My sister was raped by her boss, so maybe she is more sensitive, but she box and spend 6 hours a week at the gym (10 hours total if you count boxing), and truly attractive males hit on her daily. Any guy who hit on her without being prompted, even the 'cute' ones (which is, to be fair, a big part of gym goers), get on her 'red flag' list, that she share with her gym and box friends. Maybe when she was younger she might have thought that.
My personal experience (which was until recently limited to feminist hippies living in vans/tents and playing guitar around a fire tbh) is the same. Just have normal conversation, a bit of small talk, listen and pay attention, flirt a bit, only show off if it doesn't break the rhythm of the moment (better yet, don't show off at all), ask for a date without saying it's a date. If it's no, it's no. Doesn't mean you can't flirt anymore, flirting is always fun (and if it's not for you, think about that: more practice!).
It's really hard to do this well and not be boring however. You have to do all those things and also subtly telegraph that you're somehow attracted to them and don't just want to have "a normal conversation" - mostly by 'showing off' subtly enough, not looking like you're blatantly showing off. It can be done, but plenty of guys are going to try and fail. I do suppose it's better to look excessively boring and inoffensive than to end up on their "red flag, animal, unsafe to be around. Must be avoided" list.
Takes like these are very odd to me. The parent comment is basically saying to have a conversation and if it goes well ask the person out. If said person finds your conversation boring then why would you want to date them in the first place?
So much discourse online about dating is "I HAVE to do X and Y and Z and it's just exhausting", but why? Why go through all this effort if you don't want to? Isn't the whole point of dating to find someone who makes you happy and likes you for who you are?
Yes it is, that's the whole point. As a dude, you're not going to signal "hey I like you for who you are, I care about making you happy" with boring conversation. You need something that's not just that, and is not "keep pestering them and don't take no for an answer" either.
A conversation will naturally be interesting if two people are interested in each other, even if it's about a boring topic. That's what chemistry is. It may start out boring, but if there is chemistry, it won't stay that way.
But hey, that's just me. I have absolutely zero interest in "the game" and doing things I wouldn't normally do to get women to date me, and I am lucky enough that I don't have to. I just see people talking about doing all this stuff to get women to like them and I can't help but think that a relationship started that way is doomed to fail. I would find it exhausting to constantly worry about "signaling" things to someone to keep them interested. I want to be myself, always, and if they're not interested, oh well.