Buying for men is HARD.  With a father, a brother, a fiance, and various other important men in my life to buy for this Christmas, its all I can do not to pull my hair out. That's in addition to all the important lady's presents, plus trying to make a list for myself so that I can avoid invoking the same hair-pulling-out feeling in others that is so overwhelming in myself.
But there are a few things I have learned when buying presents (and making lists) that make the whole process much smoother, and make for many less after-Christmas runs to the mall to return items that no one is going to actually use.
Rule #1: Know Your Giftee
Isn't it always easier to buy for people that you know well?  You can fake it when you know that a present from you is in someone's near future.  This doesn't have to be a one-on-one dinner where you discuss your hopes and dreams, but making a special effort to have conversations with the object of your gift-buying will steer you in the right direction of what to get. This is especially helpful with people that you are close-but-not-that-close with, such as in-laws and friends from the office.  Finding out what someone's interests are, even on a very surface level, can be a tremendous help when buying gifts.  They love Fight Club?  Get them the Special Edition DVD if it's a family/bigger gift, a bar of pink soap with the logo if it's your work Secret Santa.  Just knowing a little bit about a person can make a gift seem thoughtful and personal.
Rule #2: More Expensive Doesn't Mean Better
Depending on how well you know your receiver, you can get a present that they will enjoy just as much for less.  Don't feel like you have to spend x amount in order for your gift to be special.  Things on clearance and the occasional Big Lots find, if it's really something that they will enjoy, are just as valid as a big-ticket item from a department store.  The exception here would be if you know what the other person has gotten you.  Just for etiquette's sake, it's a good idea to try and spend around the same amount of money on them that they are spending on you.
Rule #3: Don't Sacrifice a Bird in the Hand for a Surprise

If your receiver has specifically told you what they want, get it! If they've shared it with you, then yes, they may be expecting it, but that doesn't mean that the giddy feeling of receiving a gift will go away just because they know what it is.  In fact, if you get something different when the person has specifically told you what they want, they may be disappointed that they didn't get the item they told you about.  If you must have a surprise as a part of your gift, add a little inexpensive something on the side to what they requested.  If the man wants a Red Rider BB gun, get him a Red Rider BB gun.
Rule #4: If All Else Fails, Gimmick It Up
You know what I got my little brother for Christmas this year?  A set of Jeff Foxworthy "You might be a redneck if" mugs.  Does he need them? No.  Will he love them? A resounding yes.  Unless there is a great demonstrated need for something/the person has told you specifically what they want, getting something functional and funny is a valid way to go.  Stress on functional: while funny figurines or posters will get a laugh upon opening, they'll probably end up in a junk drawer sooner or later.  Something like a mug or a t-shirt, however, will still be usable even after the joke has worn off.
Rule #5: Even Mediocre Gifts Can Have Nice Cards
If you have that difficult friend or relative that won't tell you what they want and who's interests may be hard to shop for, a basic gift can be dressed up with a nice card.  This also works if you're strapped for cash. For your girlfriends, a nice nailpolish with a handmade card works great.  Giving gifts is about showing love and appreciation for another person, and actually telling them with a card or letter is more efficient both in letting them know they are important and on your wallet.

And now that you know how to get something they want, here's how to get what you want!

List, list, list, list, list!
I am an obsessive list maker, so Christmas is my holiday in more ways than one. Making neat, numbered lists decorated with snowflakes just makes my heart smile.  Plus, having a list insures that the gifts you are receiving are things that you will use.  If you want to get really fancy, make a different list for every person who will be buying for you, tailoring shops and prices accordingly.
This gets super easy online these days, as lots of online stores have options to add their items to online wishlists!  My favorite site to do this on is Modcloth.  Not only is all the stuff SUPER adorable and in a variety of price ranges, but it has an option to email your wishlist to whomever you want!  Plus you can customize more than one wishlist, so you can organize items by price or type before you email the list.  I emailed mine to Caleb this year and I can't wait to see what he picks out :)

I just had to throw that in here.
It's easy to get caught up in the present aspect of Christmas, especially when that particular aspect is giving you headaches, but the season is actually about loving and appreciating family and friends, and, for me at least, faith and hope :)
Merry Christmas!

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