Experienced daters often use a combination of flirting, humor, and subtle sexual innuendos to create a successful connection when initiating sexting. This can include exchanging playful messages that hint at something more intimate and gradually building up the intensity as you both become more comfortable with each other. It's also important to establish trust and mutual respect before engaging in sexting, so that both parties feel comfortable expressing themselves without worrying about being judged or making the other person feel uncomfortable.