I think your therapist is approaching this the wrong way around. The better you feel about yourself with absolutely no regard for other people, the happier you are in your own skin, the more you appeal to others as a potential friend or mate. At least this is true for me.

It seems like he's trying to treat a symptom and not the cause. Like say you have allergies - he's giving you tissues to blow your nose, not giving you allergy shots so eventually you'll build up immunity and your nose won't run.

One other thought: how old is he? Is he still dating? What are his personal circumstances? You set up your profile with heavy input from him. It's entirely possible he steered you unconsciously towards what he would find attractive, which may not be what others find attractive. If you want to keep trying this, ditch everything you guys did together and make it all from you.