Love: Gift and Especially Close Group

I have been dating my boyfriend for just over a year now. Our relationship has had its bumps, having always been long-distance, but when we're together we're both so happy. He's never been good at being romantic, and I realize that we're both still learning how to be in a committed relationship. For past holidays and special occasions, he hardly did anything. Last month was our one-year anniversary and I was so excited. By this point in our relationship, I had expressed my feelings to him about being somewhat disappointed in the past. He reassured me he would do better. Once again I was disappointed by the lack of anything, and because of that we got into a huge argument.

We were back to normal, and then it was my birthday. He did nothing but wish me a happy birthday. His birthday was just days before mine. I drove seven hours to see him and worked so hard to make him feel special and loved. Today, I feel sad under-appreciated. I don't know how to react or approach this matter with him.

Christmas is just around the corner. I got him a gift I'm sure he'll like, but I'm worried that I'll be disappointed again. These unsure feelings take all the joy out of gift giving/receiving. What do you think?

– Disappointed Birthday Girl, NY
Your best bet is to plan these holidays together. Talk about how you'd like to spend a special occasion, get his input, and then figure out how to execute the plan. Maybe for Christmas your gift to each other could be splitting an awesome hotel for a night. Come up with an idea and then figure out who does what to make it happen.
Holiday apathy is forgivable (some people are just bad at this), but only if he's a kind and giving person on all other days. He doesn't have to spend big money -- he just has to be excited about making you feel good.

Try planning as a twosome, and start paying attention to his generosity. Gifts aren't a big deal, but it's important that you feel celebrated. If you don't, this isn't going to work.