(soft chuckle) "uh...you sure this is a good idea? 'Cuz, uh...usually when you guys say that, things get real bad, real fast." (nervous)

Rica! uh- um- your outfit looks really nice today! Not that it doesn't always- I'm just gonna shut up now. (trying to flirt but wayyy too awkward)

Hey man...are you ok? You don't gotta talk about it, but- just know that i'm always here to listen (soft, gentle)