I posted a similar question when I was at the freaking-out side of starting to date again. I've now been out there since February, and I can tell you a little about what I've learned. First, you don't have to be at some ideal weight before you start dating. If people are asking, it's because they are interested. So go. Don't let weight or the band be a reason you hold yourself back. I'm starting to cross the line from full-figured into curvy, but I've got a ways to go before I'm really feel satisfied with my weight. Still, getting out there is good practice and fun. And the men who ask me out, think I look good now. I'm open with them about watching what I eat and going to a trainer or yoga classes. I can't eat bread at all, so I have to set up that I'm careful about my foods. But I don't make a big deal about it, and I don't tell them about the band. The few dates I did tell early on were not supportive. Some were very judgmental about my having weighed more or about my inability to lose it on my own. They saw the band as a show weakness and couldn't grasp just how much work it is . This taught me that there's no reason to share that until you really care about someone, and there's a better chance he'll be understanding.
I don't, however, schedule dates for 2 weeks after a fill, because as you can see from my signature I've twice had to have a filled backed out a bit, and I don't want to take a chance at not being able to hold down food.
Hope this helps you. Now get out there and have some fun with it.