How long should I give a guy to let me know what he thinks of me (or at least hint)?

My dream boy knows I like him... we have become better and better friends over the past few months. He has asked me to study with him, told me things I do are sweet, been caught staring at me, told me he wants to take a class with me next semester, and is generally an amazing guy. Most recently, we were studying for a final together and getting ready to leave and he was kinda shy and was worrying about if he was bothering me by staying so long. He seemed happily surprised when I assured him that it was fun for me! Now, we are on winter break and don't live too far from each other. I told him in a Christmas card that I'd miss him and hoped we would see each other over break some time. The situation is kind of unique because there is something to deal with that makes it hard for us to spend time alone together. I have a situation where because of a medical issue (nothing too severe and something that anyone can take care of once they know how to handle it) causes me to almost always have someone with me. I know it's hard to deal with but we are still amazing friends and I hope there can be something more. I know that anyone, minus the medical issue, would need time to take action and find the right time to ask me out, but (if you think he likes me) when should I consider it a lost cause and settle for friends? I am patient in general but when do I worry?


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