I have this boring 3 hour history class late at night where you sit and listen to this old lady tell stories. This girl who sits next to me, HB8 is constantly on her phone. We've never spoke. We have a 20 min break and she just texts non stop on her phone. Would it be futile to try to engage conversation?

ALWAYS try. Never assume.

The mental energy you're wasting on wondering is more crippling than any rejection.

Nope! Just offer her something her phone cant...

real life, engaging, positive fun interaction!

U can try the opener "did he call?"

My point being, it's almost a quarter into the school year and we've never engaged. Granted, the class is only once a week, but it's THREE hours long and all we do is sit next to each other bored as fuck. Ever hear "first impressions are everything"? I feel like if I were to say hi or something it would come off as obligated. Why doesn't SHE talk to ME instead.

You care too much. If you're bored, talk to her because it's possibly interesting. That decision should have taken no more than 3 seconds. Not an entire quarter.

Quit wasting time.

I ve pondered about this as well.

I'm not an expert, and I hope some of the more pros in this forum can answer your question.

But I think you just have to create a situation where you can talk to her that is natural. (as opposed to making it obvious that you are interested in talking to her which leaves high chance for immediate rejection) and total future ackwardness.

Maybe you can make muttle something to yoruself about the prof being boring and sees how if she reacts to you (since you are siting beside her and she should be able to hear you even if you are not talking to her).

You stand no chance of winning the lottery if you don't buy a ticket.

I'm gonna come in from a little bit of a different perspective here... Sure, in these kinds of situations it's ALWAYS best to at least TRY!

BUT just keep in mind, even though trying is better than wondering "what if?". You can still get burned by it, so just keep that mind. Rejection hurts either way.
Girls don't straight out reject you. They keep you wondering "hey maybe she'd like me if I do this" "maybe she really is busy? try again!" and this could be a never ending cycle.

(Just advice from a guy who's PMS'ing about some random oneitis at the moment. Take my advice with a grain of salt )