Tangled Web: Couple-on-couple cross-platform courtship

Can we pursue a couple we're interested in via multiple online platforms, or is that creepy?


Jess Zimmerman

Internet Culture

Published Jul 25, 2013   Updated Jun 1, 2021, 10:40 am CDT

Thanks to the Internet, we now have a host of new ways to offend, enrage, misinterpret, creep out, or alienate people. In the Tangled Web, we field your questions about how to be a decent human online. Have a question? Ask [email protected].

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My Salaciously Adventurous Significant Other (SASO) and I have been cavorting in the murky forests of Craigslist casual encounters, looking for naughty fun with other similarly inclined singles, couples, and multiples. Early on in our search, we ran across the ad of a couple who seemed perfectly matched for us. We contacted them but never heard back. C’est la vie—but then a few months later, they responded to OUR ad, expressing excitement at how well matched we seem! We cheered and smiled and responded to them… and again, silence in return. Sadface! 

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That would have been that, except that the universe conspired to attempt to put us in contact one more time, by having one of them show up as a “randomly selected excellent match” in my SASO’s OKCupid account. We definitely don’t want to be pushy or creepy, but spammers and bugs and overly-clever Gmail UI designers have conspired to make email a lot less reliable than it could be, especially when you’re using the Craigslist email relay system and talking about dirty hookup sex from the Internet. So, we’re pondering making one final attempt via OKCupid: “Funny story, you showed up in our OKC quiver not long after we exchanged notes on CL, and we were wondering, did you get our message, or did it get lost in the ether?” Reasonable and forward, creepy and stalkerish, or somewhere in the middle?

Before we go any further, I have to know: Is it possible that you getting together with this couple will be the pivotal event that either allows or prevents the robot apocalypse? Because it certainly seems like different parts of the Internet are fighting to push you together or keep you apart. Craigslist’s email relay (allegedly) trashing your responses, OKCupid making a last-ditch attempt to thwart its wiles … it’s a rivalry as poignant as kaiju vs. Jaegers.

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In this case, I think you get to take another shot at causing Skynet to become self-aware or whatever is at stake here. Craigslist always seems like it’s held together with tape and glue, so I’m not at all surprised if its relay system is constantly dropping messages down black holes, or causing them to get caught in zealous spam filters. And it’s hard enough to find one person you like, let alone a couple; that’s not something you want to risk getting ruined by hinky email.

Even if OKCupid’s match algorithm weren’t on your side, I’d be inclined to think you could get away with shooting them one more email before giving up. Both couples have expressed interest, nobody has said explicitly that they’re not into the idea, you’re all clearly still on the market, and it’s plausible that your prior overtures got lost—that all adds up to making another email sound like a good idea. Conveniently, OKCupid is offering you a way to do it without risking the same problems that may have derailed your earlier communication. 

For the most part, when you’re dating or even trying to make friends, it’s important to learn to realize that no answer is sometimes an answer. You avoid being pushy or creepy by reading between the lines and figuring out when to back off. Or at least, in theory you do that; in practice it’s quite a bit messier and you probably end up scaring some people off and letting others slip through the cracks. But the goal is to be able to understand when someone is sending you a (kinda passive-aggressive) signal with their silence. 

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In this case, though, you’re talking about sexytime with another couple, a situation that will require excellent communication before, during, and after. Because communication is so critical, I think you’re justified in holding them to a higher standard. If they’re not interested, if they’ve changed their minds since contacting you on Craigslist, they should be able to say so explicitly. If they can’t, don’t pursue them—not just to avoid being overly pushy, but because their silence says volumes about how well a liaison would go.

Jess Zimmerman has been making social blunders on the Internet since 1994. Most of her current interpersonal drama takes place on Twitter (@j_zimms).

Photo by born1945/Flickr

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*First Published: Jul 25, 2013, 1:54 pm CDT