There were a few easy ways to start a conversation that ended in you two going to coffee, or exchanging numbers, he made multiple efforts, and probably felt like anything else was extra. Happens to everyone sometimes. The skill and art of striking up and continuing conversation is like 90% of dating/asking people out. Sometimes it frustrating, as you see some gorgeous woman, dope outfit, walking in the opposite direction, exchange maybe a quick glance, and what else is there to do? In your situation, same general space, both not at work, that's like 40% of the equation, not as ideal as a bar, or a party, or club, where it's expected that everyone's there to meet, but it's better then just straight on the same street at the same time.....So, then it's not about the logistics, but confidence and putting yourself out there, finding something to spark up a conversation.
