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Feel free to date him again if/when he's ready, but date other people in the meantime. You never know what will happen, either with him or you, while you're waiting.
I also tend to think that if she's not sure after 3 years with you, she'll never be sure. Considering Oliver has been in your situation, it's prolly wise to listen to him.
Nice :-)
My bf was offered a job 200 miles away in a city he's always wanted to live 1 1/2 months after we started dating. I would not have expected him to stay for me so early on. I didn't expect we would continue to date after he left, but we had already grown close enough that he wanted to do long distance. I'm pretty sure if he stayed here and was offered the job a couple years into our relationship, he would not have taken it if I couldn't join him. We are at a different place now 4 years later than we were 2 months in.
I think that you can "treat each other" in ways that don't always involve money, but that's just me. And the point was, all relationships include some type of bartering (one thing in exchange for another). No one gives someone something unless they are going to be getting something in return, because that's just human nature. I think a sugar daddy/sugar baby relationship is just a little more upfront about it.