiping apps came on the scene. Long emails back and forth gave way to “hey” and carefully considered profiles morphed into a series of photos that ranged from blurry to the ill-conceived bathroom selfie.
By the time I returned to online dating in early 2016 I was feeling demoralized. Dating apps seemed to be more about playing a game than discovering mutual attraction.
Desirability algorithms determined who you saw (and who saw you) so that an “8” would never be forced to consider a “5.” Delta Airlines ran a promotion where people could take a photo in front of a mural of a distant location, so as to appear worldly and well-traveled (instead of, you know, actually traveling there). And the experience for most women included receiving sexually explicit messages and photos, as well as insults and threats of violence when their potential paramours felt rejected. The whole thing had become a chore.
Based on my successful career in sales, marketing and startups, I devised a system to optimize pipeline throughput time and minimize false negatives. That is, a process to weed the wrong people out as quickly as possible while not eliminating great people I might otherwise overlook. (Note: This system was specifically designed to lead to a relationship. If that’s not your goal—perhaps you’d like a series of one-night stands—then this is probably not the best advice for you. But hey, no judgment. You do you.)
1. Choose the right platform
There are two things to consider when deciding where to set up a dating profile: 1) is this the demographic I’m looking for; and 2) does the user experience (UX) create the right environment and incentives for success?
Each of the platforms have different communities and expectations. Match and eHarmony tend to be much more marriage focused. Tinder has a well-earned reputation for hookups and playing the game (i.e. swiping with no intent of ever meeting up). OkCupid tends to attract creatives, entrepreneurs and a slightly younger (20s-40s) demographic, in my experience. Knowing where you fit is the first step toward aligning expectations and increasing qualified leads.
The second thing to consider is the platform’s UX. A profile that is mostly photos with space for a small amount of unstructured text (like Tinder and Bumble) is going to lead to matches mostly based on physical attraction. (Research shows that the majority of Tinder profiles use fewer than 100 characters in their bio, with 36 percent entering nothing at all.) Similarly, a swiping functionality that doesn’t allow you to see anyone else until you decide on the profile at hand, will lead to quicker decisions on more profiles. (Fun fact: The dopamine rush you get from swiping has been compared to the rush you get from rewards and drugs.) Conversely, a platform that emphasizes a personal narrative or asks questions to uncover values gives a dater more data and context to make an affirmative decision.
Personally, I prefer to have writing samples when presenting my profile and evaluating a potential match, which is why I chose OkCupid when I went back online.
2. Show, don’t tell, in your profile
In the past I had made the mistake of writing profile copy that sounded more like a resume than a personal introduction. I’m proud of my professional achievements but it often came across as bragging and one-dimensional. So this time I structured my personal narrative around a top 10 list of things you should know about me. It was a strategic mix of 40 percent professional, 20 percent side hustles/hobbies, 10 percent random facts that borderline on quirky, and 30 percent authentic personal insights.
Similarly, my photos were curated to tell a consistent story, including activities, full-body shots and shots with natural makeup. Each picture was selected to add something to the narrative. Pictures playing cello and trekking in the Himalayas made the cut. Photos with my nephews and group shots with friends who looked like me (making it hard to pick me out) were excluded. (Pro tip: Photos can be dropped into Google Image Search and located on public social media profiles, so if you don’t want potential matches to figure out who you are, don’t use images you’ve posted to social media – or make your accounts private while you’re online dating.)
The goal overall was to show, not tell.
3. Create a high bar for incoming messages
An analysis of my online dating efforts over the last fifteen years revealed that the response rate to a message where I made the first move was less than 10 percent, and of those responses only one in five led to a date. Instead of investing effort into improving the response rate to my outbound emails, I decided to save my time for responding to incoming messages.
Of course, any woman who has spent more than an hour online can tell you that the experience can be quite jarring. So I created a strict filter for incoming messages to make it easy to cut through the noise (and filth). In my process, a message had to meet the following criteria to earn a response:
1. It must be in complete sentences and use appropriate spelling and grammar. Classic autocorrect typos are forgiven; major lapses in written communication skills are not.
2. It must reference something in my profile. If your first attempt could be copied and pasted to every woman on the site, it won’t make the cut.
3. It may not include sexual content in written or photographic form. No innuendo. No “jokes.” Nothing.
Any message that didn’t pass this filter was immediately deleted and that user was blocked. This might seem like a low bar, but of the 210 messages I received over a two-month period, only 14 percent of them made the cut.
4. Respond to everyone who makes it past that filter, even if they’re not “your type”
In the past I had a pretty strict sense of what my “type” was—tall, smart, well-traveled, and multidisciplinary with at least one graduate degree. Those attributes are pretty easy to check for in a dating profile. Unfortunately, they weren’t the values most relevant to a healthy relationship. What I most cared about was kindness, curiosity, self-awareness, empathy, and purpose, which are much easier to deduce in person. So I decided to respond to everyone who made it past my filter and expedite the online communication process in order to meet up as soon as possible.
Of the 29 messages who made it past my filter, only 52 percent (15) responded after I wrote them once.
5. Meet them IRL as soon as possible by going on a “0th date”
My goal was to meet dates in person as quickly as possible, but previous experience (and research) told me that I would know within the first five minutes whether or not I wanted to spend more time with them. So I didn’t want to commit to a full evening of dinner or drinks, which is what prompted me to create the 0th date. It’s the pre-date before the first date that I limited to one drink and one hour. The question I needed to answer was, “Would I like to get dinner with this person?” (Not, “Is this the one?” or, “Can I see myself having a family with them?” Just, “Are they interesting enough to commit to a full evening with them?”)
I would tell my dates that I had a hard stop—whether for dinner with friends or a late conference call with Asia or an early morning appointment—but that I would love to meet them for a quick drink. I figured it was one way to cut down on the calories and cost of dating and minimize the amount of time I had to downshift into storyteller mode because there was no spark.
Asking them out was also one way to show them my personality given that I ceded the first move. I’m pretty forward and ask for what I want, and not everyone is into that. So it was no surprise that of the 15 men who responded to my first message, only 40 percent (6) affirmatively replied after I asked them out in the second or third message.
6. Don’t let dating consume your life
When I went back to actively dating I promised myself it wouldn’t take over my life. I am a busy woman, with a demanding job, wonderful friends, several side hustles, and a regular fitness regimen, and I didn’t want dating to feel like a chore. So I decided to limit my dates to one night a week, and stack them back-to-back. I already did that for networking events and coffee chats so why not 0th dates? I picked Wednesday and scheduled a 5:30, 7:45, and 9 pm dates, choosing different neighborhoods that were easily accessible by subway so as to avoid Charlotte’s fate when she double booked.
7. Throw all of the rules out the window if they aren’t serving you
On my second of these 0th dates (7:45 pm, a flask of whiskey, and a walk on the Brooklyn Heights promenade) I met my boyfriend. I knew within minutes that this guy was special, and threw my entire playbook out the window. Our 0th date seamlessly transitioned into a first date and six hours later he was kissing me on my stoop, asking to see me again. Over a year later, we’re still going strong. And yes, he knows there was another 0th date before him that night.