Hopelessly Devoted. (It's long but I could really use some advice.)

[Confuzzled4]

Honestly, I don't think you should count on a romantic relationship with Tom. If he really wanted to resume that kind of relationship, he would have done so already. Take a break outright from Tom for a bit and focus on dating. After a few weeks, you can see if you can resume your friendship with Tom. I think you can still maintain a friendship with Tom, but take that break first. I'm being blunt only because I had my heart broken in the past, I don't want that for you.