Yeah, I think he really wanted the ease that he'd once had with Stella. He'd fallen for her so young (and now I wonder how much of that was in response to her belief in his heroism) and had felt so unworthy (con-job).

With Fraser, he gets all dependent, yeah, but he feels worthy. He gets the love thing -- he doesn't fight with Fraser or chase Fraser. He just waits to see what Fraser decides. We know how deep in Ray is from his speech earlier in the episode, but he still does the "I'll understand if you don't pick me," which he could never do with Stella, because his love for Stella was ultimately immature. It wasn't about her, it was about him. Without Fraser, he knows that he'll feel lost and alone again, but he wants Fraser to be happy, despite the cost to himself.