It takes a lot of time to get back in shape and the older we are the longer it takes. Personally, I wish there were hardly any mirrors at the gym, yoga studios, etc. -- ignorance can be bliss while it lasts and reality sucks! Stay committed to the fight! Never miss a day (working out). You will get there eventually.
Plus, are any of your meds making the fight harder? If there are, is it possible to change?
I am female but when I was single, I was definitely asked out more when I was in shape. I feel more confident about how my clothes fit when I get my weight closer to where it needs to be. I think confidence makes it easier to connect with other people.
So keep up the good work, working out. You can do it! It just takes time.