Should I even bring it up?
479425
I wouldn't bring it up.  It will cause a wedge between you and your male friend because it would be breaking his confidence to email her.  Let it go and keep him as a friend.  She needs to trust him more if she wants to keep him.
597848
looking at your long, long story, it really seems to bother you. so why don't you just ask and find out? if he accepts, great! if not, then at least you got piece of mind. in summary, you can only win if you ask. therefore: go for it!!
1177524
Be careful with that.  You could talk about it with her first and I would definitely suggest that.  Some women are into it and some just never ever will be.  Talk it over.
118425
Ah, dumb move on your part, I'd say.\n\nHe's going to find out. \n\nYou can be honest and tell him, or somebody else will.\n\nYou have a real problem here.\n\nlol lol lol  Give tompj64us best answer, PLEASE!!
1100093
Tell her if you don't want to worry about this issue popping up later. Things might get nasty.
764657
You can ask but you might get sued over it.\n\nCoach
24234
Most guys would say, "oh, that's lame... you should shoot yourself for even asking it." but the smart guys >like myself< know that's something women would find cute. It might not be something to say on a first glimpse, but to a friend you are trying to up your relationship with, sure!  good line for that
571393
TELL THEM!!!\nit screws up your whole relationship if you don't.
1150650
It's best for you to be a little honest and ask for what you want...you might be ok with it now...but if it keeps up you might get a bit resentful about it. And if you don't tell her, she might not even know! She might think that you are fine the way things are cause you're not saying anything...most important thing I've learned about relationships...gotta ask for what you want...your partner is not a mind reader!
539739
Just ask him about it, usually if there is nothing to hide he'll just answer you... but he may not want to answer because he thinks your accusing him of something... if that's the case just drop it until you have proof something is happening... Its probably nothing to worry about :)
1004759
from a guys perspective just play it cool but maybe bring it up and ask how was it
784129
You should do it because if not she might be abused and even killed. Then would you hate yourself? She might be very thankful that you told her about it before it gets to serious. Tell her soon
185494
I would ignore it.  There are more important things to worry about...for instance the people you actually care about.\n\nLife is too short to be petty.
848714
Ask him again, say something like "hey so what do you think, would you like to go out".  It could not hurt.  Curious as to why he never did, or does not bring it up, but you should DEF. ask him again, call him out on it.
645402
I can see some of the time - but most of the time you should be up front with her. (What has she told you when you've asked her about it?? - I hope you have discussed it)
993793
I don't know if you can do this subtly but sometimes for the good of the relationship you have to voice your concerns. Be respectful of course and gentle. Not aggressive, but make them know you only mention it because you value the relationship and you want it to grow. I think you may be surprised, hopefully pleasantly.
516866
if it were me i would just make conversation and bring it up...i think guys like it more if its just straight forward...so just tell him.....say it like..this is gonna sound stupid but i really like u'....he will say somthing back...