"Why wouldn't you travel by main roads?"

Episode 2, Four Marks - Jaskier

And now, Jaskier's turn.

We are introduced to Jaskier loudly singing in a tavern, being told to shut the fuck up and pelted with food, and snarking back, "I'm so glad that I could bring you all together like this."

He then notices that wait, he's failed at bringing absolutely everyone together because that one guy in the corner is sitting staring at his table instead of paying any attention. Just as cats are drawn like magnets to people looking away and holding very still in the hopes they'll be left alone, Jaskier beelines for this stranger.

Is this a sign Jaskier is a free spirit with no sense of self-preservation? No. Jaskier just illustrated he doesn't mind a certain amount of pushback, his very career involves putting yourself out there a lot, and they're in a crowded room making it the safest place to do something like this. Even if Mr. Quiet reacts badly to Jaskier bugging him, Jaskier can probably just skitter back unharmed and call it a wash. (Also worth pointing out - I'm not saying Jaskier's good in a fight, but he's not actually a teeny guy. He's barely shorter than Geralt. That's going to discourage people from starting unnecessary fights when they could just accept he's leaving.)

"I love the way you just sit in the corner and brood."

Is Jaskier hitting on Geralt? Eh, yeah maybe. We'll find out in a moment he did not at all recognize Geralt or even the fact he is a heavily armed man, so it can't have been that he knew Geralt had to be interesting as a witcher. All he knows about Geralt right now is there's a big guy in the corner not paying attention to him, so "wow, he's hot" is as good an explanation as any.

Also interesting is that Jaskier is more or less introducing himself with, "So I noticed you seem to want to be left in peace but that is not going to stop me."

Geralt: "I'm here to drink alone."
Jaskier: "Good. Yeah, good."

I think people often think "risk-taker" and "fearless" are the same thing, but really, a person who engages in risky behavior usually has a very good sense of danger. Jaskier doesn't go right up to Geralt, he initially stands back and partly behind a pillar, and when he goes closer he remains standing. He's feeling out the situation. And if Geralt did react poorly, he wouldn't be able to reach Jaskier and Jaskier would have a clear space behind him for a quick escape.

Which is to say, Jaskier knows how far he can push people, knows the signs the other person is going to push back, knows how situations go south, knows how to mitigate that, and does this because he's weighed all that and decided the odds here are acceptable. He doesn't keep singing when people start yelling, but he does keep bugging Geralt because Geralt's objection here is so far a toothless one. Geralt is a big guy but isn't displaying any sign of violence and is instead desperately continuing to not make eye contact, so whether or not he currently wants Jaskier there, he's going to put up with him for now. Maybe Jaskier will win the stranger over, maybe the guy will get so annoyed he ends up needing to skedaddle, but so far it's good.

And so, Jaskier gets in front of him, then when Geralt continues to not react with more than a sort of exasperated defeat at the general concept of socializing, sits down.

"No one else hesitated to comment on the quality of my performance, except for you. Come on. You don't want to keep a man with bread in his pants waiting."

That all said, how long has Jaskier been doing this? Not long, I'd think, with how awkward he is. Part of his chirpy behavior earlier may be that all of this is still pretty novel and exciting, and similarly, that may be why he's viewing this as a situation worth the risk. Even being rebuffed is a fun new experience. He's eighteen at this point and given he actually got an official bardic education, he must've left the academy relatively recently.