@Diest TKO,
Diest TKO wrote:Would you date your sister's best friend?
Well, my sisters' best friends are not available, and they live an ocean plus half a continent away from me. But technicalities like these aside -- sure, why not? My sisters' best friends are delightful ladies, just as my sisters themselves.
Diest TKO wrote:If so, when would you tell your sister? Before, when you are interested or after when there is something to say?
As soon as I'm interested. Sure, I would be a bit shy about involving the sister at this point. But it's worth it: My sister is guaranteed to have insider information I can use to fine-tune my approach. You know -- choosing the best timing, finding the best angle to hit on her from, and all that. Of course, much of that depends on on my relationship with my sisters, which is close and mutually trusting. So if you don't mind my asking, how would you describe the trust, the comfort level, the overall relation between you and your sister?
Diest TKO wrote:Would you date someone who is in a relationship?
In principle, yes. I would add a lot of "if"s and "but"s if there are children involved. But if the only thing you worry about is the relationship between your potential date and her current lover, my answer is a plain "yes". If she's happy where she is now, she'll just say "no" to you. Conversely, if she ends up preferring you over him, that in itself proves that her present relationship didn't deserve to survive. Either way, let it be her choice, not yours. You are not the warden of her other relationship.
Diest TKO wrote:If so, how long would you give them to break up with the other person before forcing the issue?
That's a very good question. Why don't you discuss it with your sister?
Full disclosure: The author of this post has been single for 18 years. Don't take any relationship advice from him without a spoonful of salt.