Good question. They shouldn't sound the same! It might happen if someone's speaking very quickly. You *should* usually at least hear the "t" in "whatever", even if only softly/quickly. Some speakers do drop the "t" completely -- this may be confusing you. American English speakers may produce the "r" in "wherever" more strongly. Go here and click the icon to hear the words pronounced: http://www.thefreedictionary.com/whatever http://www.thefreedictionary.com/wherever http://www.merriam-webster.com/dictionary/whatever http://www.merriam-webster.com/dictionary/wherever

If you're not sure, just ask the other person to speak properly. No need to beat your brains about it.

"whatever" means no matter what, " wherever" means anywhere, in any direction. Since the meaning and spelling of these words is different they can't be pronounced in the same way. "what" and "where" are different words.

Actually Jmat, you got my point. I was tinking that the flap T was pronounced exactly like the "R" sound. But now I get it. Thanks!

When people speak quickly, Ts often become Ds. A lot of people regard this as poor English, but it's still very common. I've heard that English Ds sound a lot like Spanish Rs. Maybe you're hearing people say 'whaDever' and confusing the D for an R.