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Troubleshooting a First (Online) Date

Knock it out of the park with these five first date tips.
Troubleshooting a First (Online) Date

We call it online dating, but that’s a misnomer. It’s really online meeting. That first date, for better or for worse, must happen IRL, in real life. Sure, it’s about the clicking and the picking, and there’s definitely a trick to that (and it has nothing to do with profile pictures—seriously). But that’s the easy part. It’s also about the meeting and greeting: How should you ask her? Where should you go? What should you watch out for? (Hint: Don’t go for a walk in the park!)

There’s a reason we live in a Tinder world. After years of encouraging long profiles, dating sites have learned something: Many daters make decisions based solely, or mostly, on photos. And if all you want to do is sleep with the hottest girl on OkCupid, that’s cool.

But if you want to date someone you can be vertical with for more than five minutes without getting a headache, try this: Search for keywords first. For example, if you love cycling, write every girl whose profile mentions that. There’s a lesser chance she’ll look like Giselle, but a greater chance she’ll be cool as hell.

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Most of you won’t follow this rule, since talking to a person you’ve never met is pointless when a first date can be arranged so much more efficiently online, right?

Wrong. After a few messages, the smart dater gets a number and calls. Why? First, you set yourself apart from the pack. With texting making us lazy and monosyllabic—“U want 2 meet 4 beer? ;)”—a good woman will be thrilled by this old-school flourish.

Second, and most important, a call reveals red flags messages can’t. Suffering through a few minutes of weirdness on the phone beats wasting time on a date you could’ve canceled had you done your due diligence.

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This rule isn’t unique to online dating. But if you are doing the digital thing, there’s a good chance you’re going on a lot of dates. With so many opportunities, it’s easy to let manners slide.

But if you’re serious about finding someone, not just sleeping with a lot of people, never cancel, reschedule, or show up late without a rock-solid reason.

Taking a relaxed approach to meeting doesn’t make you seem aloof or cool or in demand. “He’s so undependable, it really turns me on!” said no woman ever.

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Dinner with a first online date is a rookie move. Ordering? Waiting? Eating? Paying? Too much time and pressure. Instead, meet for a drink or just coffee. (A real man doesn’t need alcohol to talk to a woman.) Keep it short and sweet, and then wrap on a high note.

The crucial part of a first date is sitting down, face-to-face, without intrusion. Live events—music or comedy—become weird. You’re not really watching or talking.

Ditto a walk in the park. It seems like a good idea, but the context is all wrong: A premature aura of romance creates distance. Plus, walking raises too many questions: Where do we go? When do we stop? Am I being judged on my intersection etiquette?

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An hour flies by. You laugh at the same stuff. Her smile’s killer. Everything else looks good, too. Now what?

Online dating is notorious for “first-date intimacy.” Seek a quickie and you shall find it. But if you’re looking for something more, do this: Tell her you enjoyed yourself and want to see her again, kiss her on the cheek, and walk away. Do not lock lips. Do not invite her home. Remember: What starts quickly ends quickly.

So step away from the hottie. It’ll take willpower, but first meets are about sending the right message. If she’s relationship material, she’ll admire the restraint. And some tension will flow beneath the surface of that second date, and the first kiss will be fireworks.

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