From Online to In-Person: Navigating the First Date

How to take the conversation from the web to face-to-face.

It's always your best bet to take your Internet conversation into the real world as soon as possible before you establish a virtual rapport that can become awkward and stilted when it has to translate into face-to-face. So, if you've exchanged a couple flirtatious messages with a potential mate, established a basic foundation of things you have in common and are somewhat assured that it's worth testing the waters with a meet-up, take the plunge and ask her to hang out.

First meetings, especially those catalyzed on the Internet don’t have to be complicated, but there are a few caveats to heed prior to jumping in. To have the best possible time, while preserving your physical and mental wellbeing, read on.

Remember that getting ready for a first ‘meet-up’ takes as much time and effort for a woman as a real first date,” Davidson explains. “She’ll spend time doing her hair, applying her makeup oh-so-perfectly, choosing the right outfit—all of which is easily an hour or more out of her day. You won’t be spending the same amount of prep time, so consider that her investment has already trumped yours, and make it worth her while.”  

Davidson suggests that you meet somewhere that you’d take a “real” first date, not just a “check-her-out” prospect. “You needn’t go so far as to spring for dinner, but a drink in a nice environment, or even lunch, will make a far better impression than coffee at the local Starbucks,” she says. “By treating her with respect, picking up the check, and in general being cool, you’ll win points. Granted, if you two don’t click, they might just be karma points, but if there’s chemistry, you’ll have avoided turning her off by lacking finesse.” 

Most online dating advice regarding safety is geared toward women, and not without good reason. Sexual predators constantly troll the Internet looking for prey, and ladies who trust too easily can, and do, wind up in compromising or even dangerous situations.

Women are told to A) Meet their date in a public, B) Let someone know where they'll be and with whom, C) Bring a cell phone, and D) Have an exit strategy. Think about that for a minute. No matter how hot you are for her, or how hot she seems to be for you online, in person, the first thing she’s going to try to suss out is whether or not you’re to be trusted. It’s no reflection on you, and it doesn't matter if you spend your Sundays helping out at the local orphanage or old folks home. So if she's being a little less forthcoming with personal information or unwilling to go somewhere more private, she’s exercising common sense. Let her, and also bear in mind that common sense works both ways—the aforementioned cautions all hold merit, for her as well as for you.

One of the biggest mistakes of online communication is thinking a relationship forged from over-sharing is the real deal. There’s always the chance that the person you got to know online isn’t what she seems. Men aren’t the only predators hunting for their next mark or broken toys searching for someone who can “fix them.” If your date is too eager too soon, or seems a little too interested in your personal finances, or for some reason just makes the hair on your arms stand up—and not in a good way—it’s best to proceed with caution, if at all.

“If someone starts talking about the future at the first meeting, or even if she jumps into bed with [you] the same night (unless it was a sex match-up site), be on the lookout for a clingy, dependent type,” Davidson warns. “Also watch the type of questions she asks. Some information will be designed to ensure her own safety; other information is just inappropriate—like discussing or asking about intimate details of past relationships early on. Usually, if something feels ‘weird’ or ‘off,’ it probably is, so trust your instincts.”

Finally, Davidson notes, guys should avoid getting so wrapped up in their own fantasies about someone that they miss the cues that would otherwise tell them she’s not right for them. “Sometimes we are our own worst enemies in that when our hopes and fantasies clash with reality, we tend to over-focus on the fantasy and make excuses for or rationalize the reality,” she explains.  “Men are just as prone to this as women. I’d advise the same degree of self-awareness that I’d suggest to women in order to avoid the mess that can ensue as a result.”

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