That's what I was thinking when I saw Wesley at the end of Life of the Party.
Again, Fred thinks of him as nothing but a friend. Again, he's feeling isolated and alone.
But he doesn't know that it's 'again'.
This is part of why the alleged mind-wipe/world-change is a bad idea (other half rests on whether or not you believe that Connor needs to redeem himself not to go to hell when he dies - a chance that his father took from him, not knowing the extent of his son's crimes) on Angel's part (personally, I do agree with Angel's motive. It was stupid of him, but... it was his kid. Probably the only one he'll ever have. I get wanting him to be happy, no matter what.). Angel has, to all appearances, condemned Wesley to walk the same road that led to Wes' first fall in S3, unless something happens differently this time around.
Now, everyone else has different circumstances. Fred met a geek boy that she likes, meaning that she and Gunn won't walk down that road of disappointment. Gunn has augmented himself, made himself more than the muscle, meaning that he'll deal with his feelings in different ways. Lorne has found something that is actually his type of thing.
And Angel, of course, remembers. He gets to make all new mistakes.
But Wesley is the only one without a place, without a true purpose. He came to Wolfram and Hart to save Lilah. That motive no longer exists, if Connor and Wesley's Fall To The Sexier Side don't.
They gave us little teases of Lorne before this episode, leading up to what would happen here. They're giving us little teases about Wesley and the memories as well, and I do believe that they're leading somewhere. He questions the decision to move to W&H in Conviction, can only bring up a pen as a perk in Unleashed, and in this episode, we saw a room where they store pieces of people's minds/personalities/feelings.