What kind of therapy are you doing with your T?
It sounds like, as you recognise yourself, you need to work on you self esteem. Notice the negative automatic thoughts and unhelpful thinking styles and start to challenge them with your T.
I had terrible self esteem prior to my most recent therapist, but we spent a long time going through that process- we worked on identifying negative core beliefs and challenging them. On repeat. Every week. It was hard, but totally worth it.
That doesn’t mean you can’t connect with people in the mean time. But be yourself, not who you “think you should be”. It’s not all about status and what you do in terms of job etc. it’s who you are.
Being vulnerable is how we truly connect. Asking questions, being interested in someone.

Also, try not to judge, even if someone has had a lot of one night stands. We all have our reasons for doing things and for coping with things, even if they aren’t the healthiest of ways. I guarantee there is more to that reason than just “she liked sex” or whatever. It’s important to be mindful of that.

Anyway, all the best with things