Dating your buddy's sister...

Assuming no earth shattering fallout with her that would cause a riff with your buddy, why not?

She's butt ugly?

because what if you have an earth shattering breakup with her that threatens your friendship with your buddy?

What if you have it out with your buddy, thraetening your supply of... well, you know.

I'm not sure of the relationships here.

"Your man's sister" -- does that mean you're gay, and in a relationship, and so you have 'your man'?  Or does that mean you're female, and in a relationship with 'your man'?

In any event, somebody's sister would then be dating your sister.  Now we work through that your sister is gay, I suppose?

I don't know, it must be the end of the day, I'm just not getting it.

Allan: Go to bed, old man.

Oh, okay, so you (male) want to date your buddy's sister.  Got it.

Hmm.  Possible loss of friendship with buddy should relationship not work out.  Possible discussions at home between buddy and his sister might make you look bad.  Buddy might have a problem knowing his sister is being sexual with somebody he knows -- assuming it goes that way.

If everybody is cool with it, why not?

LOL

Well, I've known her a long time. It would take something pretty out of character for either of us to be that awful.

She's actually quite attractive, just always overlooked her in the past for the obvious reason.

Things have been going good, so my nature is to second guess it... Just wondering what I might have missed.

I wouldn't do it if you lived in a trailor park. It's not done to steal your best mate's girlfriend.

That would've been funnier if you weren't smoking crack when you typed it.

If your buddy is female, you should be dating them both.

Can we get Stephen a green checkie?  It wouldn't have any currency here, but maybe as a reminder of days gone by...

You got a pict of her?