Here is one website you might want to secretly bookmark for your boyfriend/husband/dad/friend: http://GiftGirl.com. Just before the Holidays madness - GiftGirl couldn't find a better timing for re-launch, with the new improved tool to help the non-gifted gift givers. Gift Girl (who happens to be a real person and our dear contributor Jean V. Pratt) will suggest you gifts based on the type of girl, your budget etc.
Of course my first try with GiftGirl was picking a gift to myself (I know, it's called shopping, but I still love the idea of calling it self-gift-giving). After picking my budget ($200-500, why not splurging a bit on myself?), the type of girl (New York City Girl, no doubt) and describing myself as "fashion forward", I got about 200 results ranging from clothing to electronics.
200 items were a bit too much to my taste, I would expect the results to be a bit narrowed, although do appreciate the choice. Surprisingly, some of the items offered to me, I already own: the red Cube coffee machine by Nespresso is my favorite kitchen accessory (and the only I must confess). And the rest would definitely make a nice gift for the dear me: Tom Ford over-sized sunglasses, Marc by Marc Jacobs high waisted skirt, Pedro Garcia Ankle Bootie, Burberry scarf, Tarah Smith handbag and Louis Vuitton makeup bag. Spot on!
What concerned me that among those items was a Baby Basket (do I need another reminder that my clock is ticking?). My suggestion would be considering more questions narrowing down the results to avoid unpleasant moments like this. Age and marital status should be important to consider while choosing gifts.
Overall I had fun picking myself a gift, which makes me even more excited for the Holidays season. If only we all could avoid unpleasant gifts this year!