Last valentine's day I proposed to my (now) wife. I was super-low on money since I was saving everything I had to buy us a house (which I was able to do a month before we got married). She knew I didn't have any money so she said that she didn't want me to do anything expensive for valentine's day. I basically led her on saying I couldn't get a reservation anywhere, so we'd just get together at her place and I'd cook her dinner or something.
Anyway, Valentine's day was on a Friday which was payday so I had to do EVERYTHING on that day because I didn't have any money before then. On my lunch break I ran out and bought her engagement ring (she doesn't like diamonds and her favorite stone is garnet so I bought her a really awesome celtic-style ring with a garnet in it) and a matching necklace. I also picked up the flowers that I had specially ordered for her from a local flower place, and confirmed the reservations I got at the last minute at a local italian restraunt that she really likes. I had everything all set and picked her up, flowers in hand with the necklace laced into the flowers. I then started driving towards her place and at the last minute took a detour. After driving her around for a bit we pulled up at the italian place. We had an awesome early dinner (and bottle of her favorite wine), then headed back to her apartment. Before we went in I told her that I wanted to go for a walk along the river (which her place was on the bank of) so off we go. After a few minutes we're in a secluded place with a park bench so we sit down and she's telling me how great the day has been and how suprised she was with dinner, flowers and the necklace. After talking bit I tell her I have one more present for her and ask her to close her eyes. She takes a deep breath and closed 'em, and I did the whole getting down on one knee thing with the ring. I asked her to open her eyes and then asked her to spend the rest of her life with me. After crying and hugging and kissing she finally mustered the ability to say yes. 7 months later we're newlyweds, having been married since August 1st.
I think the first big romantic thing I did was pretty early in our relationship (3rd or 4th date), and was what really made her fall in love with me. We had tickets (already paid for) for the premiere showing of the new Star Wars movie (we're both big geeks) and she got really sick. She told me to go by myself and she'd stay home but instead I went over to her place and made her some chicken soup and just did what I could to make her feel better (backrub, etc). We had a great evening even though she was sick and we missed Star Wars. Later we went and saw it and realized that we didn't actually miss anything at all, it sucked so bad.
Jason