Living near NYC for so many years and being a consumer of creative arts, I should've seen many more Broadway shows by now. However, I was busy attending other kinds of music performances and forgot my love for theatrical productions. It's been re-ignited thanks to a couple of tips I've collected over the last few months, so let me share some with you!
Bi-annually, there are time frames in which one can purchase two Broadway tickets for the price of one. Be on the lookout for those weeks so that you can get two tickets to share that magical experience with someone.
A friend of mine has won so many Broadway Direct Lotteries (which provides the winner with a discounted ticket) and was able to see up to 5 musicals now, thanks to that lottery. Granted, she also works in Manhattan, so it makes attending performances a more convenient matter.
You can wait in person on line before certain shows start to get discounted tickets up to $35 value, though these tickets are limited in quantity. Also, instead of playing the lottery for shows like Hamilton, there are standing room and understudy tickets, which require more determination to get.
TKTS has good booths around the city that give discounted prices that you can't find online, all the way up to half-price tickets to Broadway shows.
Headout.com gives you a choice of which general section you want to sit in, but they will purchase the tickets for you in person. I've reserved tickets for three shows now. I can't say enough about the discounted price that I've gotten from that. (It's so much better than Ticketmaster.com.) It's been easy to use each time! I enjoyed a great rear mezzanine seat to see Wicked and awesome price on rear mezzanine seats for The Phantom of the Opera. I have yet to see how my Anastasia reservation turns out!
Broadway Roulette has good reviews from people that use them, though a spin can cost you around $60. I've "spun" the roulette once and was sent to see Chicago. If you're a bit of a spontaneous spirit, and you keep an open mind, you might be surprised with the show you'll get. You are able to eliminate shows from your spin, and it keeps of track of shows you've watched before.
One more pointer...
If you're thinking of attending non-Broadway musical experiences, other great value ticket sites to find discounted tickets include Vivid Seats and Seat Geek. I've been able to find Ed Sheeran tickets as low as $65, and I'm regretting that I haven't purchased them in time. Luckily I've been able to nab ~$50 tickets to see Lady Gaga a few days before her last summer concert by being able to wait patiently until the prices dropped.