Quoting Charlie's Lovely Mommy:" You don't think it would make him upset though? And i mean what would dating even mean for us? Should ... [snip!] ... if we dated and it didn't work, than if we didn't try at all? I guess I'm just wondering if I should date this guy at all. "
Yes! Date! Live a little! Just prepare yourself for reality. Sometimes it works, and some times it doesn't. Don't over analyze it and over think it. I think a date alone wouldn't hurt anything. You can get to know each other, just be two mature adults IF it doesn't go the way as planned. Theres no shame in dating, and theres certainly nothing to be ashamed of if it doesn't work out. Just try not to over think everything, let it happen naturally and relax!