Now normally I would assume it always makes more sense to ask Y for quicker results, since it seems generally easier for a company to give you results sooner than it is for a company to extend a deadline they already set.
HOWEVER, there are a few specific circumstances in my case and I want to know if they change the situation.
Company X, which hasn't gotten back yet, is my #1 choice and I desperately want to work there.
I have informed Company X about my other offer deadline twice now. Once when I scheduled my final interview with them, and a second time in my "thank you" email which I sent after the interview. In that email I also asked when I'd hear back, but never got a response.
I have heard absolutely nothing back from Company X since my interview four days ago. I know it's only been a few days (like 2 working days), but I let them know about this deadline twice already.
Company Y's deadline is in two days.
Whatever I do, I think it's best to do it tomorrow, since I'd rather not ask for a deadline extension from Y on the day before it's due, or demand that X tell me their decision with one day's notice.
Any suggestions on how to deal with this situation? I could do nothing and wait it out, hoping that Company X will honor the deadline I gave them twice (though they never indicated they would abide by it). But since I want Company X very much I don't know if that's a good idea.