My dad gave me a crisp one hundred dollar bill for my 37th birthday yesterday along with the following caveat: "Don't spend this on groceries or bills. Don't put it in your savings account. Don't use it to save up for something else more expensive. Go treat yourself to something that costs around $100 and let me know what it was."
(FWIW, my dad gives me a hundred dollar bill every year for my birthday and I usually spend it on groceries or bills, put it in our general savings account, or apply it towards a larger purchase... right now I'm saving up for a fishing kayak.)
So since I hate to dissapoint my dad and since it has been a long time since I just went out and dropped a Benjamin on something for completely selfish reasons... what's the coolest thing you can buy/do/see for $100?
Rock climbing shoes, or a good harness.
A two hour massage.
Those collectible CDs you've always wanted.
The coolest thing is going to depend on who you are. Plenty of good suggestions that would suit many men have been made (good scotch, a nice steak dinner, a concert, etc...). To add a few of my own: seeing a good production of a Shakespeare play, a good knife, a day at the shooting range, go watch your favorite sports team, buy a stack of books, CDs and DVDs on Amazon...
Or go buy that item for your hobbies that you want but just can't afford. If you play electric guitar, maybe it's a certain effects pedal, you mentioned fishing--upgrade a pole or something (I know little about fishing), if you like to dress well get some nice ties or cufflinks or something, if you like to cook buy some kitchen equipment.
I don't know what your interests are, but there's almost certainly something you want but have been too responsible to buy. Well, your dad is giving it to you as a gift.
Alternately, I dunno what sort of experience (dinner, performance, sports) you might like, but consider whether you'd have more fun with another person, whether your wife if you're married or a friend.
I got the same thing from my parents back in January, with a similar set of orders. I didn't adhere to their wishes, and ended up spending the money on a jogging stroller for the family. I had initially earmarked it on some new waders, but just couldn't decide on which ones. I don't regret what I spent it on, but rather wish it would have been something solely for me.
I know that's probably of no help, but thought I would share. Good luck.