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

My ex and I broke up a month ago, but we still follow each other on Instagram. He's not on Facebook or Twitter; it's the only social media site he's on, and (other than a few drunk texts from him) the only contact I have with him. When I broke up with him, I said the cliched "I still care about you; I just can't do this" stuff, and I meant it. So I haven't unfollowed him on Instagramwhich I would totally do if he'd dumped meto sort of prove "I care and I'm not totally shunning you." My Instagram is private, and I've let him keep following me for the same "Look, I'm not shutting you out" reason. But I know we'll eventually start dating (and Instagramming) other people, and I don't wanna see OR share that with him. (Plus, he only Instagrams sad drawings he does, not, like, pictures of cats/unicorns.) Should I just cut the Insta-cord now, because it's a pretty bullshit way to show I "care"? Or a harmless way to pseudo-stay in touch?

It doesn’t sound like it’s causing you actual pain to see his sad drawings, which puts it firmly in the “harmless way to pseudo-stay in touch” category for me. If you were getting horrible pangs every time he posted a photo of the inside of someone’s nose, then yeah, you should unfollow—sure, it gives the lie to your claims that you won’t shut him out, but you have to balance that against your own mental health. If this were really hurting you, making you feel regret or jealousy, that would indicate that you’re among the 90 percent of couples who can’t really stay friends after they break up, and it would be better for everyone involved to just give up the charade. (I made that statistic up, obviously—90 percent of the time people say “90 percent” they just mean “a lot as far as I know”—but it’s true that, no matter how good your intentions, a lot of the time when a relationship ends there are just too many extant emotions to have a friendship right away or at all.)

If you’re feeling OK about it for now, though, and are just worried about what might happen in the long term when you both start dating, I’d say you should table that for now. Post-breakup emotions do attenuate over time, and you may feel differently about seeing or sharing by the time there’s someone else in the picture (get it? In the picture? I’ll show myself out). Not to mention the fact that you may find that you’re pretty far into a new thing by the time you actually want to start Instagramming photos of him; I mean, YMMV, but I’ve known lots of couples who get through entire long-term relationships without ever posting pictures of each other on Instagram. Or he could start dating first and you could find that you felt weirdly indifferent about it, or that you felt so keenly about it that you had to unfollow him. (Also, if he were dating a new person, wouldn’t he just post sad drawings of them? That doesn’t sound so bad.) Any number of things could happen by the time you’re past the Rebound Event Horizon and ready to commit to posting photos of someone online.

Basically, as long as it’s not causing you too much tsuris, scrolling past the occasional emo sketch in your Instagram feed sounds like a pretty reasonable price to pay for keeping the lines of potential friendship open with someone you still care about.

If it gets too hard, though, you have my permission to unfollow. He might feel like it’s a little bit of a slap, but uh, not as much as breaking up with him. Most likely he’ll draw a sad picture about it and move on.

I am an artist with an email list of moderate size—like 250 people, most of whom I know. Sometimes someone will sign up after a showing, but usually only after they've spoken with me personally. Sometimes they sign up via a Web interface without having met me, but this is rare.  

After my latest email list announcement, someone whose name I don't recognize sent me a nice but brief response telling me she wished she should come to the show. I don't recognize this name. I don't remember meeting her. Based on the city she entered when she signed up, it's possible I could have met her? But unlikely.

Here's the reason I'm turning this over and over: When I meet people briefly, in person, after a show, and they sign up for a the mailing list, it's not unusual for them to be emotional, or for us to have a conversation that is more tender than usually happens between total strangers. I don't want to alienate someone who has connected with me in this way by responding as if she were a total stranger. And I don't want to creep a stranger out by responding as if she were someone with whom I'd had a meaningful moment.

You are at an uncomfortable threshold of fame: the point where it becomes impossible to treat all your fans as friends. The conventional wisdom is that you can maintain social relationships with around 150 people (though maybe up to 230); more than that and you start needing rules to keep things in check. So you’re essentially just moving from being a person who does art for her friends to being a person with a fanbase.

This is a position that will be familiar to anyone who’s had a moderately popular blog or Twitter stream. You’re going along happily chatting into the ether as though you’re talking to your bestest buds, and then someone chats happily back who you’ve never heard of before. (Or, if you’re unlucky, someone randomly flings poo at you—it is the internet, after all.) Even when the commentary is positive and friendly, it can be disorienting. It’s like talking to yourself and having someone answer.

Anyway, as a person who has now exceeded the number of fans she can realistically maintain stable social relationships with, you are not expected or required to recall the circumstances of every meeting (if there was one). It is time to put aside your anxiety about how well you should remember this particular individual and start developing a reliable “gracious host” tone for use in correspondence. The idea is to sound warm without being familiar: Imagine you are hosting a very large, elaborate soiree and somebody’s plus-one has approached you to say what a lovely time she had. You want to strike a tone that contains none of the “who the eff are you” that you are undoubtedly feeling at that moment but also acknowledges that there are 250 people at this party and you are not bosom friends with each of them.

Accordingly, I recommend something like “Thank you. If only we could have more shows!” (Subtext: “yes, it would be great if I could art everyone in exchange for money, but I do not have nor need I have feelings on whether you individually are able to attend.”)

Eventually, as you get more practice with that tone and get comfortable with the idea that you don’t need to be personally close with all your fans, it will become natural.

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

Illustration by Jason Reed