I am part of an expat group which goes out in various social settings, drinking, boardgames amusement parks etc, now I've always been the type of guy that has a lot of confidence and self respect, however I haven't applied that in my dating life yet, I've been focusing on my passion (combat sports) for a while.

I've recently started to go out more to learn and acquire a good social understanding of things and getting to know new people.

The thing is how would you guys who are much more experienced handle trying to advance a relationship with a newly known person who does give positive signals but should i try to push it to the next level in the case i get shot down that could ruin my reputation within the group since it's a sort of a taboo to "harass & make someone else uncomfortable" especially if it's a male female dynamic.

Of course i won't focus on one person in particular but understanding how to act in situations like this would benefit me in the long run

What i'm thinking that makes sense is simply to insert myself more in events that i like and if said person joins in (assuming it's only the boardgame setting) to try to test the waters in a semi direct way whether or not it's a match, I would be more careful at the level of sexual interest i make, but it would take a longer amount of time than what is deemed accettable by the standards of this subreddit

What's your take guys what would you do?