Yeah, that makes sense. Living vicariously through Starfleet briefings and they actually get the chance to put all that "practice" to good use.
The wrinkle is that "official" documents aren't always accurate about things like personality/what actually happened versus the sanitized "for publication" version. So their memories of what "happened" may be totally different, or possibly include missions that never happened.
Further, there's the crew this person supposedly "knows". So the guy this character doesn't like may actually be a decent fellow, the one they're best friends-ish with doesn't get along with them, and the person they like is in a relationship already/isn't interested in them.
Talk about emotional whiplash. It's also kind of a metaphor for fans who'd like to be in on the action themselves. Could you actually handle it? I know that sounds like a Mary Sue-ish fanfic, but if written right...
The other idea I thought of was this person who flunked Starfleet Academy, but his parents shut him in a holodeck and convinced him he was still in it and had gone on to be posted on a ship. Then that same ship visits; the parents try to keep it a secret from the ship, but the crew finds out and so does their kid. Shattered and angry, they lose it or at least are very hurt by the truth.