Would you?

So yesterday I put up a picture of myself. This guy that's a family friend liked it (he's mom and my mom have been friends for over 20 yrs) i thought it was interesting hes never liked any of my stuff... anyways know he just moved down to my area. I kind of want to message him but I think it would be weird since we haven't talked or see him since I was a child. I don't have anything to lose. But I think I'd be weird... would you message him?