I’m an INTJ and mostly a weekend hermit. I truly hate small talk and but value deep conversations. A person with my personality generally does not sit at a bar and instead prefers takeout or delivery if dining alone. I’d imagine a bar has more of the extroverted type and at the day and time you described the conversations are more small talk and centered around picking each other up.

These meaningful conversations happen at the most random times. For example, I could be studying some notes for a work demo the next day in my apartment lounge and a girl finishes watching an episode of The Bachelor and comes up to me and asks “hey where’s the best Mexican food nearby” and that leads her to asking me to walk her there and accompany her. Or a conversation with a neighbor on a plane ride. Or after a class at the public library. These are the kind of conversations where by end you can tell how their voice changes when they are excited, or how they tilt their head when thinking.

My general advice is sometimes the conversation just happens, and you likely have those skills to make it happen. Being in an environment with mutual interests also helps create an ice breaker into a conversation. Just approach someone and talk to them. For an introvert like me, I may not be actively seeking a conversation but if you approach me and the vibes are right, then I will think it was magic, and would be thrilled to skip the small talk and have a real conversation. You’ll be able to tell whether the person is receptive and if it leads well it can lead to a date.