Most movie fanatics seem to operate on the thought process that what they like is the best, and in order to further educate their family and friends, they must force their own favorites on everyone else in an effort to expand their horizons. It's a natural response, but ultimately a fruitless one. Granted, you may turn some heads and generate a new fanbase for the art you admire, but for every recruit there are equally as many detractors; the punchline being the latter category won't be able to fully trust your recommendation ever again. There is a time and place for passion and forcefulness, and getting people to watch the things you like because you like them is most definitely not that time and/or place. At least, not if you really care about or respect the artform -- not to mention your friends.
I learned how wrong and useless this was when I enthusiastically had a cousin of mine watch The Godfather about 7 years back, knowing that this would be an eye-opening learning experience for someone whose idea of classic film often involved any combination of Arnold, Stallone, Chuck Norris, JCVD, or Jackie Chan. Needless to say, he was practically asleep by the first hour -- we would watch Superbad later on, during which there was a scene that caused him to erupt into uncontrollable laughter for somewhere close to 7 minutes. As it turned out, it was much more of a learning experience for me than for him. My presumption resulted in 3 wasted, aggravating hours watching one of the greatest movies of the 1970s with someone who could never appreciate or enjoy a piece of art that I have long admired. This forced me to rethink my approach.
There are no objective truths when it comes to the appreciation of art: music, film, television, painting, sculpture, or anything else. Nothing that truly speaks to you on an emotional level is guaranteed to appeal to everyone else, and that's the way it should be. If everyone liked the same things, there would be no need for artists of different varieties. In fact, there would be no need for people of different varieties. We would all become a gigantic mushy pile of boring, gelatinous clones without any distinct personalities or interests. Now wouldn't that be fun? So, what I'm saying is next time a friend tells you how hilarious the new Tyler Perry or Adam Sandler movie is and that Suicide Squad was actually good, don't judge them for it. Just appreciate that they aren't the same as you, refine your recommendation mechanic, and move on.
So how do we go about adjusting this mechanic? It's simple, really, and it all comes down to knowing your audience. If you want to talk movies (I'm using movies as the example because that sums up close to 35% of everything that I care about, but this really applies to anything) with someone, the first natural questions you come to wind up being "what are your favorite movies?", "who are your favorite actors?" and "what kind of movies do you generally watch?" or something of that variety. Now here's the next step, and it's definitely the most selfless and useful of them all. You ready? Pay attention. It sounds simple, but if you actually give a flying crap about movies and speaking to people about them, you will listen to what they have to say, why they like what they like, and maybe you'll even learn something about it. Conversation is key, and listening is half of that process, so actually try not to zone out.
Now, assuming this person shares any of your interests within said artform, and assuming you've actually watched/seen/experienced enough to make any recommendations or converse with them about their field of interest, this is the part where you can shine. Let's say this person is a huge fan of Will Ferrell and has seen virtually all of his movies. This isn't exactly an uncommon scenario, so you can throw out a few of his more obscure or fringe movies that this person may not be aware of: Stranger Than Fiction, Everything Must Go...you get the idea. While they may never have seen these two movies, they're both distinct enough departures from his regular formula to make for interesting recommendations, or (assuming they've already seen these) could at least serve as building blocks to help flesh out their tastes. You don't instantly throw in a Tarkovsky movie and hope that it sticks, you need to ease people into the difficult stuff -- if even at all.
Or perhaps you can bring up a similar actor, like Steve Carell. His filmography is filled with me difficult material that can challenge audiences into thinking a little harder about what they're ingesting. If they like Carell, plug this person into The Big Short and make sure they realize what they're getting into first. This isn't saying that people are so dumb you need to condescend and baby-talk them through a more difficult movie, but it never hurts to establish a firm footing before trying to leap up that rocky incline. No one has ever gone from Chuck Norris to Tarkovsky, and while not everyone even can appreciate and enjoy these things, if you really want more people to see eye-to-eye with you, you first need to see eye-to-eye with them. You don't go from Delta Force straight into Andrei Rublev. Instead, go from Delta Force, to RoboCop, to Total Recall, to Blade Runner, etc. and hope for the best.
In the end, the odds are they'll never be into Tarkovsky, and it's your job to be okay with that and still try to find new fun and interesting things that they actually will enjoy. This is what you signed up for the moment you decided to be the movie guy, so take on this role in a useful way and try to expand horizons gradually and recommend appropriately. My mother is never going to watch old foreign movies or weird horror, but that doesn't mean I can't find new things for her to watch all the time. Part of the benefit of having seen thousands of movies is for that particular reason. Share your knowledge, don't be condescending about it, respect your people, and respect the artform.
Nobody takes recommendations seriously when they're from someone who has proven time and time again to not actually care what you think. I've known plenty of people who repeatedly recommended movies to me that were total crap purely because they watched it, liked it, and that was good enough for them to waste my time with it. If they had bothered to learn what I enjoy at all before recommending something, they would have probably not told me how badly I needed to watch [insert random garbage horror movie filled with idiotic jump-scares and generic plot and characters], because I've essentially seen and disliked this same movie 20 times already. This leads to an entirely different point that needs addressed: never highly recommend a movie just because you want to talk to someone about it.
"But why not? Conversation is important, you said so yourself!" This is true, but if you ever want someone to really listen to your recommendations again, these kind of experiments need to be approached delicately and very deliberately. Never say "you need to see this movie, I really liked it" about something that you just want to gauge reactions from. You need to inroduce this kind of thing with "now I don't know if you'll really like this one very much and it's pretty weird, but..." and, as ominous and foreboding as that sounds, you'll often be greeted with a much more positive reaction from people because they won't go in expecting to like it. It's all in the way you frame it, and your introduction alone has the power to compel someone to love or hate something. We're impressionable creatures, so don't abuse this gift, especially not if you've already earned their confidence in your power of recommendation.
In the end, recommending movies is all about spreading a love for film. If you don't have anything to recommend, don't waste anyone's time and wait until you do. There are so many wrong ways to do it and you'll often only wind up disappointed if you go about it in the wrong way. It may sound ridiculous to some people, but it matters to people like me. Hopefully this is helpful to at least someone...I know I'd recommend this post.