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Do you hold it against your friends if they don't read your book?
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I've also had people who've bought my book right after I told them about it but down the road when I asked them if they ever got around to reading it they say "oh not yet" or "yeah I read the first few pages but that was a while ago".

Yeah, I have hundreds of facebook friends, and some of them are very dear to me... I think out of all those hundreds, maybe only three have ever actually bought anything I've written, and that was after quite a bit of spamming of their facebook and/or email mailboxes. And one of them was my mother.
In my opinion, I think you need to separate the publishing / P.R. side of you from the social side of you. Some of your friends might just not like to read. Others might just have their plates full. Importantly, I don't think it's wise to take it personally if they fail to take the time to buy & read your books. I know several amazing artists and I've never coughed up the dough to buy their paintings or photographs. They still love me, I still love them.
Book sales are not love; love is love. The two things should be separate, in my opinion :-) If some of your friends support your publishing goals, great. If others don't, it doesn't matter; plenty of strangers will. No need to judge them by separating them into "good" & "bad" categories. After all, do you only consider them friends if they are willing, or able, to take the time to buy your work? Probably not. Thus, such a division isn't really fruitful, and might just end up putting a wedge in your relationships with them :-)

It still gets to me a bit. But it's also never going to change. I don't know why it has to be that way, but it usually is. But I also don't bend over backwards to support their various endeavors either. If it interests me fine, but I don't tend to put extra effort out when I don't receive extra effort as needed.
Some of my friends do read my work, here and there.

Heck, I think even my parents haven't bothered to read my book, haha.



I think if you want proper feedback (not just empty platitudes), then you need to specifically say so. Like: "If you don't like it, I really want to know, because that's the kind of feedback I need in order to improve my writing. I won't be offended, and I won't stop being friends - in fact, I'll be really grateful."
As to how many times it's acceptable to ask someone to read your book/whether they've read it yet, from personal experience, probably once - if that. If I have the book, and I know you, every time I see you, I'll remember the book. Any more than once is nagging, which is associated with mothers and room-tidying. Grown-ups shouldn't be subjected to it.
If someone hasn't read your book (yet), it probably isn't their style. Or they have read it, but they didn't like it and don't know how to tell you. See above regarding making sure people know that you aren't going to go off in a snit, or throw a tantrum, if they tell you they didn't like it.
So, if you want proper feedback, let people know. It takes courage to tell someone that you don't like their book - just as much courage as it takes to receive negative comments with grace.
It's much easier all round if you - the author - take the initiative and let your poor reader friend know that if they say "It wasn't for me" you won't throw your drink in their face and challenge them to a duel to the death. Or unfriend them on Facebook, even. :)


Andrew, I also get annoyed at the people who say, "I'll totally buy one!" and never do. (Note, I've had many supportive friends buy my book; I'm not sure how many have read it.)
AJ, I always carry copies with me (or in the car). I say, "Great, $15."
Then the excuses are, "I don't have cash on me."
I answer, "I have a credit card reader." (Squares are $10, so worth it.)
Then they say things like, "Uh, I don't have a credit card on me." Or it becomes, "I don't have time to read right now" or "I can't afford it right now."
Really? Okay. If you say so. (My roommate and I have this conversation every few months; she reads fantasy, too.)
Not the new moms, most likely. Many of us prefer to be left alone in the first few weeks after having a new baby. Too many germs come in the house along with the visitors, and new moms are deep in the bonding process and don't want people coming to prod their newborns. Not everyone is like this, of course, but I definitely am. ;)
As for your original topic, the part I have a hard time with is when I don't hear back from my friends or family about their impressions of my book. Someone else said this already, but I'll say it again. Until I hear from a friend or family member that they liked the book, I worry about all kinds of things: did I waste their time/money, did they hate it but are afraid to hurt my feelings? I feel very strongly that self-published authors should be the ones who bear the burden of proving their work is worth investing in. Friends and family should never be pressured to support an author, no matter how good that author may be. I would much rather have them buy it sincerely out of their own interest, and then tell me to my face that they didn't like it, and feel comfortable doing so, than do anything to make them think that they can't be honest with me about their interest (or disinterest) in my work.
I do understand that instinct to divide people into lists of who did read it and who didn't. How many of us have friends who we know would totally love what we write if only they would give it a chance, but those people just don't seem to be interested. Several people made comments about friends who say they will buy the book and then don't, or people who don't reciprocate support that you give them on their "business" ventures, and those situations only add to the frustration.
But then come the moments when a total stranger randomly stumbles on your work and leaves an incredible, totally unsolicited review, or when a friend you haven't talked to in ages comes out of the woodwork and starts telling all of their other friends about your work. Those are the moments we write for, and they help us pull our perspective back into alignment. People are free to make their own choices, and while those choices sometimes give us pain, there are lots of other people making choices that bring us great happiness. It's our lot as self-published authors, and how lucky are we that it is even possible these days. It used to be much, much harder.