Tricky Trio

My friend (we can call her “Jane”) and I have a really good “guy-friend” (we can call him “Jack”) that we (*gasp*) “hang out” with quite frequently. It is usually just the three of us, and it is always fun. But that’s just it…fun…not much else. “Jane” says she really likes him and would like to get a relationship going, but he doesn’t seem to like her like that. To make the situation even more awkward, “Jack” and I have gone on several actual dates (albeit casual ones) before “Jane” started “hanging out” with us.

There are many people outside of our ‘Tricky Trio’, that think that “Jack” and I should date. But that is easier said than done. I am not entirely sure if “Jack” likes me more than just a friend, and I am not entirely sure if I like him more than a friend. But the situation is such that I feel pretty uncomfortable “hanging out” as we do, because we don’t really meet new people. It almost feels as though we have no other possibilities, I suppose.

I have told “Jane” that I would ‘make myself scarce’ if she wanted to start a relationship with “Jack,” but she says that she likes spending time with everyone together. I have tried to get other people into this “clique” in hopes to lighten the mood a little, but it just doesn’t seem to work, and I don’t know what else to do before “Jack” and “Jane” and I end up tumbling down a hill of ruined relationships.


Dear Jill,

Wow! You have a lot of intrigue going on here. You seem to be assuming a lot of things without a lot of real information and you are either putting yourself in the middle or letting yourself be put in the middle of this situation. First of all you must ask yourself two questions: What do you want? And, are you sure you don’t really like “Jack”?

When you are sure where you stand, then you will need to be honest and tell both of them TOGETHER how you are feeling. You need to let them know you are going to pull yourself out of the middle and you are going to include others in the clique. The goal here is to have everyone on the same page in terms of information and then let them figure out their own stuff! It’s easy to fall into the same routine with the same people so you could also limit yourself to hanging out with the two of them no more then once a week and proactively plan activities with other people that do not include “Jack” and “Jane”.

You can only speak for yourself but you need to “let them know and let it go.” You should be having fun not stressing out!!

Good Luck Jill!
— Karen