Congrats on finding an old love! What a good feeling!
For me, in my mind I planned on switching to bike shorts when I lost x amount of weight. Then realization set in. The more I bike, the more I eat, so I don't really loose any weight, but I sure do feel sooo much better! Since I realized this, I switched when I just got tired of the sore tush and wanted the padded shorts.I have a pair of the baggy ones as well as the others and depending on my mood, I decide which ones I feel like wearing in public.
Good luck!