I'm completely the same with having clothes in loads of different sizes. My biggest trousers were a 28 and I've got every size down to an 18, at the moment I'm 18 top and 22 bottom, so hopefully in the next few months will finally be able to get into them again!
I've never really lost a lot of weight before. I've done diets but only really stuck to them for a few weeks or something, nothing long term. I was actually quite happy in my own skin, even as a big girl, though obviously I wanted to lose some weight. For me the decision to join SW came when I found out I'd need to pass an occupational health screening to get onto my uni course in Radiography. I refuse to let my weigh stop me getting my dream job (I want to be a sonographer), so haven't looked back since last August. I've got a place on the course, just got to get through the occy health check in Sept, should be a LOT skinnier by then with a bit of luck, still nerve racking having that hanging over me though!
I've been with Chris for 2.5 years, we've decided not to go out this valentines day, but are off out the night before instead. I hate busy restaurants and this way we can get the same meal for half the price on the midweek menu, lol. Sounds cheap but I'm a student and only work part time so cheap is good!
I'm the same as you when it comes to suggesting the holidays and things. I'm absolutely addicted to travel, it's the one little luxury I refuse to live without. I don't drink, smoke or eat loads of fast food so when I have spare money it goes into travel plans! I guess I'm quite lucky that Chris doesn't have a huge desire to go anywhere, except Vegas and Austria, so that I get to pick most of the places!
On the other hand though he's music mad and always drags me to loads of different gigs, so I guess it works both ways. I'm definitely not the dominant one in the relationship, only when it comes to holidays!
Hope you manage to do something for V-day. I don't think it really matters so long as you spend the evening together, but I totally get that its nice when they do something romantic. Chris isn't hugely romantic either, but a few months ago he did send me flowers randomly one day. It was a complete surprise and so lovely. I did jokingly ask him if he'd cheated on me though or been hit on the head that morning!