Good evening, Rob, and thank you so much for your question. I realize it is difficult to reach out for help. Please know I honor your courage.
Ahhh yes, dating can be difficult and I certainly understand how it's especially challenging for those who struggle with shyness. I commend you for continuing to put yourself out there and would love to offer some questions that can lead to some great conversations. You might want to try some of these....
"What are some of the things you love most and are passionate about? How do you find space in your life for incorporating these things?"
"If you won the lottery tomorrow, how do you imagine your life to be different? Would you make changes? Would you give some of your money away and if so, to what causes?"
"Where do you find strength when your world feels like it is crumbling around you? Do you believe in any philosophies or religions that give you strength?"
"Tell me a bit about your family...." "Are you close to your siblings?" "How are you and your siblings similar to each other or different?"
"What qualities do you possess that you really appreciate about yourself?"
"In what areas of your life so you struggle?"
"Explain more about your profession..." "Do you love it?" "How did you arrive at this place in your career? "What was the path that led you there?"
"Have you traveled? If so, what are your favorite places to visit? If you could take a trip tomorrow, where would you like to go?"
"Have you even done something you later found out made an enormous impact although at the moment it seemed small?"
"Do you believe we are put on this earth with a purpose or plan? If so, what do you believe your plan is/includes?"
Does this help you in any way? Perhaps give you some ideas? Have I answered your question? Is there anything else I can do to assist you further? I want to ensure you are pleased with my service. I also gently request you provide a star rating for me. Of course, we can continue to talk after the rating is provided.
Please take good care of yourself and feel free to contact me with any questions you may have.