You want to lose weight, no? Here's your chance!
In my very humble opinion, the photo of you and Steve with the short hair lifted slightly from your face looks gorgeous and timeless.
The longer hair weighs your look down. It makes you look heavier. It has no style or personality - it simply hangs. Perhaps you should consider investing some money in how you look now instead of waiting to lose the weight. Think a bit Louise Hay - she takes amazing care of her appearance because she knows she deserves it! Hire a personal shopper and get gorgeous, beautiful feeling clothing (underwear, too!) and shoes. Go to a great hair salon where they use organic products like Aveda and let them advise you. Get an appointment to discover your color/type. Buy organic, environmentally sound makeup. Go for mani/pedis each month. And so on, and so on. Why shouldn't you have a budget for this?
As for Steve (since we are doling out the constructive criticism) - I am sincerely glad you have found more joy, light and love since that photo was taken because you looked miserable. The photo of you on the beach (Facebook) is the best I've ever seen of you. You radiate aliveness, joy and humanity. Light blues and turquoises suit you very well.
There ya go!