Selecting the right gift for your significant other is difficult because there are many factors to consider to avoid awkwardness. You should avoid risk, and communicate openly about exchanging gifts. If you "wing it," you might make a mistake.
Here are some guidelines for shopping for your significant other during the holidays:
Do NOT use "controversial" packaging. An example of controversial packaging is putting something significantly cheaper, or something other than jewelry in a recylced Tiffany box. You give them the idea that something expensive is waiting inside, so they're disappointed when it's not what they expected. My biggest error was giving a girl clothing in a Lane Bryant box I found. I didn't get it at Lane Bryant- in fact, I didn't even know what Lane Bryant was. I certainly learned about Lane Bryant the day the girl opened the gift though.
DO bring a friend along to keep you sane. When we are left alone to our own devices, we talk ourselves out of good judgment. It's easy to get wrapped up in the holiday spirit and convince yourself that weird wonderful thing you're considering is a no-miss gift. Bringing a friend along to bounce ideas off of and talk you back into reality is a good safety net.
DO NOT go too big, or too small. The easiest way to avoid too big or small is to talk about it beforehand, and perhaps set budget limits. When you get something too big, it overwhelms the recipient, like the time my sister's boyfriend gave her a trip to Italy. This might force the recipient to reconsider their stake in the relationship. My sister broke up with her boyfriend because the gift scared her (of course, she did make sure to go to Italy before the breakup). Too small makes someone feel under appreciated, and makes them feel stupid because your too small gift makes their gift look too big.
DO discuss whether you're exchanging gifts or not. If you started dating any time after September, you're in that weird abyss of not knowing if you're doing gifts for the holidays. If you don't talk about it, and you make the risky move of buying a gift on your own, it's usually not good. You'll get the old: "Oh...I didn't know we were doing gifts this year..."
DO NOT give "get-a-clue" gifts. A "get-a-clue" gift is a gym membership, diet materials, etc. The holidays are not a time to identify someone's weakness and improve them your way. In addition to "improvement" get-a-clue gifts, there are "replacement" get-a-clue gifts. If you can't stand that comforter he still uses from college, you might get him a new comforter. This gift says "I need you to change that disgusting thing on your bed." If you hate their wardrobe, you might clue them in by giving them replacement clothes. Speaking of clothes...
DO triple check sizes. I am a 34 waist instead of a 33, which makes me feel disgusting. My mom still thinks I'm a 32 so I feel super fat when she buys me clothes. I once tried to give my sister a dress. I hadn't heard of any girl size since my very first girlfriend. I remembered she was a size 6. I figured my sister was the same. Upon opening it, she ignored everything but the "size 6" on the tag exclaiming: "Geeze, I haven't been a size 6 since high school...ugh." And of course had I gotten her something too big, she'd ask me if she really looked that big. Just do your homework and make sure you're at least close.
DO communicate with their family members and friends for ideas. As the holidays approach, families and friends chatter about wish lists frequently. Not only will your significant other appreciate that you took the time to research, you can do a little bonding with their family in the process.
DO NOT give racy gifts. I refrain from giving racy items like lingerie. It could be perceived as a "get a clue" gift, and I might look like I"m only interested in things that go on in the bedroom. And please, if you do racy, make sure it's not opened in front of the family. Awkward!
What rules do you follow when shopping for your significant other, and what do you think of mine? What solutions do you have for holiday gift-giving quandaries with your significant other. What's the best and worst gift you've given and/or received to/from someone you've dated? If I don't know a woman's size, is it better to get something too big, or too small?
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