NOTE: SPOILER FREE. THIS IS INTENDED FOR THOSE WHO HAVE NOT STARTED WATCHING.
One of, if not, my favorite aspect of the at least the first season (just finished it minutes ago) is the blatant cliches, fan service and self-awareness throughout. The whole anime is one huge satire on typical harem shows and it makes fun of those in the best ways. Fan service is almost disgustingly apparent (episode 10 makes you feel the most uncomfortable about it, you'll see), fourth wall breaks occur a few times but are immediately forgotten about by the others (i.e. even if a character displays self-awareness, they are completely ignorant about it when a different character a few episodes later makes a similar joke) to reassure the viewer that this is, in fact, making fun of other harem anime, and the cliches are non-stop in your face. It is for these reasons exactly that "How to Raise a Boring Girlfriend" is wildly entertaining to watch.
I did not go into this expecting what I got, and I really was disappointed some time around episode 4, but trust me, it only gets better from there with some true character development and satisfying interactions starting episode 6 or so. If you don't love it immediately, you'll probably grow to like it more as you continue to watch. If you DO love it immediately, I actually can't guarantee the same for you because that probably means you are hoping for another average harem anime, which is not what you are going to get.
While I do find the original premise to just be "alright", I have to admit that hiccups, quirks and obstacles within the circle of characters thrown into the mix drive the story forward to at least get you hooked on one more episode... again and again and again. The art was quite average for me and didn't really appeal to me as much as some of my top picks, but if you liked other anime like "Sakura-sou no Pet na Kanojo" for the art, then this might just float your boat.
The second biggest part of "How to Raise a Boring Girlfriend" that was why I liked the first season so much was because of how centered on the characters it was. That is as generic as critque can get, but as you continue to watch, you can only see the improvements of almost everyone in the spotlight. Part of why the first few episodes disappointed me was because I disliked several of the characters; their manerisms, personalities and even their designs. But as I got closer to the end of the season, I began to realize that every character was created as a mold of what the creators wanted them to become by the end. You start to see fragments of how each characters' arcs will unfold and what strides they will go to improve themselves and their relationships with each other, and that is PIVOTAL to point out and understand. Without this format going for it, this anime really doesn't have much else besides some clever jokes and humurous dialogue here and there.
TL;DR - You should watch "How to Raise a Boring Girlfriend" because you'll become so much more attached to every character as you watch that you won't be able to find a good place to stop, however don't let the over-the-top cliches and blatant satire on the harem genre ruin a thoughtfully crafted anime.
