First thing I did when I found out Moviechat existed was looked up this question - only occurred to me long after the old imdb boards had vanished to see if anyone else had asked this.
Having read the answers, I now get it. There are so many reasons.
I'll throw a couple of others out there
(1) It's possible that Miles opened the motel room door with every intention of telling Jack, but didn't get chance to because Jack was being insufferable. He literally jumps on him as soon as he steps in the room, when he eventually cottons on that Miles is visibly upset, he starts mocking him, then, when Miles finally snaps at him, and Jack starts to back off, his only thought is to ask if he had "trouble performing". Would have been very interesting, though, if, when Miles says "don't answer it", Jack asked 'why not'. Would Miles have told him then?
(2) Miles' insecurity has already been mentioned on this thread. Given the vibe of their friendship, and the way their lives were going at that point, it's also possible Miles' train of though was something to the extent of 'Jack already thinks I'm a loser, I don't want his opinion of me to get worse by letting him know that I've told Maya.'
(3) Rationally, there was a possibility that he'd get away with it. They're going home the next morning - OK, chances are Maya called Stefanie to tell her as soon as she got home, but it would just need Stefanie to ghost Jack for the rest of that day (far easier to do in 2004), and Jack to not get upset or obsess over not hearing from her enough to turn up at her house or workplace to ask why - and Miles would hope to distract him with, say, another round of golf or a heavy night on the wine until he forgets about it.
Then they would just go home for the rehearsal dinner the next day, so all Jack's focus then would be on his upcoming wedding.
As someone else has pointed out on this thread, Miles avoided confrontation. In this instance, he was hoping Stephanie and Jack would do the same.
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