Make him a coupon book :) 

I'm bad with gifts period. I'm the kind of person who doesn't ask or expect getting gifts every holiday, so when it came to buying something for the boyfriend I had, I was stuck. I always feel like i'm getting them something they don't want. 

I think a lot of people are bad at gift giving. It just comes down to what they like or what they want. I think we generally worry if they won't like the gift. I think unless it's a very cheap, not so much thought out gift, then they won't like it, but if you put some heart into it, they should like the gift. 

We have several agreements about gifts. For Valentine's Day, nothing over $20. Birthdays and Christmas are the only days we get big gifts for each other, and we generally agree on a price limit- sometimes very high ($1200 one year, the year he had just come home from a deployment) and sometimes low, $50, depending on what's been going on. For our anniversary, we don't do gifts, but that day is sacred to spending time with each other, nobody else.

find out if your SO has a favorite brand of scarves, purses, wallets, etc... Either buy small gift cards to build up to a bigger purchase that SHE wants to get or ask her to make it easy for you and pick out a few "items" on the "wish list" with (something like it) notes so that you can figure it out.

My fiance is horrid about gift buying. I listen when he points something out, I jot it down, I try to get it without him knowing about it, meanwhile discourage him to buying anything remotely alike the item himself because that'll just KILL me.

For ex: my fiance likes to cook and he's been living on his own long enough to do a great job in making dinners, baking a mousse cake by scratch or cookies! I am not, but I do buy him cast iron pans that he's been meaning to get, or a paring knife that he really wanted to replace his current one. But he had issues with buying what I would actually want and use on an ongoing basis... so I told him my favorite brand of PURSE is MK (michael Kors) and for the longest time, we did not have it locally available so my purses used to fly in from Texas. My first Christmas gift was my work purse; I LOVE IT, and it's not too common looking nor is it so pricey that he was broke for months. It was the summer season, so he bought me the smaller cream coloured purse for my birthday this year. Purses are great as gifts, as long as you keep your SO's personal favorite/tastes in mind FIRST. DO NOT get her any clothes or shoes unless she has tried on a few with you and you kept notes of sizes. Nothing is worse than ill fitting shoes or clothes from your signficiant other. Or take her out for a random picnic.

As for your SO's bday falling RIGHT a week after Vday, just bump them together. You've been dating 2 yrs, it's okay to bulk up the Vday present with a bday present. Believe me, once you get out of school and you're working 9/5, it's going to have to do. Take lots of pictures together, buy an album, personalize it with your own special touches, buy a calendar and mark all the dates with notes or happy faces, LITTLE things DO count. When I wasn't working a full time job, I used to bake at least once every week of his favorite baked goods. Cards always. Watching his favorite movies even though I HATE them. Learning to golf (he's a nut, pitch & putt will have to do), watching a play, and instead of DVDS, do an ACTIVITY together. :)

I try to make gifts different. Like, for Valentine's day I'll do something more sweet, like love letter, chocolate, stuffed animals, etc. Then for birthday or Christmas, I'd give/like things more personal to me, like for my boyfriend I got him music stuff cuz that's what he likes