Telling stuff about the setting and the basics of the first EP would be a great place to start. The manga is also a great to ease into the story, though it also adds more to the story in the latter arcs so to experience the whole story.
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I usually tell them there’s witches who are cool and a guy who cries and it’s a murder mystery. Unfortunately, though, a lot of them lose interest due to EP1 only having the murder mystery aspect until the end, even with my telling them “it gets less family drama and more fantasy later on.” One friend got interested through a lot of the full spoilers in Chiru. But most people I know really only want the witches since I on and off role play as Beatrice on tumblr (well an AU version).
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Hmm, I think spoilers definitely shouldn’t be said for the most part, but like one of you has suggested, some should be said to get somebody into Umineko, especially cause the first few episodes have rather slow pacing and whilst it is interesting, it may be dull for some. For me, it’s completely fine if say, 50% of Episode 1 is spoiled. Of course, some will lose interest if they’re spoiled like that, but the events of Episode 1 set the basis for the story, so I think to spoil somebody with a few aspects about it is a requisite to get them into Umineko. Though I’m saying that just the main events of Episode 1 should be said rather than details, of course. And whilst you should keep our beloved Beato’s existence ambivalent, I think it’s better to assure somebody new to Umineko that she will appear at some point,cause her existence itself is one of the main plot points in Umineko, and that should keep somebody interested in the series. After Episode 1, you can just hint at things vaguely of course, like hint vaguely at some clues before they start each episode or something, but frankly, if somebody gets interested in Umineko I don’t think they’d want any spoilers.
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I’ve convinced a few friends to play just through the soundtrack. It’s not even hyperbole to say it’s one of the greatest OSTs in all of gaming, and usually showing them goldenslaughterer, hope, or mirage coordinator is enough to get them to at least try it out (esp when you say that there are 200 tracks, with at least 50 on par with those)
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I can’t speak as someone who has gotten anyone into Umineko simply because I never have, but I can tell you a bit about how my best friend got me into the series.
I actually began reading because I wanted to better understand my best friend and a character from the series that she is connected to. I wanted to be able to talk with her about her interests without getting so confused. She told me a bit about Umineko and I honestly wasn’t interested in it at all. But, like I said, I wanted to better understand her and the character she feels so close to. So I began reading. And after a while, I fell in love with it myself.
Sometimes all it takes is a desire to understand someone and be able to talk to them freely about what interests them. At least, that’s what did it for me.
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This is more of a vent topic, as I feel fairly frustrated with my mostly unsuccessful attempts to get people to read Umineko. So I would like to hear everyone else’s successes, failures and experiences. Allow me to start with my own
8 Friends that I regularly game with
Tried to sell Umineko over Vent once
1 took the bullet (in exchange I promised to read the VN he wanted to discuss). He loved it
My best friend
Tried to convince by phone multiple times
Read EP1 then rage quited
2 Work friends
Found out they “read” as a hobby. Bought them the Question Arc for their birthdays
Haven’t got to dinner in EP1 after 3 months in reality. Egging them on every other week right now…
(Started my third re-read around that time hoping to discuss with them. EP6 now… with super slow 20h per novel speed)
Best Friend’s Wife
Work in progress, might need a little more persuasion
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I got two people to read it. One is still in game 1 and the other is in the middle of game 2. I’m content right now.
I have never gotten any of my IRL friends to read it, but I did manage to get two of my online friends to read it. One of them pretty much got into VNs because of me, and is currently on episode 6. The other just finished recently, and loved it so much, her twitter account is now Umineko themed. The latter friend is now reading the manga.
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I’ve managed to get someone of my family into Umineko (and Higurashi as well), but I have to act as a translator for now. We’re going sooo slowly that it’s kind of discouraging, I think it’s been almost a year now and we’ve managed to stop at the end of the first day of EP2. This is also due to the fact that it isn’t easy to really get some hours together without any distraction in order to concentrate on the story, and so there are always huge gaps between each reading session. So, even though I can tell they’ve taken an interest in the story, I think it’s best if we stop reading together at the end of EP2 and they’ll see for themselves if they have the motivation to keep on reading, because I think it’s essential to have it in order to really immerse yourself into the story (especially for a story like Umineko I mean). Still, we’ve got some interesting discussions reading together and I like the experience, but due to context I’d prefer they can really dive into the story without such breaks, even if that means doing it alone. And, no matter what they may believe, I know the language barrier can be easily overcome, the only thing they lack is confidence. The rest will naturally follow.
That’s an interesting topic and it makes me really wonder about what I should do. I guess I’ll have to talk more about this with this person even though I’ve already tried to a little.
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My circle of friends consists of mostly very busy people who enjoy working on their own thing or just get easily distracted. And if I have friends who are not busy, they either are very squeamish about gore or horror shenanigans or they really can’t get into VNs. So most of my attempts probably come off as annoying.
I did manage to get one friend into Umineko. I sold him with the mention of how fantastic the music was. And he likes music a lot in general. He finished reading and every time Umineko is mentioned we just gush about it and cry. And shitpost, of course.
There’s also my boyfriend, who has only finished reading EP1. Though he has been very busy with his studies so it’s been impossible for him to continue reading. Granted, I did spoil him most of Umineko, but considering how dense it is, he still gets really immersed into the characters and keeps forgetting who the culprit is, haha.
There’s also this one friend I really REALLY wish could read Umineko, because for one, similarities about the characters and this person, for two, he writes his own characters so well, especially assholes that I just end up caring about and relating to, and I would love love LOVE for him to see the characters in Umineko at their full splendor. He has seen the anime, and surprisingly he liked it and the idea and all, 'cept for the final after credits scene of course. But maaan he has like a million projects and I don’t think he’ll ever have the time to ever read umineko fully. Nor the VN, or the manga. Man he would have loved the manga because the expressions are amazing…
If only umineko had a good anime… then most of my friends could multitask by working and keeping the anime on a second screen or something.
I’ve gotten most of my friends to read Umineko, including @smileypers0n. Now, that said, I also regularly shilled it when I was the president of my school’s anime club, and for every person I got into it, there’s probably a couple dozen who never thought about it again after Club. (Still, I know I introduced it to at least six people who I know are know full-fledged fans now, three of them having cosplayed characters.)
I also got my stepmother to read the manga, which she seemed to enjoy- except she stopped at Episode 3. I think the volumes just got too big for her to consider reading. This isn’t the only time the manga has scared someone away- I have a friend who I got to read all of the Higurashi and the Rose Guns Days manga, but who’s borrowed the first volume of the Umineko manga for almost three months, and hadn’t read a bit of it. (Even though it’s honestly such a quick read.)
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I’ve considered making my stepdad read it after he read the first scene of EP 3 over my shoulder and turned Virgilia saying “…the vase…” into a family meme. I made my sister and an ex-friend read the first volume of the manga, and I’ve made my other friend read all the way up to halfway through EP 5 in the manga. I constantly rave about it to basically everyone I know, but no one ever seems interested, and if they do, they don’t know where or how to read it. What a shame 
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The friends I have aren’t interested in this sort of thing. Hell, most of them aren’t readers at all. For those that are, I try to subtly probe them by asking questions about their tastes, so I can somehow bring this up in a way that will appeal to them. Sadly, I’ve been met with nothing but failure… Doesn’t mean I’ll stop trying though.
I’ve been wearing out my brother for years at this point. What started as a resounding no, has now morphed into “I would rather be doing other stuff, although Umineko doesn’t seem bad.”. Baby steps.
Someday I will get somebody into it, and I will treasure that day for the rest of my life.
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Well, IRL not so much luck.
Online, I’ve managed to get in on quite a few people’s radar at least. The key really seems to be to use the OST and get them to ask where that sweet music is from~.
You have to be patient with people who aren’t that into VNs though. Curiosity has to slowly win out there.
Most ended up liking it well enough, except one who kinda dislikes everything from 07th expansion. (interestingly enough our VN tastes align perfectly aside from that, though I guess I’m less into KEY stuff than they are. Except Little Busters cause that’s just too good.)
I tried to get my ex to read Umineko. I’d talk about it so often that he decided he was interested in it, so I installed it on his PC (I have hardcopies of the Japanese VN). But he never got around to reading it. Never even opened it.
And then there’s my best friend - I’d talked so much about Umineko to her that she wanted me to put it on her PC, so I did, and I still talk about it to her every day. She’s had in on her PC for about 2 months and she hasn’t even made it to the opening theme… I drop hints to her daily about how she should read it, how great it is, but she never gets past “I’ll read it soon.” It’s really discouraging.
Sometimes I think it’ll take witchcraft to get someone to even give Umineko a chance.
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It is clear why you broke up with your ex.
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I’ve tried to get my family and my friends to try it but considering I’m the only one who’s interested in Japanese media I’ve pretty much given up by now, sadly.
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Usually, my strategy is to market it as both “probably the greatest piece of writing to have come out in the last 20 years” and “Harry Potter meets Phoenix Wright meets And Then There Were None” although that second one is a bit inaccurate. I usually tell them that if they aren’t invested by the end of EP 1, they can drop it, but then again, only one person I’ve tried to convince to read it has gotten that far.
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I’m surprised you guys have had some success getting anyone to read it. No one I know really likes Japanese media, and no one I’ve tried to get Umineko has made it very far before stopping, if they’ve tried at all. Even my friends that hear me ramble on and on about it, they sorta just nod their head and give me the kinds of answers you’d get when someone isn’t really invested in what they’re hearing; “Oh?” or, “Aha, sounds cool.” or, “Why?” Sometimes I stop talking because I get so discouraged. Usually explaining the “why” part of Umineko to someone leads to them playing on their phone, nodding absentmindedly, turning up their music, or changing the subject. 
The real problem is, Umineko is basically all I care about, and it’s all I think about. It’s all I ever want to discuss, too, so when I decide it’s not worth talking about to my friends that show such disinterest, they get mad at me when it’s like day 12 with no contact or phone calls or something.
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I pestered my friend a fucking lot and eventually got him the question arcs for his birthday and is currently on the first part of episode 2.
I have another friend who bought the question arcs on condition that I play the Witcher 3 but we both haven’t lived up to each other’s promises just yet. (I got him into danganronpa that he really liked so he now semi-trusts my judgement on good games)
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