Dating someone more/less attractive than you

I've been told countless times by people that my current boyfriend 'punched above his weight', and have even had a few strangers when we're on a night out ask me why I'm with him. This in turn has made him incredibly insecure and he's started to doubt our relationship, despite the fact that I'm completely in love with him and think he's beautiful. He's so indoctrinated in this state of mind though that I don't think he can see a future with me :( . Has anyone else had any experiences of dating someone who is not on the same level of physical attractiveness than you are? How did you overcome it? Or was it not even an issue to begin with?

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