photo by derek powazek

The Flirty Medium

Derek Powazek
Fertile Medium


In this special Valentine’s Day edition, we tackle online flirting from two different perspectives.

How should you react when you suspect the guy you’re dating is flirting with other women on Twitter?
– Anonymous 1

My boyfriend doesn’t want to “play” on Twitter. Why is he being such a grump?
– Anonymous 2

I remember the first relationship I had that started with flirting online. I was shy, and this new digital world gave me a chance to show off a bit. I like to think that those witty late-night e-mails helped me form a relationship with a girl I otherwise would have never had a chance with.

We dated for a while. She was crazy. So was I. It was great. But I always felt that we were somehow more honest in e-mail. We were both writers, and establishing our relationship digitally let us be more our true selves. Our real-life dates would be followed by far more intimate digital conversations. Giving that intimacy a place to live outside of our in-person communication had the side effect of allowing us to be less than totally honest in person.

This digital world we’re creating is an enormous gift to those of us who might not feel totally comfortable expressing ourselves when real, live eyes are focused on us. The screen is a shield. Some say that this is isolating, but in my experience, it’s the opposite. We get to learn how to express ourselves in a safe space before trying it in person.

Our two anonymous callers are both grappling with the complexities of online flirtations. In one case, the caller wants more digital intimacy from their partner. In the other, the caller is threatened by the intimacy their partner seems to share with others online.

In both cases, the real issue is what kind of boundaries have been established in the relationship. The boyfriend who is flirty with others online may have established their relationship with the caller by being flirty online. Now in a real-life relationship, his flirting with others may be a valid concern (is he shopping for his next relationship?). Then again, maybe the caller needs to acknowledge that the guy is just a flirt and find a way to be okay with this. Perhaps the way to keep his attention is to restart the flirting that established the relationship. If he’s flirty on Twitter, flirt with him there! It’ll also serve as a subtle reminder that his flirtations with others are visible to you.

As for Anonymous 2, whose boyfriend has said he doesn’t want to “play” on Twitter, well, that’s some clear communication right there. You’re in a real-life relationship, and he’s setting clear boundaries about where his comfort level is, so you’ve got to respect that.

But perhaps there’s a middle ground. If his discomfort lies in the public nature of Twitter (assuming that you two have public accounts), then maybe you can flirt in more private ways. You could each register additional private accounts and send your flirts privately. Just remember to make sure you’re using the account you think you’re using (ask Anthony Weiner). There are apps designed just for this. Couple is especially nice—I’ve used it with my wife when we’re away from each other, and it’s fun.

Remember, you have a real relationship with this person, and that’s more important than any of this digital noise. When Twitter is down, you’ll still have each other. And that’s what every online flirt really wants.

Got a question or comment about living online? Send your flirty tweets to @fertilemedium or call (415) 286-5446 and leave a message.

This column originally appeared in A List Apart on 14 February 2013.

This is Fertile Medium, an advice column for people who live online. Each edition, I’ll take a question from you about living in and building social spaces online, and do my best to answer. Want to ask a question? Tweet to @fertilemedium or call (415) 286-5446 and leave a message.



Derek Powazek
Fertile Medium

Digital community, analog farming. Social media design, photos of goats and chickens. Author of "Design for Community," teller of stories. Mostly harmless.