Most Helpful Guys
I'm sure you have a chance with him but you have to ask yourself is that something you really want to do cuz if it doesn't work out his mother's day your best friend you might have issues because of that and you still might have to be around them so you might want to think that through before you do it. I have a rule and my rule is I won't date any of my friends relatives for that particular reason so think it over if you feel like it's something you can handle in the event it doesn't work out and you're still thrusted into situations with this guy then by all means do it but if you feel like that's something you can't handle then don't do it
My parents are 12 years apart. The age gap isn't an issue. Before you go after the brother you should work on the assumption that your friend has a thing for you and until you are 100% sure that he doesn't then don't bother with the brother at all. If you ruin the relationship with your friend chasing his brother then even if it works out with the brother you'll be stuck with a resentful brother in law. The older brother might also reject you in favor of his relationship with his brother. Avoid messy love triangles.
Most Helpful Girl
Don't say ANYTHING Here, dear, Try and Flirt With... My Best Friend's Brother. Although, With his Bro, It could be a Territorial Deal with What you Feel. Your Bestie could Feel a but like a Cat on your Turf. Not romantically, Mind you.
If he Responds to your Flirtations, Go Slow with Joe. If Not, He doesn't Find you Hot. xx