Hi! How are you? Can I just say how much I love your column?
Now that the sucking up is taken care of: Jono, I have a boy problem, but I don't have a crush on this one. Ya see, I was a pretty happy collegiate loner when I reconnected with a guy we'll call Loki (we had a two-semester class freshman year but hadn't spoken since). Well this year we've tentatively begun a friendship (lonerdom is great, but I thought it would be nice to hang out with other humans again). One-on-one we usually have a good rapport, but whenever we're with Loki's group of (entirely female) friends it's not so easy. I'm introverted, awkward, and take great pains not to inflict too much of my awkwardness on others. So I have a hard time breaking into the inside-joke heavy conversations they all engage in. A few of his friends are good about giving me openings so I don't just sit there staring at my phone the whole time, but two of them are really busy and the other just transferred. Loki himself just says things like, "Are you following this conversation at all?" and,"We're not excluding you on purpose, I promise." I'm not sure if they're all just as awkward as me (which is possible since everyone in this situation, including me, is a nerd) or they're just not interested in adding me to the group (also possible; this is girls at a tiny school we're talking about, not to mention that one literally chose to read rather than talk to me when we were left alone). One thing I've learned from The Walking Dead is that people tend to find silent females a bit off-putting, but I'm not doing it on purpose. I would love to join their conversations, but I think laughing at jokes I don't get or stopping someone's hilarious story to ask for context just makes things more awkward. I could theoretically remedy this by hanging out with just Loki, but he used to have a crush on me and I don't want to seem like I'm leading him on by asking for a solo hangout. Basically I'm asking for tips on how to break into an established friend group, or how to tell when that just isn't going to happen. And if the second one is true, how do I hang out with Loki one-on-one without him thinking I'm crushing on him?
P.S. I feel I should mention that Loki and I aren't BFFs, more like MTALTFs (more-than-acquaintances-less-than-friends).
P.P.S. Loki has developed a habit of asking why I'm so quiet, was I always like this, etc. and it's getting annoying. How can I tell him to drop it without coming off as oversensitive and/or rude?
Loki, the Trickster God? Don't trust that dude! I mean, you can hang out with him if you want, but he is the father of Fenrir and Jörmungandr the World-Serpent. So... watch out for that.
I wound up in situations like this when I was in high school. I hadn't gone to the same middle school as everyone else, so even during freshman year, most people still knew each other and could find some common ground, while I just wandered around inventing new and exciting ways to not talk ever. By the time I could actually bring myself to say words at people, they'd all formed their core friend groups. So even if I did make some close friends here and there, as soon as they all hung out together, I was pretty useless; at best, I was like a one-liner robot, who could make exactly one funny observation and then power down for the evening. So I sympathize with your situation.
For the record, I think Loki's attempt at nagging you into being talkative is 100% earnest; he's just not very good at it. A lot of outgoing people are literally not capable of understanding shy people; they will take you aside and say "I have an idea! You should just open your mouth and say a bunch of cool and awesome stuff that will make you sexy and popular!" and then pat you on the back, confident that they have resolved your problem. Or they'll single you out in mid-conversation and be like "Hey sadbrain! Say somethin'!" and of course you will be like "mrrhn hrnm hmm" and hide behind a shrub. I think Loki is honestly trying to be helpful; he thinks you're gonna go "Ohhhh, I should be not shy! Okay!" because this hasn't occurred to you yet. There's really no subtle way to address this except to tell him (when you two are alone) that it's not helpful.
With all that in mind, here are some ways to try to integrate yourself into this group. I think most people can integrate into any group, no matter how established, if there aren't any serious personality conflicts involved, but my experience is with groups of dudes; I practically need a diagram to understand how your gender works, so I'm not promising anything.
Carve out a niche wherever possible.
I have some (now) close friends who met each other when they were, like, zero. Their in-jokes are so ingrained that they won't even have to say them out loud half the time, so for a while, our friendship consisted of them essentially talking in code while I stood there thinking "Question marks??" But I gradually worked my way into their group anyway, simply by being around them long enough that I found the time to tell my own stories of total disaster and walking into things. Eventually we'd all learned enough about each other that I never felt left out. Since you asked how to tell when you're not going to fit in, I'd say there's no time limit, but there is an interaction limit. If you slouch in the background of every conversation like a sad mime, fitting in may very well take forever, because nobody knows anything about you. If you repeatedly make the attempt and everyone's still sort of ignoring you, then there's a good chance you're just not compatible.
Have some one-on-one conversations.
First of all, give the book-reading girl who ignored you the benefit of the doubt, and assume that she's just super-awkward rather than horrible. If you give her another chance, the worst-case scenario is that she turns out to be horrible, which you already suspect, and nothing is lost. With that in mind, college is one of the easiest settings in the world to strike up a one-on one conversation with someone; you can talk dorms, classes, where you're from, professors, whatever. All of these are good conversation-starters that don't sound forced or awkward, and no functional human being is going to respond to "How are your classes?" with "Remember the time my friend Dwayne got bit by a zebra? LOL!" and stare at you expectantly. You can try to have these conversations when you're part of a group that's a little more dispersed, or when you see any of these folks around campus; the point is just to have at least one or two people you're more comfortable talking to.
Invite people over.
I know this is a daunting suggestion for a shy person, but I'm not talking about a crazy house party or anything; just to watch a movie or eat something you baked or whatever. If you're living in a worst-case scenario (no kitchen, no TV, no room), order pizza and find an open space you can use. Make Loki your go-between if you don't want to invite people yourself. The idea is just to be the host of something, because you're socially obligated to talk to your host, and if you go off into the corner and tell inside jokes instead, you are basically awful.
The TLDR here is this: You should make the effort to get to know these people one-on-one, or on your terms, but if they keep excluding you, you're not obligated to keep trying; there are other people to be friends with, even at a tiny school. Oh, and you're right to worry about leading Loki on; don't take him shopping with you for sexy underwear, or he will bring about Ragnarok, the end of the world. If you do hang out with him alone, be sure to call him "dude" and say tremendously unsexy things. Mention how important your friendship is, and refer to him constantly as a friend. As long as you're not being huggy or flirty or whatever, he should get the idea (just be absolutely clear that you're not interested in a relationship if it ever comes up explicitly).