I'm 36. It worked with 5ish women before I met my wife (worked with her too) while dating in my 30s. The sillyness is in some ways the point. Don't take it too seriously, and only ask if you know the answer. Humans give lots of social cues when they want to be intimate: eye contact, smiling, touch, scooting closer, flushed cheeks, incidental contact of the knees or hands. Read those cues correctly and it won't really matter what words you use because you will already know they want to. And humor is attractive.
For whatever reason, probably societal conditioning, women tend to expect the man to initiate intimacy. It's scary and nerve-wracking and a lot of pressure. But just throw this line out there. The worst thing that can happen is they say no thanks and you move on.
I've found that women, even and perhaps especially adult women, enjoy playfulness, fun, and jokes. The world is serious and difficult. Dating can be a huge pain in the ass. Finding a partner that makes you laugh is often one of the top things women are looking for in a partner.