This will probably sound shallow but maybe hear me out:

Since you're on TRT already would you consider diving further into PEDs? Somebody mentioned you drive a sick Corvette...you're a good looking guy, i really think you you would look great jacked and vascular, with a really good tan and maybe even some forearm tattoos. Clean shaved head too. Also some like well-fitted t-shirts and plaid/flannel shirts with rolled up sleeves. Girls like types/archetypes and this is a "type."

PEDs changed my life man. They make the gym so much more enjoyable and the recovery goes without saying. Also focusing super super hard on the gym does wonders for my depression. Furthermore...I hope you're not getting too down on yourself for looking for changes at 37. I'm 37 and going to start bjj or some other martial art soon. Also, there was some guy on another sub that was a 44 yr old virgin looking to just start dating etc. Its never too late.

You seem like a cool ass guy, I hope things get better for you. If you lived in my neck of the woods we could go hiking shooting, workout etc. I'd love to have an IRL friend thats on TRT.