To respond to your post: I get how thats nerve wracking and I would probably feel the same. From your past experiences with him, does he usually talk a lot? Then he may have many conversational topics! If not, ask him all about Trinidad, ask him and his wife about what they do for work or their hobbies / day to day life in Trinidad, about their travels, about how COVID has been for them, etc.! Good luck!
Also, it wont let me message you back somehow because it says I need at least 15 of something and I only have 9 (posts I'm guessing) in order to message someone. So I am so sorry to disrupt your feed but this is the only way I can respond to your message:
Hi! Thanks for reaching out. I don't really know how responding works on here but I hope you can see this message. So, the context in which I am talking to these people i.e. what normally starts the conversation, and also whether these are work colleagues, class colleagues, family members etc: So with covid everything is way different but in the past it would be people in my class who I was trying to make friends with, people in clubs I joined like soccer and a cappella, and recently a few days ago, I joined a facebook soccer group game and I was the only girl so I felt a bit awkward. Also it is not always just strangers who I am first meeting. It can also happen with "kind of friends" or mutual friends where we know each other, hang out with similar people and in similar areas (i.e. roomates in the past), etc. Basically, my issue is meeting someone, and taking it further than small talk, and bring it to a point where I consider them a close friend where I truly can tell they care about me and things are comfortable. To answer your Q about what I would like in a close friend: I would like someone who truly cares about me, who demonstrates this with actions, texts, etc., someone who I can have good conversations with, who I can do fun activities with, and who I feel comfortable with. Of course, I would provide the same things to them. Oh okay when I get a chance I will check your posts out, thank you!!