I've not dated anyone with that sort of persona or personality attribute, however, I did know a few of them in my youth. They used to brag about anything and everything they had in their house and what they did during vacation and why he doesn't have any pictures because they were 'too busy having fun!'
I honestly didn't mind listening to them except when they started asking me questions then comparing their life to mine as if they intend to 'win' at it or something. I still see some of these people, and personality-wise, it seems they never made it out of high school. Kind of painful to watch actually, reminds me of Napoleon's uncle from Napoleon Dynamite, always talking about 'the old glory days' never really having any interesting updates about current affairs.
I can see the use in talking yourself up on a date, maybe polishing some of your skills a bit and making interesting conversation, but I can't deal with people who brag about being the best and then falling flat, coming up short, or just plain failing at it. When I try to talk myself up I do it neatly, "I've tried my hand at video editing, and know a couple tricks." or "I frequent the gym, but I don't try to live there." Then again, I too, remain single so who know? Maybe it works for some people.