Is this anonymous gift a good idea?

[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