Jill gives Bob and his wife a $20K cruise, and says something to the effect of "Make sure you book your next cruise (on me!) for next year before disembarking--you'll get a great discount if you book while you are still on the ship!". While they are on the cruise, COVID 2.0 breaks out, tanks the market, and the value of Jill's assets plummets by 80% causing her to lose everything Bob has earned plus some of her principal

As soon as Bob and his wife arrive back from their cruise, what is the nature of the relationship between Bob and Jill? How confident is Bob that Jill--having lost hundreds of thousands of dollars, and having just spend 5-figures for a friend's cruise, with an implied promise of another cruise--will not turn around and sue him for an implied contractual relationship? Even if she doesn't prevail, what is the potential cost to Bob of dealing not only with the civil suit, but the potential for regulatory investigations and penalties on top of that?

Since we're in the Darkest Timeline, If I am only advising Bob, not only do I tell him “Don’t suggest or request anything” I tell him “Don’t even accept anything” In fact, the sooner he does this, and ends the relationship (in writing!), the better. Its great that he’s done well for his friend, but in a real sense, he’s been playing with fire, and he’s lucky he hasn’t gotten burned. Any sort of gift prolongs the nature of this potentially disastrous relationship even longer