I'd love to try karaoke in Shinjuku, but...

Ever since I booked my flights for my solo trip to Japan this coming March, I've been reading travel guides and talking with people I've met briefly who have gone before, and I feel like I've heard three or four times, "You HAVE to try karaoke!!"

I would never do 'western' karaoke, where you sing on a stage in front of a room full of strangers, but the Japanese version, where you get a private booth with a few friends and a few drinks sounds really fun.

What I'm wondering, though, is whether it would actually be any fun to get a booth by myself. I know it's possible, but that just sounds depressing. I really wish there were a way to meet a few locals my age (mid-twenties) and try it with them. Perhaps that's just wishful thinking, though? Any experienced karaoke buffs out there who can recommend some options for me to have a fun karaoke experience?

Where are you staying? If you are staying at a youth hostel you may meet up with others (including Japanese) who are also interested.

Enjoy your trip!

A lot of people go to karaoke by themselves.
It's often though for practice so they can impress when they go with friends.

I would put karaoke up there as one of the easiest ways to connect with people, even people you've just met.

Of course you have to be careful but if you happen to meet some girls and you start up a conversation, it would not be strange or out of line to explain that you really want to experience karaoke and ask if they have 1 hour to take with you.

I'd put it on the same level as "hey, you want to go get a cup of coffee"

well I did it by myself and its still fun. Try an afternoon when rates are cheap. I went to Karaokeken in Takadonobaba. You pay per 30 min unless you go for a special deal. In the afternoon I paid something like 89yen + drink (non alcoholic around 300 yen). So fun. Otherwise like someone mentioned try people from hostels or try on here or get a tour guide on the free tour guide site(you pay for the activity) or meet people on couch surf site for activities.

You could try singing in a Karaoke booth on your own, but I don't think it would be very fun. If you can't find people to go to Karaoke with, you may want to try and find a small bar that has Karaoke. I know you said you don't want to sing in front of lots of people, but there are lots of places that seat only 10-15 people. I wouldn't like to sing on a stage in a western Karaoke place, but I've never felt uncomfortable singing in one of these small bars.