Is this anonymous gift a good idea?

[AskMe]

Hi there. I really like my boss as a friend (ok, maybe a little more than friends). He is one of the nicest and most openminded men I've ever met because while many employers would find an excuse to fire me, he did not fire me for transitioning from male to female and instead said I had his support. Not just that, there are so many good things about him. He just told me he's going through a separation with his wife. I would like to leave him an anonymous gift because I want him to know that he is loved and appreciated by his people, especially during this hard time. But I don't want him to know the gift is from me because I don't want him to think I'm obsessed or creepy.

1) I'm thinking about getting him a Nook which is an Android-tablet made by Barnes & Noble. It will NOT cost me anything because I will be using my credit card's miles on it. The tablet is worth $100. I thought it would be a great gift because his cell phone is Android-powered and he travels a lot so I'm sure it would be nice to have a bigger screen to access Facebook, watch movies, read, etc. Is this a good gift or it's too much?

2) I refuse to use my name but should I add a short message saying something like he's a good person or just leave the gift blank? Should I leave it on his desk when everyone leaves or have USPS send the package to our workplace anonymously? If it's left on his desk, he'll know it's one of his workers. If it's from the mail, he could also think it could be one of his clients.

Thank you for any suggestion

[Daniel]

maybe if you can do it sneaky go 4 it!

[akluis]

Bad idea.

Even if you bought that Nook for $1.00 because 'it fell of the back of the truck' or with your miles, it doesn't matter, it has the APPEARANCE of a high end gift.

Giving your boss a gift that is more than $10 automatically will put you in the creepy/obsessed column by default. Doing it 'anonymously' states 'romantic interest with fear of rejection blocking a more forward move' or 'is being done by someone who knows this shouldn't be done and hence hiding'


If you like your boss as more than a friend, ask him out. (Or at least look up in your HR policies if dating like that is even allowed, often it is not)

If you want to thank your boss for being supportive buy him a coffee mug that says 'World's Greatest Boss' and put a post-it note on it saying 'Thanks for the support during my transition' and sign it. Because the gift is cheap and cheesy and unwrapped and not with a card it's significance is greatly downplayed and hence avoids the creepy vibe