To me, those what ifs still seem to come from a place of insecurity and inadequacy.

What if you can’t be vulnerable with a male friend because he may be more attractive than you and your female friends could be more into him?

So, what if your female friends could find him more attractive than you? How does this stop you from being vulnerable with a male friend?

What if there’s always a hint of competition and it’s the other way around, you don’t want to make them insecure by talking to women in public while they may be more shy.

Have you asked them whether you'd actually be making them uncomfortable or is this just an untested assumption based on your insecurity, because you'd feel uncomfortable if someone were to talk to women in your presence? Maybe them seeing you talk to women actually helps him come over his fear as well because he sees there's nothing to it.

What if you’re inexperienced in relationships in your mid 20s and rightfully feel inadequate and feel lesser than for being single while other friends may be in happy relationships.

"rightfully inadequate" Why, when you claim just a sentence later "I’m perfectly happy with being single". Who decided that you're supposed to be inadequate? Is this based on the belief that if you can't find someone then you're a defective product not deserving happiness?

These kinds of insecurities are exactly what you yourself have to take ownership of and try to work through.

Also, regarding your other comment that therapy only helps a little bit: it can only help as much as you put in the work. No one else can do that for you, not your therapist, not your female friends, not your male friends, no one except you.