Her relationship with Andy has since gotten much stronger and seems to be on the permanent up and up.
Is there ever going to be an appropriate time where Judy and James have distanced themselves enough from each other, and Judy is satisfied enough with her relationship with Andy, that I can ask permission to give it a go with James? I would be content if she answered, "No!," but my friends say Judy has no right to block James from me since she is engaged, etc.
Answer: Are you all fish in an aquarium, and you dictated the letter to your human keeper?
I’ll try answering bottom to top:
Your friends are right, Judy has no right to insist that you and James can’t date.
You can, out of respect for Judy and her relationship, choose to hold off for a while as Judy recovers from her feelings for James (do let James in on this). Then, if you do start dating James, you can also respect the distance between him and Judy as necessary for Judy’s peace of mind, and not throw them together frequently in the same social situations.
Ideally Judy will fall decisively for her fiance — well, ideally she would have before getting engaged to him — but sometimes that just doesn’t happen; people are quite capable of dwelling on someone permanently, and often find they can get on with their lives only if they stay away from that person for good.
There is an appropriate time for you and James to try dating. Judy and Andy’s wedding makes a convenient milestone, but I’m not convinced that day should ever come, or will. If it doesn’t, then I’d say wait till Judy stops dwelling on James — or, alternately, when your interest in James outweighs your friendship with Judy. Whichever comes first.
About the aquarium. If you do all inhabit a smallish world, then it may be that you and James are interested in each other because you’ve exhausted your interests in the other available people. Offices get like this, grad programs do, college buddies do. That means it’s a good idea to question your interest in James before you act on it, just in case. Probably a sensible path with anyone, but it’s especially important when a circle of friends gets a bit incestuous.
E-mail Carolyn Hax at firstname.lastname@example.org, or chat with her online at noon Fridays at www.washingtonpost.com.