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Rising Star
Nothing? I would feel pretty weird about my friend getting me a gift let alone an expensive gift.
More natural to me would get a couple of guys together and do a guys night out… super nice steakhouse, maybe some cigars. Pay his way. Just a good night with the guys but still a gift.
take him out for a Boyz night out. probably needs a break from taking care of the young ones.
Something monogrammed in leather or gold (assuming Super Bowl tickets are out of the question).
Johnny Walker Blue Label
You’re a generous friend to what sounds like a generous person. I might get him something modest that he might not get himself (e.g. football memorabilia) and then assuming he’s got on, make a contribution to a 529 for his kids?
Alternatively, could you get tickets for a football game together for the fall with commitment to foot bill for meal and childcare?
A lap dance at the local gentlemen’s club.
Depending on your budget, a nice watch (below are in the 500-1k range)
Tissot PRX
Tissot Gentleman
Seiko SPB 167