The Modern Date: Flirting, Tweets, and Black Lace Panties

Last Wednesday I married the love of my life. This is the short story of some of the things I did before I met her, a guide on flirting using Twitter, Facebook, texting, and sexting face-to-face, in the real world.

Since I came to New York, my romantic life has been a rollercoaster. A very fast one, with 9G turns. If there is a city in the world to flirt and date anywhere and anytime, it's NYC. You don't need the web to meet people. Every cafe, every bar, every party seems like a huge playground for singles to engage in conversations and start love affairs. However, the web can help while you are meeting people and after, all in real time, and face to face.

If you have enough confidence and you are fearless—remember: you have nothing to lose, since you will always have the "no"—any city in the world should be open for the same games. Here are some tips to use technology while meeting people in the real world.

The basic rules

Technology hasn't changed real world flirting. Much. At the end of the day, it all depends on you, how charming you can be, and how much the other person likes you (tip: not everyone has to like you). However, web-based social services like Facebook and Twitter open a door that didn't exist before. They are an opportunity to take the flirting to a new level when you first meet someone in the flesh, all without getting too personal. For some reason, exchanging Twitter or Facebook usernames doesn't seem to be perceived as threatening or serious as exchanging phone numbers or email addresses. After all, Twitter is open and Facebook's friend requests can be denied—or accepted and then canceled.

The web-based flirting can happen right at the moment you meet the other person or later. I remember my first party in the city, hosted by Gawker.tv's Richard Blakeley, a couple of weeks after my arrival. A girl with the most hypnotic cleavage I've ever seen approached me and started to talk. Within a few minutes things started to get fun. A few minutes later, we moved into more suggestive terrain. While this was happening, I saw her Blackberry in her hand. She had her Facebook page open. Without her noticing, I looked her name up in my iPhone's Facebook app as we were talking, and sent her a friend request on the spot. We kept talking and minutes later, when she checked her Facebook again, she found the request, smiled maliciously, and clicked yes saying "I guess we are now friends."

That night was fun.

But it's not always that easy. The key in that example is that it happened naturally, and the move matched the rhythm of the conversation. Taking the step to add someone to Facebook in real time is a risky one, so you have to measure yourself and be ready to gamble. That is the basic rule: Never force things, and learn to read the signs that the other person is giving you. If the conversation is playful, wait until you think is appropriate to incorporate something like Facebook into it.

Tweeting your pants off

Asking for a Twitter name during the conversation is a lot easier than making that Facebook move. After all, Twitter is open to everyone, and direct messaging is a perfect way to flirt—at least for me: I find its 140-character limitation challenging and exciting, and I love when people can be concise and clever in just one single phrase.

Once again, the medium is not important except as a way to reach your counterpart, allowing you to snip casually, responding to the other person's comments. Doing it publicly is a very fine art, which can easily end in disaster, especially if the other person already has a lover. If you have enough wit and you are sensitive to the other person's needs and circumstances, chances are that he or she will be interested in you, and something may happen down the line, as the play factor increases in your exchanges. Sometimes, this game also happens in real time.

One night I met a very pretty—and delightfully nerdy—girl at Delmano, one of my favorite bars here in Williamsburg. She knew Gizmodo and recognized me, so the conversation quickly got into technology. She confessed that she followed me on Twitter, so I asked what her nickname was to add her later. Minutes later, in fact: When she excused herself to the bathroom I sent her the first direct message. After that, we spent the whole night having two conversations, one actually speaking out loud, and the other taunting each with secret tweets. That night was fun too.

For sure, that's also an exception, but it's an example on how Twitter can be a nice way to flirt in real time, as long as you keep it natural and in context, just like you would in a real world conversation.

The next level

Once you have established a Twitter or Facebook beachhead it's time to move it to the next level. You may decide to keep it in the online world, flirting until you feel comfortable to ask for a date. The alternative is to be a little bit more daring, and use Twitter or Facebook to interact with someone you met before, like you may be doing now using text messages. The difference is that Twitter and Facebook are a lot more useful than text messages, because they give you context. For example, you can learn what the other person is doing without asking for it or without the other person explicitly telling you about it.

I used to do that when I was going through my worse digital exhibitionist phase. A couple of times I tweeted or changed my Facebook status saying where I was, and the girl I was flirting with—the nerdy pretty one—sent me messages saying that she was around, wondering if we could hook up for a drink in the most casual way. Likewise, I did the same thing with other people. Of course, this doesn't always work. You or the other person may have other plans in mind. Again, the key here is not to force things, and be as playful and natural as you can.

If you pass the initial filters, and your flirting turns into something a bit more serious, you may get an instant messaging nickname or a telephone number. Instant messaging is not very useful for real time flirting situations. Unlike Twitter or texting which allow you to be cute and playful in a parallel line to the actual conversation, instant messaging runs at a faster pace and requires more attention.

It's only good in two situations. One may be when you are instant messaging with someone else (cue in lots of trips to the bathroom, stress, and a lot of guilt). Two—which is the only one I've practiced—having a sexual conversations in public, in a crowded place in which you can talk into the ear of your lover. This may also happen with Twitter or text messages, but instant messaging—using your favorite program for your smartphone—is my favorite way to do it. But then again, I am really fast typist.

The time it happened it was by chance. She and I started to talk dirty, casually while having dinner in a crowded restaurant, the typical romantic place illuminated only by candlelight and which shall remain nameless because I want to go there again. As our conversation started to get naughtier, we noticed that some people were listening to us, but instead of shutting up, I took out my iPhone and sent her an even racier message using BeejiveIM. Her iPhone vibrated thanks to Beejive's push, she took it out, smiled, and replied back. We kept on talking about other things, with increasing difficulty as the IM conversation got completely explicit and we had a harder time concentrating on actually making sense in our audible conversation. At one point I asked her for something which made her open her eyes wide, giving me that "are you out of your fucking mind?" look of pure disbelief. I grinned and sent her another message. Surprised, she stood up, turned around, and left.

The next time my iPhone buzzed—about a minute later—it didn't have any text. I clicked on the incoming file and a photo of her bare breasts appeared. A few seconds later, another one of her black lace knickers downloaded completely, as she was returning to the table from the bathroom. It ended being another fun night.

That, sexting, could be considered the top level of all these games, but it's not usual to find someone who may want to do it outside a relationship, much less in a real time, face-to-face situations. When it happens, like it did as part of a larger context and conversation, it can be really fun,

Keep your mind open

Of course, things don't always happen in this way. The above is not the norm, but it's not the exception. The fact is that, if the opportunity arises, Twitter, Facebook, IM, or texting could be used as part of the flirting and sexual game not only in the privacy of your home, looking at your computer screen, but anywhere in the "real" world. And I have to say that it's a lot more fun that way.

The irony of all this is that, even while I met my amazing wife through the internet, we never used Facebook or Twitter to flirt. We exchanged a couple of emails, she invited me out for coffee, and the most technology-related thing I did after that was to send her a text message, written as I was running to take the subway:

"It was lovely to meet you. I'm sorry I had to run out so earlier, but I really enjoyed talking to you. Would you like to have a proper date next week?"

She asked me to marry her two months later. And we will live happily ever after.