3 Tips for Moving Online Dating Encounters to Real Life

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A friend recently asked me to check out his online dating profile. He’d been on the site for months, but so far wasn’t having much luck and hoped I could help pinpoint why. I scanned his profile and couldn’t help but smile. For someone who knows him as the witty, wry man he is, his profile reads hilarious. But to a stranger, his jokes about being a hobby arsonist and profile picture with his handsome, Clooney-bearded face covered by the head of his bushy tabby could appear anywhere from strange to borderline psychotic. Alas, another victim to the black hole of botched communication that is online dating.

Maybe your profile isn’t the problem. Perhaps it’s perfectly polished and yet, when you finally meet that match in person, the mood is staler than four-day-old donuts. It doesn’t matter how witty your OKCupid repartee skills are; when you finally meet in person and your chemistry is flat, you can’t help but feel like you’ve wasted the past two weeks of internet flirting.

Finding success with online dating often takes a delicate combination of digital and real-life charm. You must be appealing in that initial back-and-forth and also confident enough to set up and actually attend a real-life meeting. There is a very real gap between connecting online and connecting in real life. Studies have shown that only 10 percent of app matches lead to real dates, and before achieving that small fraction, you must first exert a substantial amount of effort messaging back-and-forth.

All of that effort for something that has such a slim chance of actually working out has many users asking, can’t there be a compromise?

Recently I chatted with the founder of Whim, a San Francisco-based dating app that sets users up on real dates within a one week window, offering an interesting combo of online and real-time dating that serves users who crave a faster real-time connection.

Founder Eve Peters hopes that Whim will act as the ultimate compromise between digital dating and a quality face-time connection. “It takes the best aspects of what digital offers to us—the ability to sort, filter and target the people that interest you—and combines it with the in-person emphasis of a real-life date setup service,” comments Peters. Users tell the app what they like to do and when they are free, and then they set out searching through profiles and flagging the ones they would be interested in dating. When users show mutual interest in one another, the app takes over the scheduling.

Of course, Whim is not the first of its kind. Online app How About We was based completely around the concept of getting people off their phones and out on dates, even offering a “TONIGHT” feature that gets users face-to-face that very night.

But, according to Peters, other apps still haven’t made getting from phone to date very easy—users are still bogged down by logistics. Peters, who spent time working in an OKCupid Lab before founding Whim, likens her app to a personal assistant; When there’s a match, Whim takes over and schedules a date for you, from time to suggested location. The app also connects you with your match so you can discuss further logistics or engage in optional flirty chit-chat, but it’s not necessary.

But are Whim users forging meaningful relationships or just meeting up in hopes of getting down? Apps like Tinder, Grindr and OKCupid are notorious propagators of hook-up culture, with many users trolling more for a fling than a full-time partner. This can make those who are searching for something more meaningful feel as if their time is wasted, leading to frustration and quite possibly a healthy serving of hurt feelings.

“The fact that [Whim] sets up actual dates at nearby locations and requires carving out time from your schedule in advance, somewhat deters those only looking to quickly hook up,” Peters explains. Of course, the opposite could be argued: Finding someone who can meet you tonight without putting in the effort of a back-and-forth digital courtship could actually make it easier for those to hit it and run. Still in the early stages of use, only time will tell how many users are finding a lasting connection.

3 Tips to Finding A Compromise Between Digital and Real Time Dating

Meet faster.

I have an aunt who is a self-proclaimed online dating expert, and she has created a formula for sussing out a potential match. It looks like this: One day of messaging, one short phone conversation, and if those go well, one date scheduled as soon as possible. Many online daters tend to drag out the digital interaction, trying to gauge interest and connection. But meeting for a one hour dinner or drink can tell you much more about a person than two weeks of OKCupid chit chat. The next time you’re engaged in a witty exchange, suggest you finish the conversation over dinner the next night.

Get off the app and on the phone.

It’s understandable why you would want to engage in back and forth chit chatter before meeting face-to-face with a stranger. However, moving quickly from messaging to an actual phone conversation can help evaluate your connection before you decide if it’s worth it to meet in person. While older generations who are dating online tend to jump onto the phone with ease, millennials—who were practically raised by the text message—often find phone conversations uncomfortable and avoid them. Does the conversation flow easily? Do you find them engaging? Do you like the sound of their voice (this is more important than you think!). To avoid wasting either of your time, limit the calls to one thirty minute conversation before making a real life date.

Don’t over-exaggerate your personality.

Most online daters spend a ton of time finessing their profile, which makes sense – it’s what potential matches will judge you by. However, laboring over sounding extra smart or sassy on your profile or initial correspondence can hinder your success. It could either seem off-putting out of context (remember the sarcastic cat-bearding friend I mentioned earlier?) or lead to a let down when your date meets you in person and you’re not as hilarious or clever as you seemed initially. Keep your profile sincere and your in-person connections will be as well.

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