I’d like advice on how to handle some things I’ve noticed about my boyfriend of almost three months. A few times since dating, he has sent back food at a restaurant — not because the order was wrong, but because the dishes did not live up to his expectations. I think I have sent dishes back maybe like two times my entire life, and it’s been because the orders were wrong.
Then on one occasion, we ordered two glasses of wine, and the waitress indicated she would bring us a carafe. When he received his ticket at the end of the meal, the carafe was either $2 or $4 more than it would have been if we would have just received the two glasses of wine. He proceeded to write a note on the ticket. I was so embarrassed. To make matters worse, the next morning, we went out to breakfast and I paid. At the bottom of the receipt it had gratuity recommendations and $7 was 15%, so I tipped $7. He then asked me why I only tipped $7. The night after he didn’t tip a waitress and wrote a note on a receipt!
I can’t decide if I should say something to him about this. I Feel like this could be a character flaw, in that he is extremely picky.
LemonVibe 
Oh that’s a huge red flag. He’s going to treat YOU like this. Run.
First off, I actually agree with your boyfriend that 15% these days is on the low end when it comes to tipping. Assuming you’re in the United States, the whole wage system for service industry workers has gotten pretty messed up over the past few decades. Nowadays, my general rule of thumb is 18% at the minimum for standard-level service (i.e., as long as they haven’t screwed up royally), and then 20% – 22% if you feel like the server did really well.
Also, that carafe of wine is likely to be bigger than two combined glasses, so the extra charge is perfectly valid.
Regardless, the issue I’m seeing here is that your boyfriend seems, for lack of a better term, a bit entitled when it comes to dealing with servers. Like, he believes servers need to live up to a certain bar that he’s set — a bar that isn’t particularly reasonable.
Don’t get me wrong, though. It absolutely is okay to complain if you believe you were overcharged. You just don’t do so by taking it out on the server. You ask them about it politely, not via some passive-aggressive note and no tip.
It’s also okay to send a dish back if it was made objectively poorly or outright incorrectly. But if the only reason is because you don’t like it — yeah, that’s not cool. You shouldn’t make the restaurant pay because you made a poor dish choice. It is a fine line, but his having done this “a few times” in the three months you’ve been dating definitely seems excessive.
Does your boyfriend have any friends in the service industry? Given your description of how he behaves, I’m guessing he’s never worked in any sort of service or customer service capacity. And because of that, he believes he’s entitled to a certain level of service that borders on pandering to him and isn’t reasonable.
So I think the solution here is to help him humanize the service industry a bit. On way to do that is to look up and share with him articles and blog posts about what it’s like to be a server or work at a restaurant. Not just tipping guides, though, but first-person accounts. These types of posts will help him get an understanding of what it’s like to be a server, and hopefully then, he’ll learn to be a bit less entitled and a bit more respectful to the people serving him.