The thing is dating, like any social interaction, involves some degree of awkwardness and chance. Openness to new people is really the only way to connect with others and it involves trial and error. I think it is perfectly appropriate for a therapist to point this out.

This isn't dating advice so much as an observation about interacting with one's world: if you want friendship or romance or employment for that matter, you need to go seek it. A likely place to find a job is on a job site. A likely place to find a date is on a dating site. It makes sense to look where people are offering.

It also makes sense to go into each interaction with low expectations and an open mind.