Dear Kitty,

There are many uncertainties in your current situation, but what’s for sure is that neither Sid or Jake want to date till they enter their respective colleges. The big difference being that Sid doesn’t want to date at all until he finishes college, whereas Jake wants to, once he gets in. What is also sure is that Sid’s parents are strict and it appears he’s afraid of them more than he’s attracted to you, because he visited you only twice, even when you were in the same city.

If I understood well, you broke up with Sid mostly because of long-distance, i.e.  mostly because of you because he’d be fine with long distance, since he wants to focus on his studies anyway, and dating isn’t his priority. Once, when you felt bad and needed his support, he even told you “we can’t do anything and we aren’t gonna die if we don’t meet”. This tells me that he isn’t that disturbed that the two of you aren’t together at the moment. He’s assuring you that you’ll be together after college, and in the meanwhile he seems pretty cool about you not being together. He’s even telling you about a girl he likes.

My impression is that you’re actually afraid that you’d lose both Sid and Jake because if you tell Sid about Jake, he’ll get angry and jealous (you said he was possessive in the past), and you might lose him forever. But I believe you might lose him anyway, because he doesn’t seem as attached to you as you are to him. Four years of college is a very long time, and in that time, both you and he might have multiple relationships. You’re young and so many things can change. So the fact that he’s telling you that you’ll be together later might be just something he’s telling you to make you feel better – unless he really has a strong intuition that the two of you are meant to be together. But if so, he wouldn’t be having crushes on other girls, I suppose.

What I am trying to say is that even though you believe Sid couldn’t live without you (“the thing is I really don’t want to break his heart by telling him about Jake”), I don’t think he would be that heart-broken as you believe he would. My impression is that you’re more invested in your relationship/friendship than he is.

So my suggestion is to take a look at what you want, and not worry so much about Sid, because Sid will most likely be fine. But will you be fine without him, that’s a question. Try to answer that question for yourself, honestly.