I don't get to sing karaoke often — less than once a month, for sure. But I still have a karaoke playlist on my phone that I frequently add new songs to. Karaoke is just plain fun — even if it's not a regular pastime.
If going into a dark room with a group of other people to sing classic hits makes you feel terrified, don't be! Karaoke bars are a super-relaxed way to have fun with your friends in a closed setting — and it's way less intimidating than getting up to sing in front of a crowded bar.
The key to having a fun karaoke night is choosing songs that the majority of people will recognize. Karaoke night isn't the time to show off your love for cool indie bands. (And chances are, the lesser-known songs might not be available to sing, anyway.) Singing cheesy songs is often more fun, too, because there's no pressure to perform them well.