Diary of a Network Geek

No, really, I have this friend who wants to know what people think.

Specifically, he wants to know what people think about a particular question.  See, it’s like this…
So, about a year ago, this friend of mine started dating someone he met via eHarmony.com. Well, things started slow with this woman, but he’s a very rational guy and allowed logic to guide him.  She had many appealing qualities, so, even though he didn’t have an immediate romantic attraction to her, he stayed the course and did his best to make a connection with her.  Sadly, it didn’t work out.  He could never quite get any chemistry going and, in the end, she obviously never felt that either because she pretty much broke it off.

Well, it turns out that was okay with my friend.  Why?  Well, as wrote previously, he never felt any real chemistry with her.  But, more than that, there was a complication.
The complication was a sister.  A single sister, as in not-married.  It seems he had an immediate reaction to this sister when he first met her.  In fact, one could say that all the chemistry he was hoping for with the original woman was, instead, centered on her sister.
Her sister had been seeing someone, sort of.  He was also from eHarmony, but he was from another state and, well, apparently there wasn’t enough chemistry.  So, even though she was kind of involved when my friend met her, she’s single now.

Now, here’s the dilemma…
After having dated the one woman for a year, can he now ask her sister out?  If so, under what conditions?
There are a few details that may be important, too.  First, these two sisters are Phillippina and pretty conservative Catholics.  Secondly, my friend is a staunch Christian and, therefore, is waiting until he’s married for sex, so that complication is not an issue.  Thirdly, my friend is very much NOT Phillippino and a Protestant.  Also, he’s waiting a respectful time before he’ll even contemplate asking the sister out, but, that time is drawing near.  Though, that raises another question, though.  What is a respectful enough time to wait before asking the sister out?  Oh, and should he ask the first woman’s permission first?

Right, so vote on the poll in the right side-bar, okay?  And leave any thoughts and insight in the comments.
(And, yes, I am talking about an actual friend, not myself in disguise!)

Advice from your Uncle Jim:
"You may give out, but never give up."
   --Mary Crowley