Dear Jewish Fairy Godmother:

I dated someone for several months. It started out as “you two should
be friends” from a mutual acquaintance. Then as we got to know one
another better we realized that while there was an intellectual
connection there was no “heat.” We still go to movies and dinner, talk
and text, but it seems pretty clear that it’s not going to turn into an
emotional relationship. The problem: While we were hanging out I met
one of her friends that I am genuinely attracted to. What’s the
etiquette about asking her out? Do I need to say something to the first
date before I do?

Ready to Switch

 
Dear Ready to Switch

No one likes rejection. And a formal, even if mutual, rejection won’t
feel a whole lot better than an informal one. A lot depends on how
close they are, and whether you hope to stay friends with only one or
with both of them. My gut says that unless you navigate this in a good
way, you will lose access to both. The risk-reward ratio is high, but
unless you have a long list of other potential dates, give it a try.

 
I suggest asking the original datee to coffee and asking, Where do you
think we are going with this? Friends or other? Let her reject you first.
Then agree, saying you value the friendship and want to continue to
develop it. Once she says yes to that, chat about other things for a
while. Then ask how she would feel if you asked her friend out. She
may demur, and may want to discuss this idea with the friend. But
leave it in her hands for a week and see if she gets back to you. A yes
is a green light to try. A no is a chance to back down or say you are
disappointed and see if she relents. Without a clear green light you are
unlikely to prevail, and you will always have her voice at the friend’s
ear. But what’ve you got to lose?